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Carbazole-based molecules play a significant role in dye-sensitized solar cells (DSSCs) due to their advantageous properties. Carbazole derivatives are known for their thermal stability, high hole-transport capability, electron-rich (p-type) characteristics, elevated photoconductivity, excellent chemical stability, and commercial availability. This review focuses on DSSCs, including their structures, working principles, device characterization, and the photovoltaic performance of carbazole-based derivatives. Specifically, it covers compounds such as 2,7-carbazole and indolo[3,2-b]carbazole, which are combined with various acceptors like benzothiadiazole, thiazolothiazole, diketopyrrolopyrrole, and quinoxaline, as reported over the past decade. The review will also outline the relationship between molecular structure and power-conversion efficiencies. Its goal is to summarize recent research and advancements in carbazole-based dyes featuring a D-π-A architecture for DSSCs. Additionally, this review addresses the evolution of carbazole-based hole-transport materials (HTMs), which present a promising alternative to the costly spiro-OMeTAD. We explore the development of novel HTMs that leverage the unique properties of carbazole derivatives to enhance charge transport, stability, and overall device performance. By examining recent innovations and emerging trends in carbazole-based HTMs, we provide insights into their potential to reduce costs and improve the efficiency of DSSCs. [ABSTRACT FROM AUTHOR]

The study explores carbazole‐based organic molecules as transport layers in durable perovskite solar cells, focusing on their optoelectronic and charge transfer properties. Thirteen carbazole derivatives are systematically analyzed via density functional theory (DFT) calculations to understand their structure and optoelectronic characteristics. Substituents like bromo, phenyl, thiophenyl, and pyridyl at positions 3,6‐ and 2,7‐ of carbazole were studied. Phenyl and thiophenyl substitutions lowered highest occupied molecular orbital (HOMO) energy levels, while bromo and pyridyl increased them, tuning HOMO energies from −5.45 to −6.03 eV. These energies align well with perovskite materials valence bands, with absorbance primarily below 400 nm, complementing perovskite absorption. The compounds showed high light‐harvesting efficiencies (LHEs) (0.22 to 0.94) and improved radiative lifetimes. Theoretical investigations identified most compounds as effective p‐type hole‐transport materials (HTM), except 3,6‐ and 2,7‐dithiophenyl carbazoles, which exhibited n‐type behavior due to low hole reorganization energies. Overall, the study highlights computational design's role in developing carbazole derivatives as promising charge carrier precursors for perovskite solar cells. [ABSTRACT FROM AUTHOR]

Carbazole derivatives are vital in medicinal and materials chemistry, yet accessing diverse substitutions remains challenging. Here, we introduce a regioselective approach for C1 and C8 alkynylation of carbazoles via palladium‐catalyzed C−H activation. This method provides a direct route to mono‐ and di‐alkynylated derivatives, addressing the scarcity of alkynylated carbazole‐based materials. Our study broadens the synthetic toolbox for carbazole functionalization, offering potential applications in optoelectronics, bio‐imaging, and beyond, while contributing to developing sustainable C−H activation methodologies. [ABSTRACT FROM AUTHOR]

Harvesting triplet excitons of heavy atom‐free purely organic chromophores under aerated conditions is challenging due to the quenching of long‐lived triplet states by molecular oxygen and vibrational dissipation. Herein, we show a supramolecular approach of triplet harvesting via mitigating quenching pathways of a triplet harvester. Specifically, we used a host–guest system based on 2,3 : 6,7‐naphthalene bis(dicarboximide)‐derived cyclophane (NBICy) and carbazole derivative (EtCz). Complexation studies and single‐crystal X‐ray analysis showed the formation of a rigid host–guest complex (K≈104 M−1 in CCl4), resulting in triplet‐exciton stabilization under aerated conditions via mitigating vibrational interference and oxygen quenching. Photophysical studies elucidate the delayed fluorescence emission from the charge‐transfer state (1CT) with a quantum yield (QY) of 6–8 % under ambient conditions which increased up to 36 % in an inert atmosphere. [ABSTRACT FROM AUTHOR]

Polycyclic heterocycles are the most common and critical structural motifs found in a variety of natural products, medicines, fertilizers, and advanced materials. Because of their widespread use in biologically active compounds and material chemistry, functionalised dibenzo heterocyclic compounds, especially dibenzofuran, dibenzothiophene, and carbazole derivatives, garnered much attention over time. Scientists are especially interested in elucidating more efficient techniques for developing these industrially essential compounds. Dibenzo‐fused heterocycles can rapidly be synthesised using highly efficient transition metal‐catalysed strategies as well as by economic metal‐free reaction conditions. This review includes a detailed overview of the most recent significant synthetic techniques, both metal‐catalysed and metal‐free, to produce these industrially significant and medicinally important dibenzo‐fused heterocycles. [ABSTRACT FROM AUTHOR]

Carbazole is an aromatic heterocyclic organic compound consisting of two fused benzene rings and a pyrrole ring and is a very valuable building structure for the design of many compounds for use in various fields of chemistry and medicine. This study presents three new carbazole-based thiazole derivatives that differ in the presence of a different halogen atom: chlorine, bromine, and fluorine. Experimental studies and quantum-chemical simulations show the effect of changing a halogen atom on the physicochemical, biological, and linear and nonlinear optical properties. We have also found that carbazoles C-Cl, C-Br, and C-F exhibit high tyrosinase inhibitory activity, with IC50 values in the range of 68–105 µM with mixed mechanism of action. Finally, molecular docking to the active site of Concanavalin A (ConA) and bioavailability for all compounds were evaluated. [ABSTRACT FROM AUTHOR]

The development of polymer‐based luminescent materials with efficient and switchable ultralong organic phosphorescence (UOP) under ambient conditions is of great importance but remains challenging. In this work, three new organic luminogens have been developed by attaching the ethyl benzoate to the nitrogen atoms of carbazole, 7H‐benzo[c]carbazole, and 7H‐dibenzo[c,g]carbazole via the Buchwald‐Hartwig coupling reaction, respectively. Subsequently, they are embedded into epoxy polymers through doping into the mixtures of bisphenol A diglycidyl ether and 1,3‐propylenediamine, followed by a thermal curing reaction. It is found that the resulting polymer films EB‐BCz@EP and EB‐2BCz@EP show unique photoactivated UOP properties. After UV light irradiation, their phosphorescence quantum yields are up to 7.6%, and the lifetimes reach 1.84 and 1.18 s, respectively. These observations suggest that it is possible to elevate the UOP lifetime without reducing the phosphorescence quantum yield by tuning the molecular structure of the guest luminogen. Upon thermal annealing, the photoactivated polymer films can recover to the pristine state, demonstrating switchable UOP characteristics of the polymer films in the air. Inspired by these exciting results, the EB‐2BCz@EP has been successfully explored as a transparent polymer film for erasable light printing. [ABSTRACT FROM AUTHOR]

