Search

In the present study a library of five (2‐(amino)‐1,3‐thiazin‐6‐one) compounds was synthesized and investigated as against glioblastoma cells in vitro and in vivo in the mice model. The results revealed that all of the five 1,3‐thiazin‐6‐one compounds (4a, 4b, 4c, 4d and 4e) exhibited cytotoxicity against U87MG and 9 L brain cancer cell lines. Moreover, it was found that 9 L cells showed slightly higher sensitivity towards the compounds 4a, 4b, 4c, 4d and 4e compared to U87MG cells. It was observed that the compounds 4a, 4b, 4c, 4d and 4e showed a time‐dependent increase in uptake efficiency by U87MG and 9 L cells. Furthermore, the data revealed that uptake of the compounds and therefore internalization was maximum during initial 1 h of the treatment. Among the synthesized compounds, compound 4c containing trifluoromethyl moiety showed higher uptake efficiency compared to the compound 4a, 4b, 4d and 4e. Treatment of U87MG and 9 L cell tumor spheroids with compound 4c significantly (P<0.05) inhibited the tumor growth compared to the control spheroids. In vivo data revealed that treatment with compound 4c led to a significant (P<0.05) decrease in glioblastoma growth in mice in dose‐dependent manner. Growth of glioblastoma in mice was almost completely inhibited after 28 days of treatment with 2 mg/kg dose of compound 4c. Pharmacokinetic studies showed that compound 4c remained in circulation for longer duration in mice and its terminal half‐life was found to be 6.5 h. Treatment of U87MG and 9 L cells with compound 4c led to a prominent decrease in expression of CYR61 protein. In conclusion, findings of the present study suggest that compound 4c acts as a potential therapeutic agent for the treatment of advanced brain cancer through activation of Hippo pathway. Therefore, more studies need to be performed to investigate the detailed mechanism underlying the inhibitory effect of compound 4c against the glioblastoma. [ABSTRACT FROM AUTHOR]

Targeted radionuclide therapy (TRT) is an effective treatment for tumors. Self-condensation strategies can enhance the retention of radionuclides in tumors and enhance the anti-tumor effect. Considering legumain is overexpressed in multiple types of human cancers, a 131I-labeled radiopharmaceutical ([ 131 I]MAAN) based on the self-condensation reaction between 2-cyanobenzothiazole (CBT) and cysteine (Cys) was developed by us recently for treating legumain-overexpressed tumors. However, liver enrichment limits its application. In this study, a new radiopharmaceutical [ 131 I]IM(HE) 3 AAN was designed and synthesized by introducing a hydrophilic peptide sequence His-Glu-His-Glu-His-Glu ((HE) 3) into [ 131 I]MAAN to optimize the pharmacokinetics. Upon activation by legumain under a reducing environment, hydrophilic [ 131 I]IM(HE) 3 AAN could react with its precursor to form heterologous dimer [ 131 I]H-Dimer that is highly hydrophobic. Cerenkov imaging revealed that [ 131 I]IM(HE) 3 AAN displayed superior tumor selectivity and longer tumor retention time as compared with [ 131 I]MAAN , with a significant reduction in the liver uptake. After an 18-day treatment with [ 131 I]IM(HE) 3 AAN , the tumor proliferation was obviously inhibited, while no obvious injury was observed in the normal organs. These findings suggest that [ 131 I]IM(HE) 3 AAN could serve as a promising drug candidate for treating legumain-overexpressed tumors. [Display omitted] [ABSTRACT FROM AUTHOR]

An approach for the preparation and stabilization of primary phosphine oxides is presented complementing previous methods of in situ generation. Specifically, RP(O)H2 where R=benzyl (Bn), cyclohexyl (Cy), 2‐naphthyl (2‐Naph), phenyl (Ph), tert‐butyl (t‐Bu) was prepared by controlled oxidation of the corresponding primary phosphine in presence of ferrocene as stabilizing reagent. The primary phosphine oxides were characterized using NMR and MS and studied in twofold hydrophosphorylation of diketones. The domino‐phospha‐aldol reaction catalysed with 5 mol% of sodium methoxide yielded five‐, six‐ and seven‐membered heterocyclic tertiary phosphine oxides with a high degree of stereoselectivity, as confirmed by single X‐ray diffraction. [ABSTRACT FROM AUTHOR]