Fused polycyclic aromatic compounds containing carbazole and diazapyrene skeletons as electron donors and acceptors, respectively, were synthesized in a few steps from readily accessible starting materials. The incorporation of diazapyrene units into the polycyclic compounds resulted in significant bathochromic shifts in their absorption and emission bands compared to those of the corresponding carbazole derivatives. Electrochemical measurements and density functional theory calculations were performed to gain further insight into their electronic properties. Our findings demonstrate that the incorporation of nitrogen atoms and substituents, as well as the different topologies of the fused‐ring system, exert a profound effect on the electronic properties of the polycyclic compounds. [ABSTRACT FROM AUTHOR]

We report a bioinspired approach to tune surface nanostructures by soft‐template electropolymerization in micellar conditions. Monomers highly favoring π‐stacking interactions are particularly interesting for favoring the polymer deposition in one direction. Here, original triphenylamine‐based monomers di‐substituted by thiophene and carbazole are investigated. Conjugated building blocks monomers are tested to favor deposition vs polymerization, even if the monomers are not perfectly planar. The carbazole derivatives have a much higher electrodeposition capacity than the thiophene derivatives, which is unexpected if thiophene and carbazole are taken alone. Moreover, in all electrodeposited films, monomer seems to be present as shown by cyclic voltammetry experiments, confirming previous works. The amount of monomer vs oligomers is highly dependent on the investigated monomer. For the resulting surface structures, hollow spheres and nanoribbons are particularly formed with some investigated monomers by cyclic voltammetry while nanotubes are observed at constant potential. The formation of nanotubes indicates a polymer growth more favored in one direction. These surfaces are less hydrophobic (water contact angle up to 111.5°) compared to films with spherical nanoparticles but these results can be explained only by the presence of air inside the surface roughness. [ABSTRACT FROM AUTHOR]

Background: Carbazole-based molecules containing thiosemicarbazide functional groups are recognized for their diverse biological activities, particularly in enhancing therapeutic anticancer effects through inhibiting crucial pathways. These derivatives also exhibit noteworthy antioxidant properties. Objectives: This study aims to synthesize, characterize, and evaluate the antioxidant and anticancer activities of 18 novel carbazole derivatives. Methods: The radical scavenging capabilities of the compounds were assessed using the 2,2-diphenyl-1-picrylhydrazyl assay. Antiproliferative activities were evaluated on MCF-7 cancer cell lines through viability assays. Additionally, the modulation of the PI3K/Akt/mTOR pathway, apoptosis/necrosis induction, and cell cycle analysis were conducted for the most promising anticancer agents. Results: nine compounds showed potent antioxidant activities with IC50 values lower than the positive control acarbose, with compounds 4 h and 4y exhibiting the highest potency (IC50 values of 0.73 and 0.38 µM, respectively). Furthermore, compounds 4o and 4r displayed significant anticancer effects, with IC50 values of 2.02 and 4.99 µM, respectively. Compound 4o, in particular, exhibited promising activity by targeting the PI3K/Akt/mTOR signaling pathway, inhibiting tumor survival, inducing apoptosis, and causing cell cycle arrest in MCF-7 cell lines. Furthermore, compound 4o was showed significant antimicrobial activities against S. aureus and E. coli, and antifungal effect against C. albicans. Its potential to overcome drug resistance through this pathway inhibition highlights its promise as an anticancer agent. Molecular docking simulations supported these findings, revealing favorable binding profiles and interactions within the active sites of the enzymes PI3K, AKT1, and mTOR. Moreover, assessing the druggability of the newly synthesized thiosemicarbazide derivatives demonstrated optimal physicochemical properties, further endorsing their potential as drug candidates. [ABSTRACT FROM AUTHOR]

Lipid droplets (LDs) dysfunction is closely associated with a multitude of diseases, including nonalcoholic fatty liver disease (NAFLD). Therefore, it is imperative to develop fluorescent probes that specifically target LDs for the early detection and diagnosis of NAFLD. In this study, a series of lipophilic fluorophores CZ1-CZ4 that feature a D-π-A configuration were designed and synthesized based on the carbazole and tricocyanofuran derivatives. The photophysical data revealed that all four probes exhibited large Stokes shifts (~ 120 nm) in high-polarity solvents (e.g., DMSO) and demonstrated enhanced fluorescence in solvents ranging from low-polarity (e.g., 1,4-Dioxane) to high-polarity. Notably, by utilizing probe CZ1, we could specifically visualize LDs and captured high-quality images, even eliminating the need for a time-consuming wash procedure. Moreover, CZ1 enabled monitoring of LDs dynamic changes in-real time within live cells, and importantly, it could be used to effectively distinguish normal and NAFLD tissues at both the organ and in vivo level. This exceptional property of probe CZ1 provides a practical tool for the diagnosis and intervention of NAFLD. [ABSTRACT FROM AUTHOR]

Objective/Background: Carbazole derivatives have a tricyclic skeleton, consisting of a central pyrrole ring fused with two benzene rings. Carbazole derivatives are an important class of nitrogen-containing heterocyclic compounds that are widely found in nature and in synthetic source. These heterocycles possess a wide range of bioactivities and some of them have been marketed as drugs for the treatment of various diseases. Although some review articles on carbazole alkaloids have appreared in the literature, they are quite outdated. The current study offers a comprehensive review on the isolation and bioactivities of carbazole alkaloids within a decade. The article might be useful for chemists who work in alkaloid chemistry as well as pharmaceutical area. Methods: ' Carbazole alkaloids' was the most useful keyword to search for literature data. References have been collected from various resources such as Google Scholar, SciFinder, and PubMed. More than 70 electronic publications were obtained from these resources. Results: More than 230 carbazole alkaloids have been isolated and structurally elucidated from different sources. Carbazole alkaloids possess a wide range of bioactivities, such as antimicrobial, antiimflamatory, anticancer, neuroprotective properties activities. Conclusion: In this review article, we have summarized 66 studies on isolation and bioactivities of carbazole alkaloids in the literature. More than 230 carbazole alkaloid compounds have been isolated and identified. In addition, the article also gives an overview on bioactivities of carbazole alkaloids. [ABSTRACT FROM AUTHOR]

Abstract Background Carbazoles are an important class of heterocyclic aromatic compounds that contain nitrogen atom in the ring. They have a large-conjugated system, attractive “electrical and charge-transport properties”, and the ability to efficiently incorporate different functional groups into the structurally inflexible carbazolyl ring. Main text Carbazole derivative ECCA acts as an anticancer agent by reactivating the P53 molecular signaling pathway; similarly, some other derivatives of carbazole show antifungal activity by acting on the RAS-MAPK pathway. Carbazole derivatives also show their effect on inflammation by inhibiting the p38 mitogen-activated protein kinase signaling pathway by stopping the conversion of DAXX protein into ASK-1. By modifying the AKT molecular signaling pathway through boosting protein phosphatase activity in the brain, they show anti-Alzheimer’s activity and also by translocating the GLUT4 these are effective against diabetes. Conclusion After exploring the literature on carbazole, it was found that carbazole has an immeasurably great potential for the treatment of various diseases as the carbazole nucleus leads to various synthesized derivatives which are used for their pharmacological activities. So there is a need to explore carbazole for some newer drugs.

Multi-stimuli responsive polycyclic aromatic hydrocarbons offer advantages of high selectivity, sensitivity, and versatility as they can integrate multiple inputs and outputs to achieve the desired applications in a flexible manner. In this context, carbazole and its derivatives have been extensively studied due to their tunability, outstanding electrochemical properties and good environmental stability. However, most of the studies used the polymeric forms of carbazole derivatives which requires energy-intensive synthesis. Recently, it has been reported that the self-assembled monolayers of carbazole derivatives offer more advantages over their polymeric forms in terms of stability and efficiency. Herein, we introduce a carbazole-based low molecular weight gelator achieved with synthetic ease, exhibiting a multi-stimuli response behaviour, i.e. sensing of cyanide ions and electrochromism, in its solution state. Further, the compound forms a gel in dioxane–H2O and DMF–H2O mixtures and exhibits aggregation-induced emission (AIE). The mechanistic pathways of sensing have been investigated and the limit of detection is found to be 1.25 nM, which is significantly lower than the permissible limit established by the WHO. Furthermore, possibilities of extending the electrochromism and sensing in the gel state using carbazole derivatives have been explored and the results indicate that low molecular weight carbazole derivatives are promising candidates for electrochromism and sensing applications. [ABSTRACT FROM AUTHOR]

Preparing well-ordered nanotubes on material surface is fundamental for a huge number of applications. Natural surfaces and theoretical approaches show that porous structures such as nanotubes are key parameters for both surface hydrophobicity and water adhesion. Here, a very easy soft-template electropolymerization approach is used to form nanotubes. A solvent of low water-solubility (dichloromethane) is mixed to water in the presence of a surfactant electrolyte for stabilizing the micelles formed in solution. The monomers investigated are thiophene and carbazole derivatives, and are all fully conjugated for favoring the deposition versus polymerization. Indeed, in all the electrodeposited films, the monomer is mostly present as confirmed by cyclic voltammetry. The key parameters in the resulting nanotubes is the monomer structure because a preferential growth is necessary and this one is induced here especially by π-stacking interactions in the direction perpendicular to monomer. The surfaces composed of nanoparticles or nanotubes are the most hydrophobic with an apparent contact angle up to 130.9° accompanied with strong water adhesion, as reported on gecko foot or rose petal. [ABSTRACT FROM AUTHOR]

In the past, considerable effort are focused on advancing blue organic light‐emitting diodes (OLEDs) based on 1,3‐bis(N‐carbazolyl)benzene (mCP). To enhance and stabilize the device performance in vacuum‐processed OLEDs, it is essential to optimize the thermally stable organic materials constituting the emitting layer. The proposed novel carbazole derivative, Ad‐mCP, is designed and synthesized as a host material for blue thermally activated delayed fluorescence OLEDs, which are ideal for vacuum processing. Ad‐mCP exhibits a high glass transition temperature and triplet energy (T1), making it highly compatible with the blue dopant 2,11,14‐tri‐tert‐butyl‐N,N,5‐tris(4‐(tert‐butyl)phenyl)−5H‐5,8b‐diaza‐15b‐borabenzo[a]naphtho[1,2,3‐hi]aceanthrylen‐7‐amine emitter. The incorporation of a rigid adamantane unit into the carbazole group modifies the molecular structure of mCP, preserving crucial photophysical properties, such as T1,while enhancing the morphological and thermal stability of the host material in its film state. Moreover, the spatially hindered molecular structure of Ad‐mCP improves the photoluminescent quantum yield of the emissive layer and enhances charge balance, crucially contributing to the overall efficiency of the OLEDs. As a result, the exceptional performance of Ad‐mCP as a host material for OLEDs resulted in a remarkably high maximum external quantum efficiency of 29.9%, demonstrating superior stability in efficiency even after thermal annealing compared to mCP devices. [ABSTRACT FROM AUTHOR]

G‐quadruplex DNA (GQ‐DNA) represents one of the most significant non‐canonical nucleic acid configurations. GQ‐DNA producing sequences are found in different important genomic areas, including the promoter islands of numerous oncogenes and human telomere regions. Therefore, GQ‐DNA is a key target for anticancer medicines. GQ‐DNA has a highly variable structure, it is critical to develop ligand molecules that selectively target certain quadruplex sequences. Natural products such as pyridocarbazole alkaloids have grown interest for healthcare and medicinal values and they considered as a valuable source of innovative anticancer medicines among the chemical compounds. In this investigation, we have synthesised and characterized pyrido[2,3‐c]carbazole derivative (PCAD) through NMR and IR spectra and explore the interactions between PCAD and Pu24T GQ (promoter region), h‐TELO GQ (telomere region) and duplex DNA by employing several multi‐spectroscopic analytical techniques. We have found that PCAD preferentially interacts with Pu24T GQ DNA as compared to other DNA sequences. These findings highlights PCAD as an appealing option for targeting the Pu24T promoter region and consequently acting as an anti‐cancer drug. This study also highlights the potential for developing drugs to understand the molecular aspects of GQ DNA recognition and signaling, paving the way for future research on GQ biology. [ABSTRACT FROM AUTHOR]

In this study, we used ultraviolet-visible (UV-Vis), fluorescence, and circular dichroism (CD) techniques, as well as molecular modeling, to probe the interactions between carbazole derivatives and the G-quadruplex structure formed in the promoter region of gene Bcl-2. This gene is a rational target for anticancer therapy due to its high expression in a variety of tumors as well as resistance to chemotherapy-induced apoptosis. We employed a sequence with a specific dual G-to-T mutation that may form a mixed-type hybrid G-quadruplex structure in the Bcl-2 P1 promoter region. The three tested carbazole compounds differing in substitution on the nitrogen atom of carbazole interact with the Bcl-2 G-quadruplex by the same binding mode with the very comparable binding affinities in the order of 105 M−1. During absorption and fluorescence measurements, large changes in the ligand spectra were observed at higher G4 concentrations. The spectrophotometric titration results showed a two-step complex formation between the ligands and the G-quadruplex in the form of initial hypochromicity followed by hyperchromicity with a bathochromic shift. The strong fluorescence enhancement of ligands was observed after binding to the DNA. All of the used analytical techniques, as well as molecular modeling, suggested the π–π interaction between carbazole ligands and a guanine tetrad of the Bcl-2 G-quadruplex. Molecular modeling has shown differences in the interaction between each of the ligands and the tested G-quadruplex, which potentially had an impact on the binding strength. [ABSTRACT FROM AUTHOR]

The study of small organic molecules that have different molecular structures with the same luminescent core, which produces fluorescence, phosphorescence or delayed fluorescence, is fascinating. Of course, the regulation of elaborate chemical structures is a reliable way to achieve these emission properties. In this study, five carbazole derivatives with different functional groups were obtained via C–N coupling reactions: Cz–C8, Cz–C8–Br, Cz–C8–OH, Cz–C8–Tu and Cz–C7–COOH. Our results reveal that small differences in functionalized tail groups can produce a huge contrast in photoluminescence behavior. Obviously, more polar tails, such as −Tu and −COOH, contribute more to high-performance organic room temperature phosphorescent materials. The non-polar tail of –H favors delayed fluorescence, while the mid-polar group of –OH enables phosphorescence and delayed fluorescence in Cz–C8–OH. These two different behaviors can be artificially modulated by external stimuli, such as photoactivation and thermal annealing. A study of the internal mechanism shows that intermolecular interactions and the molecular aggregation state are the main factors affecting the photoluminescence performance. Finally, advanced applications in the fields of data encryption, data storage, and anti-counterfeiting are illustrated using time-resolved techniques. [ABSTRACT FROM AUTHOR]

Background: Carbazoles are an important class of heterocyclic aromatic compounds that contain nitrogen atom in the ring. They have a large-conjugated system, attractive "electrical and charge-transport properties", and the ability to efficiently incorporate different functional groups into the structurally inflexible carbazolyl ring. Main text: Carbazole derivative ECCA acts as an anticancer agent by reactivating the P53 molecular signaling pathway; similarly, some other derivatives of carbazole show antifungal activity by acting on the RAS-MAPK pathway. Carbazole derivatives also show their effect on inflammation by inhibiting the p38 mitogen-activated protein kinase signaling pathway by stopping the conversion of DAXX protein into ASK-1. By modifying the AKT molecular signaling pathway through boosting protein phosphatase activity in the brain, they show anti-Alzheimer's activity and also by translocating the GLUT4 these are effective against diabetes. Conclusion: After exploring the literature on carbazole, it was found that carbazole has an immeasurably great potential for the treatment of various diseases as the carbazole nucleus leads to various synthesized derivatives which are used for their pharmacological activities. So there is a need to explore carbazole for some newer drugs. [ABSTRACT FROM AUTHOR]

Surface passivation has been widely employed to suppress non‐radiative charge recombination and prevent interfacial charge accumulation in perovskite photovoltaics. In this report, carbazole modified with ammonium iodide connected via alkyl chains of different lengths (i.e., ethyl, butyl, and hexyl chains) is used to form passivation layers on formamidinium lead triiodide FAPbI3‐based perovskite films to improve operational stability. Owing to the strong hydrophobicity of the carbazole moiety, it is observed that the perovskite films with a carbazole passivation layer retain their initial properties even after direct contact with a water droplet for 100 s. In addition, carbazole treatment reduces the rate of trap‐assisted recombination at the surface and grain boundaries of the perovskite layer. Furthermore, it accelerates interfacial hole transfer from the perovskite to the charge transport layer. As a result, devices treated with carbazole hexylammonium iodide achieve a power conversion efficiency (PCE) of up to 24.3% during quasi‐steady‐state (QSS) measurements with extraordinary long‐term operational stability under conditions of the ISOS‐L‐1 protocol, maintaining 95% of their initial efficiency after 1000 h. [ABSTRACT FROM AUTHOR]

The distinctive electron structures of luminescent radicals offer considerable potential for a diverse array of applications. Up to now, the luminescent properties of radicals have been modulated through the introduction of electron-donating substituents, predominantly derivatives of carbazole and polyaromatic amines with more and more complicated structures and redshifted luminescent spectra. Herein, four kinds of (N-carbazolyl)bis(2,4,6-tirchlorophenyl)-methyl (CzBTM) radicals, Ph2CzBTM, Mes2CzBTM, Ph2PyIDBTM, and Mes2PyIDBTM, were synthesized and characterized by introducing simple phenyl and 2,4,6-trimethylphenyl groups to CzBTM and PyIDBTM. These radicals exhibit rare blueshifted emission spectra compared to their parent radicals. Furthermore, modifications to CzBTM significantly enhanced the photoluminescence quantum yields (PLQYs), with a highest PLQY of 21% for Mes2CzBTM among CzBTM-type radicals. Additionally, the molecular structures, photophysical properties of molecular orbitals, and stability of the four radicals were systematically investigated. This study provides a novel strategy for tuning the luminescent color of radicals to shorter wavelengths and improving thermostability. [ABSTRACT FROM AUTHOR]

Due to side effects and drug resistance, cancer treatment choices are limited despite continued attempts. Topoisomerases are essential for several cellular processes and human topoisomerase I and topoisomerase II alpha inhibitors have proven to be an effective chemotherapeutic alternative for a wide range of cancers, due to its fast proliferating cells and the higher level of these enzymes in solid tumors relative to normal tissue. In this study, around 30 carbazole derivatives were designed using Chem Draw Ultra and their ability to inhibit topoisomerase II was investigated using in silico docking studies and molecular dynamics. The results revealed ligand 10 and ligand 25 held good binding energy scores of -9.21 and -9.50, Kcal mol-1 respectively, with good interaction. ADMET analysis assured the drug likeness and better GI absorption than the parent drug and dexrazoxane. Desmond module of Schrödinger Suite was used and it demonstrated the stability in ligand receptor complexes. [ABSTRACT FROM AUTHOR]

Grain of high yield and quality is needed worldwide due to the needs of a rapidly increasing human population. However, diseases caused by some stubborn types of phytopathogenic bacteria can limit the health and yields of crops. Even worse, conventional commercial bactericides have limited efficacy against such diseases. Therefore, exploring some efficacious bactericidal alternatives is urgently needed. In this work, a new type of 3-(piperazin-1-yl)propan-2-ol modified carbazole derivatives was synthesized and assessed for their bactericidal activity. Among them, compound B16 was the optimal active molecule, giving the EC50 values of 3.11 (Xanthomonas oryzae pv. oryzae), 3.20 (Xanthomonas axonopodis pv. citri) and 3.54 μg/mL (Pseudomonas syringae pv. actinidiae). Pot experiments revealed compound B16 to be able to control rice bacterial leaf blight. Some biochemical assays illustrated that our designed compounds could destroy the integrality of bacterial cell membranes and thereby leading to leaking the intracellular protein. These findings may be regard as a reference for the design of novel membrane-targeting antimicrobial agents for managing stubborn plant bacterial diseases.

Abstract Carbazole derivatives can be used as antioxidants in the lubricating oil industry. The alkylation of carbazole with 2-chloro-2-methylpropane and 2-bromopropane catalyzed by anhydrous aluminum chloride was studied. Initially, 3,6-di-iso-propylcarbazole and 3,6-di-tert-butylcarbazole were using dichloromethane and dibromomethane as solvents at room temperature, respectively. The synthesis conditions were optimized. Subsequently, the effects of reaction time, catalyst dosage, and molar ratio of carbazole to alkylating agent were investigated, and orthogonal experiments were performed. The structures of the carbazole derivatives were characterized by Fourier infrared spectroscopy (FT-IR), mass spectrum (MS) and nuclear magnetic resonance spectroscopy (NMR). The thermal stability of the synthesized carbazole derivatives was investigated by differential scanning calorimetry (DSC). The carbazole derivatives were added into the lubricating oil with a mass fraction of 0.8% and the miscibility, stability and oxidation resistance of the mixed system were evaluated by mechanical stirring and a rotary pressure vessel oxidation test (RPVOT). The DSC results showed that there was good thermal stability for the carbazole derivatives. The mechanical stirring method revealed good solubility and stability for the mixture of oil and carbazole derivatives. The RPVOT results showed that isopropyl carbazole derivatives could increase the oxidation induction period of lubricating oil to 1.39 times, and tert-butyl carbazole derivatives could increase the oxidation induction period of lubricating oil to 1.91 times. The antioxidant effect of tert-butyl carbazole derivatives was better than that of isopropyl carbazole derivatives.

Energy-level alignment is a crucial factor in the performance of thin-film devices, such as organic light-emitting diodes and photovoltaics. One way to adjust these energy levels is through chemical modification of the molecules involved. However, this approach may lead to unintended changes in the optical and/or electrical properties of the compound. An alternative method for energy-level adjustment at the interface is the use of self-assembling monolayers (SAMs). Initially, SAMs with passive spacers were employed, creating a surface dipole moment that altered the work function (WF) of the electrode. However, recent advancements have led to the synthesis of SAM molecules with active spacers. This development necessitates considering not only the modification of the electrode's WF but also the ionization energy (IE) of the molecule itself. To measure both the IE of SAM molecules and their impact on the electrode's WF, a relatively simple method is photo-electric emission spectroscopy. Solar cell performance parameters have a higher correlation coefficient with the ionization energy of SAM molecules with carbazole derivatives as spacers (up to 0.97) than the work function of the modified electrode (up to 0.88). Consequently, SAMs consisting of molecules with active spacers can be viewed as hole transport layers rather than interface layers. [ABSTRACT FROM AUTHOR]

The object of research is newly synthesized carbazole-derived compounds and organic light-emitting structures based on them. The problem lies in the complex solution of scientific and technical problems of improving the characteristics and stability of organic light-emitting diodes (OLEDs), namely improving the brightness and energyefficient parameters. Organic light-emitting structures of blue, blue, and green radiation with color coordinates were formed by the thermovacuum sputtering method and the solution deposition method. The turn-on voltage of the white OLED is 6 V, the maximum brightness of the light-emitting structures was 10,000 cd/m². The devices demonstrated a sufficiently high external quantum efficiency of 5 % to 7 %. This paper reports the multifunctional application of a simple donor-acceptor organic compound, as active and host material in the emission layer of organic light emitting devices. Em1 has been used as active components in OLEDs, where Em1 is the guest emitter (Device A), the acceptor part of the excited emitter (Device B) and the host matrix of the CdSeS/ZnS alloy quantum dot (at least four different OLEDs have been designed and characterized where Em1 plays the role of the guest emitter (Device C). The external quantum efficiencies of devices A–C are characterized by values common to pure fluorescent OLEDs (up to 5 % of the theoretical limit), but these devices sustain low-efficiency roll-off of electroluminescence over a wide range of current densities. Organic light-emitting diodes based on carbazole-derived compounds, due to their color characteristics, are promising candidates for use in the latest lighting systems. A separate advantage of the data light-emitting structures is a multifunctional application of one compound for different types of light-emitting structures. In addition, organic LEDs on based on carbazole-derived compounds have low energy consumption and are environmentally friendly due to the absence of toxic substances in their architecture, which creates prerequisites for saving energy resources and reducing the industrial burden on the environment. [ABSTRACT FROM AUTHOR]

The catalytic conversion of lignin into heterocyclic aromatic compounds holds significant promise not only for expanding lignin's utility in pharmaceutical synthesis but also for imparting luminescent properties to downstream lignin products. However, the challenge lies in devising compatible catalytic conditions for selectively cleaving aromatic ether bonds and forming C–N bonds. In this study, we present a new approach to synthesizing functionalized carbazole derivatives from lignin phenolic β-O-4 model linkages using a one-pot, two-step method. Through a [3 + 1 + 2] benzene cyclization reaction involving lignin β-O-4 model compound, indole-3-carbaldehyde, and 3-chloropropiophenone catalyzed by cost-effective CuCl2·2H2O, we achieved yields of carbazole derivatives up to 90%, highlighting the economic viability of our approach. Our protocol is versatile, accommodating various reaction conditions, including selective cleavage of the C–O bond, aldol condensation, dehydrochlorination of β-chloro ketones, Diels–Alder addition, and dehydroaromatization reactions. Additionally, the resulting carbazole derivatives exhibit favorable twisted-intramolecular charge transfer (TICT) and aggregation-induced emission (AIE) effects. This method offers a sustainable and practical strategy for synthesizing lignin-based carbazoles, with economic advantages in terms of the catalysts and precursors, thereby advancing lignin's application in luminescent materials. [ABSTRACT FROM AUTHOR]

Carbazole derivatives can be used as antioxidants in the lubricating oil industry. The alkylation of carbazole with 2-chloro-2-methylpropane and 2-bromopropane catalyzed by anhydrous aluminum chloride was studied. Initially, 3,6-di-iso-propylcarbazole and 3,6-di-tert-butylcarbazole were using dichloromethane and dibromomethane as solvents at room temperature, respectively. The synthesis conditions were optimized. Subsequently, the effects of reaction time, catalyst dosage, and molar ratio of carbazole to alkylating agent were investigated, and orthogonal experiments were performed. The structures of the carbazole derivatives were characterized by Fourier infrared spectroscopy (FT-IR), mass spectrum (MS) and nuclear magnetic resonance spectroscopy (NMR). The thermal stability of the synthesized carbazole derivatives was investigated by differential scanning calorimetry (DSC). The carbazole derivatives were added into the lubricating oil with a mass fraction of 0.8% and the miscibility, stability and oxidation resistance of the mixed system were evaluated by mechanical stirring and a rotary pressure vessel oxidation test (RPVOT). The DSC results showed that there was good thermal stability for the carbazole derivatives. The mechanical stirring method revealed good solubility and stability for the mixture of oil and carbazole derivatives. The RPVOT results showed that isopropyl carbazole derivatives could increase the oxidation induction period of lubricating oil to 1.39 times, and tert-butyl carbazole derivatives could increase the oxidation induction period of lubricating oil to 1.91 times. The antioxidant effect of tert-butyl carbazole derivatives was better than that of isopropyl carbazole derivatives. [ABSTRACT FROM AUTHOR]

Carbazole derivatives are widely used to make highly efficient optoelectronic materials. In this context, we developed a method for synthesizing conjugated carbazole derivatives using bimetallic Pd–Cu nanoparticles (NPs) immobilized on reduced graphene oxide (rGO) sheets. Pd–Cu NPs were synthesised in a one-pot wet chemical process with ascorbic acid as the reducing agent. The Pd–Cu NPs have an average diameter of 3.8 ± 1.2 nm. X-ray diffraction, SEM, TEM, EDS, and cyclic voltammetry were used to characterise the structure and morphology of the Pd–Cu@rGO NPs. N-Protected-3-aryl/heteroaryl carbazoles were efficiently synthesized using the Pd–Cu@rGO catalyst, which enabled the Suzuki–Miyaura (SM) cross-coupling reaction between N-protected-3-bromo-carbazoles and a range of aryl/heteroaryl boronic acids. The prepared compounds were characterized by NMR (1H & 13C) and HRMS spectra. For the SM reaction, the catalytic performance of the monometallic Pd@rGO and bimetallic Pd–Ni@rGO and Pd–Cu@rGO catalysts were studied with various metal loadings. In comparison to the monometallic Pd@rGO and bimetallic Pd–Ni@rGO catalysts, the bimetallic Pd–Cu@rGO heterogeneous catalyst (L3) demonstrated improved catalytic performance with yields of up to 98%. The material exhibits excellent recyclability and can be reused up to five times without experiencing any decline in its effectiveness. The electronic structure modification offered by the Pd–Cu ensemble on rGO may be responsible for its higher catalytic efficiency. UV and fluorescence spectra were used to investigate the optoelectronic properties of the produced carbazole compounds. Among the compounds studied, 5f, 5n, and 5h exhibited superior UV absorption and fluorescence emission due to the presence of auxochromes and extended conjugation. This study explores the efficacies of the reduced graphene oxide-supported Pd–Cu bimetallic system with different weight% for milder SM reactions. [ABSTRACT FROM AUTHOR]

Carbazole is an aromatic heterocyclic organic compound consisting of two fused benzene rings and a pyrrole ring and is a very valuable building structure for the design of many compounds for use in various fields of chemistry and medicine. This study presents three new carbazole-based thiazole derivatives that differ in the presence of a different halogen atom: chlorine, bromine, and fluorine. Experimental studies and quantum-chemical simulations show the effect of changing a halogen atom on the physicochemical, biological, and linear and nonlinear optical properties. We have also found that carbazoles C-Cl, C-Br, and C-F exhibit high tyrosinase inhibitory activity, with IC50 values in the range of 68–105 µM with mixed mechanism of action. Finally, molecular docking to the active site of Concanavalin A (ConA) and bioavailability for all compounds were evaluated.

Carbazole is a heterocyclic motif that can be found in a diverse array of natural and unnatural products displaying a wide range of biological and physiological properties. Furthermore, this heterocycle is part of electronic materials like photoconducting polymers and organic optoelectronic materials owing to its excellent photophysical characteristics. Consequently, the development of synthetic strategies for carbazole scaffolds holds potential significance in biological and material fields. In this regard, a variety of preparation methods has been developed to exploit their efficient and distinct formation of new C−C and C‐heteroatom bonds under mild conditions and enabling broad substrate diversity and functional group tolerance. Therefore, this review focuses on the synthesis of a set of carbazole derivatives describing a variety of methodologies that involve direct irradiation, photosensitization, photoredox, electrochemical and thermal cyclization reactions. [ABSTRACT FROM AUTHOR]

The persistence and potential toxicity of emergent pollutants pose significant threats to biodiversity and human health, emphasizing the need for sensors capable of detecting these pollutants at extremely low concentrations before treatment. This study focuses on the development of glassy carbon electrodes (GCEs) modified by films of poly-tris(4-(4-(carbazol-9-yl)phenyl)silanol (PTPTCzSiOH), poly-4,4′-Di(carbazol-9-yl)-1,1′-biphenyl (PCBP), and poly-1,3,5-tri(carbazol-9-yl)benzene (PTCB) for the detection of metronidazole (MNZ) in aqueous media. The films were characterized using electrochemical, microscopy, and spectroscopy techniques, including scanning electron microscopy (SEM) and X-ray photoelectron spectroscopy (XPS). Monomers were electropolymerized through cyclic voltammetry and chronoamperometry techniques. Computational methods at the B3LYP/def2-TZVP level were employed to investigate the structural and electrochemical properties of the monomers. The electrochemical detection of MNZ utilized the linear sweep voltammetry technique. Surface characterization through SEM and XPS confirmed the proper electrodeposition of polymer films. Notably, MPN-GCEs exhibited higher detection signals compared to bare GCEs up to 3.6 times in the case of PTPTCzSiOH-GCEs. This theoretical study provides insights into the structural, chemical, and electronic properties of the polymers. The findings suggest that polymer-modified GCEs hold promise as candidates for the development of electrochemical sensors. [ABSTRACT FROM AUTHOR]

A protecting group-dependent diastereoselective synthesis of cyclohepta[b]indole over carbazole derivatives is developed. This strategy involves a regioselective 6-exo-trig radical cyclization-cyclopropanation-ring expansion cascade of 3-propargyl-2-alkenyl indole. The cascade radical cyclization was also performed on indole derivatives possessing alkyne, acrylate and vinylogous carbamate moieties, which delivered pyridocarbazole giving credence to the mechanistic hypothesis. Furthermore, cyclohepta[b]indole could be selectively converted to sulfone and sulfoxide as well as benzoazulenoindole via intramolecular Friedel–Crafts acylation. [ABSTRACT FROM AUTHOR]

The phosphole ring is known as a useful building block for constructing π-conjugated organic materials. Here, we report ladder-type benzophospholo[3,2-b]indole (BPI) derivatives where the phosphole and the pyrrole rings are directly fused. Compounds 8a–8d with different aryl groups on the phosphorous center were successfully synthesized, and the solid-state structure of 8a was confirmed using X-ray crystallographic analysis. The BPIs exhibit relatively high fluorescence quantum yield (Φ 0.50−0.72) and demonstrate a larger Stokes shift compared with a series of benzophospholo[3,2-b]benzoheteroles. The benzophospholo[3,2-b]carbazole derivative 9, which possesses a benzene ring between the phosphole and the pyrrole rings of the BPI, was also synthesized, and its solid-state structure was confirmed using X-ray crystallographic analysis. Compound 9 was found to show a smaller Stokes shift compared with the BPI. [ABSTRACT FROM AUTHOR]

Organic materials showing reversible changes in persistent room‐temperature phosphorescence (RTP) upon exposure to external stimuli have attracted considerable attention in recent years. One potentially groundbreaking development in this area is the introduction of the gating concept for organic persistent RTP materials. This refers to a material where a desired responsive ability only occurs when it is triggered by a specific stimulus, but it remains a formidable challenge. In this study, photoirradiation‐gated excitation‐dependent (Ex‐De) persistent RTP is achieved. A series of molecules, triphenylphosphine and carbazole derivatives connected through flexible carbon chains, are designed and prepared. Upon removal of ultraviolet (UV) irradiation, all these compounds doped polyvinyl alcohol (PVA) films exhibit obvious blue or green afterglow RTP. Among them, (2‐(9H‐[3,9′‐bicarbazol]−9‐yl)ethyl)triphenylphosphonium bromide (TPP‐2C‐Cz) doped PVA film initially exhibits blue persistent RTP after removal of 300 nm excitation but no RTP upon ceasing 365 nm irradiation. Interestingly, upon UV irradiation with a power density of 0.05 W cm−2 (UVA) for 50 min, the Ex‐De RTP behavior of TPP‐2C‐Cz doped PVA film is activated. Eventually, photoirradiation‐gated Ex‐De afterglow emission will be used for a wide range of applications, including the quantitative determination of UV irradiation dose and the permanent record of UV irradiation history, and read on‐demand. [ABSTRACT FROM AUTHOR]

Recently, carbazole-based organic cations have garnered interest for their potential application in two-dimensional (2D) layered hybrid perovskite solar cells because of their strong hole extraction and transport as well as humidity resistance. However, the potential incorporation of carbazole-based Ruddlesden–Popper 2D hybrid perovskites in photodetectors has been largely unexplored. In this study, we synthesized ammonium 1-(9H-carbazol-9-yl) ethanaminium iodide (CzEAI) and fabricated (CzEA)2PbI4 2D perovskite thin films via varying solvent conditions to control film morphology. We constructed photodiode-type photodetectors with the active layer of (CzEA)2PbI4 2D perovskites and demonstrated a specific detectivity of 6.95 × 1010 Jones at 485 nm illumination without external bias. These results demonstrate the potential of carbazole-based 2D perovskites in a wide range of optoelectronic applications. [ABSTRACT FROM AUTHOR]

The cholinesterase inhibitory activity was examined of synthetic carbazole‐coumarin hybrids, with long chain hydrocarbons, triazole, or piperazine as linkers. The most effective acetylcholinesterase inhibitor was 7‐((12‐(9H‐carbazol‐9‐yl)dodecyl)oxy)‐2H‐chromen‐2‐one (3 l), with an IC50 value of 6.86 μM and a high selectivity over butyrylcholinesterase. Compound 3 l also exhibited mixed‐type AChE inhibition in a kinetic study, with a Ki value of 4.87 μM. In addition, molecular docking of compound 3 l toward AChE was done to elucidate the inhibition at both the peripheral anionic and catalytic active sites. Furthermore, the HepG2 and Vero cells were unaffected by toxicity from compound 3 l. Therefore, these findings could be exploited to create a number of carbazole‐coumarin hybrids for future potential treatments for Alzheimer's disease. [ABSTRACT FROM AUTHOR]

A series of new spiro heterocyclic compounds having carbazole and pyrrolidine units were successfully synthesized through a one‐pot, three component, 1,3‐dipolar cycloaddition reaction in good yields with high diastereoselectivity. Simple reaction, easily accessible chemicals, high yield and diastereoselective formation of monospiropyrrolidine and monospiropyrrolizidine carbazole derivatives in one step are some advantages of this method. The structure of the obtained products was characterized by using spectroscopic techniques. [ABSTRACT FROM AUTHOR]

Microporous organic polymers (MOPs) are a new type of porous materials, which have advantages of synthetic diversity, chemical and physical stability, microporous size controllability, etc. MOPs indicate broad applications in various fields such as heterogeneous catalysis, gas adsorption, separation, and storage. In recent years, MOPs have attracted an enormous attention in greenhouse gas capture due to their great potential in physisorptive gas storage. Carbazole and its derivatives have been studied extensively as Metal-Organic Polyhedra (MOPs) building blocks due to their unique structural features and versatile functionalization possibilities. This paper systematically reviews the synthesis, characterization and application of carbazole-based polymers, and relationship of structures and properties of these polymers. The application of the polymers in carbon dioxide (CO2) capture field is analysed taking advantage of their adjustable microporous structure and electron rich properties. This review also provides novel insights regarding functional polymer materials that have high ability of greenhouse gas capture and absorbing selectivity will be obtained by reasonable molecular design and efficient synthesis. [ABSTRACT FROM AUTHOR]

Dopamine D3 receptor (D3R) is implicated in multiple psychotic symptoms. Increasing the D3R selectivity over dopamine D2 receptor (D2R) would facilitate the antipsychotic treatments. Herein, novel carbazole and tetrahydro-carboline derivatives were reported as D3R selective ligands. Through a structure-based virtual screen, ZLG-25 (D3R Ki = 685 nmol/L; D2R Ki > 10,000 nmol/L) was identified as a novel D3R selective bitopic ligand with a carbazole scaffold. Scaffolds hopping led to the discovery of novel D3R-selective analogs with tetrahydro-β-carboline or tetrahydro-γ-carboline core. Further functional studies showed that most derivatives acted as hD3R-selective antagonists. Several lead compounds could dose-dependently inhibit the MK-801-induced hyperactivity. Additional investigation revealed that 23j and 36b could decrease the apomorphine-induced climbing without cataleptic reaction. Furthermore, 36b demonstrated unusual antidepressant-like activity in the forced swimming tests and the tail suspension tests, and alleviated the MK-801-induced disruption of novel object recognition in mice. Additionally, preliminary studies confirmed the favorable PK/PD profiles, no weight gain and limited serum prolactin levels in mice. These results revealed that 36b provided potential opportunities to new antipsychotic drugs with the multiple antipsychotic-like properties.

The all-electron first-principles GW+Bethe–Salpeter method was applied to six carbazole benzonitrile (CzBN) derivatives, which were recently reported to be both thermally activated delayed fluorescence (TADF) active and inactive despite their singlet–triplet splittings being commonly around 0.2 eV. The present method successfully reproduced very similar photoabsorption spectra as experiments from the viewpoint of the peak positions and relative peak heights. We also performed exciton analysis with the exciton wave functions for several lowest singlet and triplet exciton states to reveal the details of the optical properties. We applied this to not only the present six CzBN derivatives but also 18 other TADF molecules and proposed a new exciton map to classify the molecules as the TADF active/inactive by using the exciton binding energy in the vertical axis and the ratio of electron and hole delocalization in the horizontal axis. Our results suggest two possible TADF mechanisms: spatially less localized hole states than the electron states where the exciton binding energy is proportional to the ratio of hole and electron delocalization and spatially more localized hole states than the electron states where the exciton binding energy should be large. [ABSTRACT FROM AUTHOR]

In this study, we used ultraviolet-visible (UV-Vis), fluorescence, and circular dichroism (CD) techniques, as well as molecular modeling, to probe the interactions between carbazole derivatives and the G-quadruplex structure formed in the promoter region of gene Bcl-2. This gene is a rational target for anticancer therapy due to its high expression in a variety of tumors as well as resistance to chemotherapy-induced apoptosis. We employed a sequence with a specific dual G-to-T mutation that may form a mixed-type hybrid G-quadruplex structure in the Bcl-2 P1 promoter region. The three tested carbazole compounds differing in substitution on the nitrogen atom of carbazole interact with the Bcl-2 G-quadruplex by the same binding mode with the very comparable binding affinities in the order of 105 M−1. During absorption and fluorescence measurements, large changes in the ligand spectra were observed at higher G4 concentrations. The spectrophotometric titration results showed a two-step complex formation between the ligands and the G-quadruplex in the form of initial hypochromicity followed by hyperchromicity with a bathochromic shift. The strong fluorescence enhancement of ligands was observed after binding to the DNA. All of the used analytical techniques, as well as molecular modeling, suggested the π–π interaction between carbazole ligands and a guanine tetrad of the Bcl-2 G-quadruplex. Molecular modeling has shown differences in the interaction between each of the ligands and the tested G-quadruplex, which potentially had an impact on the binding strength.

A wide variety of regioselectively substituted carbazole derivatives can be synthesized by the gold‐catalyzed cyclization of alkynols bearing an indol‐3‐yl and an additional group at the homopropargylic positions. The regioselectivity of the process can be controlled by both the oxidation state of the gold catalyst and the electronic nature of the substituents of the alkynol moiety. The 1,2‐alkyl migration in the spiroindoleninium intermediate, generated after indole attack to the activated alkyne, is favored with gold(I) complexes and for electron‐rich aromatic substituents at the homopropargylic position, whereas the 1,2‐alkenyl shift is preferred when using gold(III) salts and for alkyl or non‐electron‐rich aromatic groups. [ABSTRACT FROM AUTHOR]

Parkinson’s disease (PD) is a neurological problem that results mostly in disability globally due to therapeutic challenges. Alpha-synuclein (ASN) and Dopa decarboxylase (DDC) are strongly implicated in the pathogenesis of PD including the aggregation of Lewy bodies and degeneration of dopamine-producing cells. These make them plausible drug targets commonly explored by researchers in the quest for potent inhibitors. However, up to this moment, no inhibitor of ASN has been approved for clinical application while only a handful is available for DDC, as such, searching for effective inhibitors of the dual targets remains essential. In this study, the in-house databases of tetrahydro-β-carboline and carbazole derivatives were virtually screened for putative ligands with multitarget inhibitory mechanisms against the ASN and DDC using molecular docking protocols. Relevant drugs such as phenylbutyrate, anle138b, levodopa, carbidopa and benserazide were used as references. The physicochemical, pharmacokinetics, pharmacodynamics and toxicological profiles of the selected ligands and references were also evaluated in silico using pkCSM. From the virtual screening, ligands 172, 082 and 013 interacted more strongly with ASN receptors with SP glide gscores of –9.154, –9.124 and –8.971 kcal/mol respectively as compared to phenylbutyrate and anle138b with SP glide gscores of –7.181 and –5.875 kcal/mol. They also showed higher binding affinities to DDC receptor by higher SP glide gscores of –6.758, –5.212 and –6.271 kcal/mol than levodopa, carbidopa and benserazide with values of –4.217, –4.502 and –4.18 kcal/mol respectively. Among the 3 ligands, ligand 172 satisfies Lipinski’s Rules of 5 (RO5) and demonstrates ADMET parameters that favor a central nervous system (CNS) drug which was identified as potent inhibitors of ASN and DDC responsible for PD. The potential ligands with stronger inhibitory interactions and good ADMET profile are amenable for further experimental validation in the quest for potent inhibitors of ASN and DDC as anti-PD agents. [ABSTRACT FROM AUTHOR]

Dopamine D 3 receptor (D 3 R) is implicated in multiple psychotic symptoms. Increasing the D 3 R selectivity over dopamine D 2 receptor (D 2 R) would facilitate the antipsychotic treatments. Herein, novel carbazole and tetrahydro-carboline derivatives were reported as D 3 R selective ligands. Through a structure-based virtual screen, ZLG-25 (D 3 R K i = 685 nmol/L; D 2 R K i > 10,000 nmol/L) was identified as a novel D 3 R selective bitopic ligand with a carbazole scaffold. Scaffolds hopping led to the discovery of novel D 3 R-selective analogs with tetrahydro- β -carboline or tetrahydro- γ -carboline core. Further functional studies showed that most derivatives acted as hD 3 R-selective antagonists. Several lead compounds could dose-dependently inhibit the MK-801-induced hyperactivity. Additional investigation revealed that 23j and 36b could decrease the apomorphine-induced climbing without cataleptic reaction. Furthermore, 36b demonstrated unusual antidepressant-like activity in the forced swimming tests and the tail suspension tests, and alleviated the MK-801-induced disruption of novel object recognition in mice. Additionally, preliminary studies confirmed the favorable PK/PD profiles, no weight gain and limited serum prolactin levels in mice. These results revealed that 36b provided potential opportunities to new antipsychotic drugs with the multiple antipsychotic-like properties. Novel carbazole and tetrahydro-carboline derivatives were discovered as D 3 R selective antagonists through the structure-based virtual screen and scaffolds hopping, which were identified with the multiple antipsychotic-like and favorable drug-like properties. [Display omitted] [ABSTRACT FROM AUTHOR]

An efficient and scalable Pd‐catalyzed decarboxylative cross‐coupling strategy for the synthesis of carbazoles has been developed by using N‐aryl anthranilic acids. By employing a well‐designed catalytic system, this protocol access diverse carbazole derivatives via a C−C bond‐formation in one‐pot. The substituted carbazoles were obtained in good to excellent yields with high functional‐group tolerance. We have also demonstrated the gram‐scale synthesis of the anti‐cancer drug Ellipticine by utilizing this methodology. This concise and scalable total synthesis of ellipticine exemplifies the efficiency of our methodology in producing this significant anti‐cancer compound. [ABSTRACT FROM AUTHOR]