By using amino sulfonic acid salts, formaldehyde, and glyoxal as starting materials, an optimized synthesis process for 2,4,6, 8-tetrachitro-2,4,6, 8-tetraazabicyclic [3.3.0] octane(BCHMX) without purification of the intermediate (2,4, 6,8-tetraazabicyclo[3. 3.0]octane sulfonate) was developed. The molecular structure, crystal structure, and thermal stability of the target product were analyzed and characterized using Fourier transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance spectroscopy (1H NMR), carbon-13 nuclear magnetic resonance spectroscopy (13C NMR), and thermo-gravimetric analysis combined with differential scanning calorimetry (TC-DSC). Results show that, the optimal process conditions are as follows: 1. 07 mole of potassium amino sulfonate per mole of formaldehyde, 1. 77 mole of glyoxal, 8.4 mole of water as the solvent, and 0. 023 mole of formic acid as the acid catalyst. The condensation reaction is carried out for 12 hours. The nitration reaction is performed using fuming nitric acid and acetic anhydride in a molar ratio of 1. 3 ' 1 as nitrating agent at 40°C . By the condensation and nitration reactions, BCHMX with a purity of 97.8% is obtained with a total yield of 65. 29% . BCHMX belongs to the monoclinic crystal system with space group of P2(1)/c, and the theraml decomposition temperature is 223 °C . [ABSTRACT FROM AUTHOR]

Hydrocarboxylation of methyl 2‐octynoate, a chemical commercially available at a low cost, with N‐protected amino acids was developed with a gold‐zinc cooperative catalyst constructed with a 5‐[(2,2′‐bipyridin)‐5‐yl]imidazo[1,5‐a]pyridin‐3‐ylidene to prepare α‐methoxycarbonyl enol esters as acylating reagents. The α‐methoxycarbonyl enol esters were isolable through silica‐gel column chromatography and storable without precautions regarding moisture. Acylation of free amines with the α‐methoxycarbonyl enol esters proceeded without epimerization of the stereogenic center derived from the enol esters, affording analytically pure dipeptide compounds through filtration and hexane‐washing. [ABSTRACT FROM AUTHOR]

A combination of swelling in imidazolium ionic liquids and beta-irradiation – both common pretreatments in biomass processing on their own – leads to unexpected effects, with beta-irradiation causing degradation of the pure ionic liquid and also modification of cellulose suspended in the ionic liquid. The underlying chemistry was investigated in a series of model compound experiments. Here, we report that beta-irradiation of the ionic liquid EMIM-OAc containing equimolar amounts of benzaldehyde and d-glucose affords an unexpected condensation product C17H20O7, of which the structure was elucidated as 5-[(1S,2R,3R)-1,2,3,4-tetrahydroxybutyl]-2-phenyl-3-furoic acid, applying a combination of analytical techniques, mainly NMR spectroscopy, after conversion into the ethyl ester derivative for purification. No reaction at all occurred without beta-irradiation under otherwise identical conditions. Intriguingly, the acetate – the IL´s anion – was incorporated into the condensation product, which can formally be regarded as the condensation product of benzoylacetic acid (from benzaldehyde and the IL´s acetate) and d-glucose. The reaction occurred only when all three components – acetate-type IL, glucose and PhCHO – were irradiated simultaneously. The structure elucidation of the compound is presented, along with a discussion of possible formation mechanisms. Future experiments need to address the generality of the reaction for conversion of other aldehydes and aldoses, and the question of whether a similar process occurs with the reducing end of celluloses or other polysaccharides. [ABSTRACT FROM AUTHOR]

Fabrication of ceramic bodies with complex structures via photopolymerization-based 3D printing with minimal deformation during the inevitable heat treatment necessitates the development of a photopolymerizable ceramic slurry. This study prepared a photocurable slurry using a photocurable resin and particles coated with an inorganic binder. The condensation efficiency of the inorganic binder was improved by applying an aging process to the green bodies, which in turn improved the fracture strength and enhanced the glass conversion efficiency of the particles during the subsequent firing process. The exceptional mechanical properties of the fired bodies fabricated using inorganic binder-coated starting particles can be attributed to the glass matrix formed between the particles rather than the particle-to-particle interfaces. We believe this study demonstrates the feasibility of fabricating ceramic bodies with minimal shrinkage and distortion compared to conventionally sintered bodies. • A photopolymerizable ceramic slurry using inorganic binder-coated particles was developed. • The aging process promoted siloxane bonding and vitrification, which improved the fracture strength. • Excellent mechanical properties are achieved due to the glass matrix formed between the particles. • Shrinkage and distortion are minimized, demonstrating the potential for complex 3D printed ceramics. [ABSTRACT FROM AUTHOR]

Over the last few years, benzimidazole-heterocycle hybrid compounds have received considerable attention due to the wide spectrum of their biological property and many important chemical and pharmacological applications. These compounds have revealed antibacterial, antimicrobial, anticoagulant, antidiabetic and other activities, and they have been used as drugs in the market to treat several diseases. Furthermore, hybrid heterocyclic compounds possessing a benzimidazole skeleton exhibit significant complexing and anticorrosive properties. All of these applications have favored the development of a large number of synthetic strategies to prepare these heterocyclic systems in different reaction conditions. Many research articles on the synthesis of benzimidazole-heterocycle hybrid compounds have been reported in the literature. In this review, we present and discuss the synthetic routes of several benzimidazole-heterocycle hybrid compounds. [ABSTRACT FROM AUTHOR]

Abstract Schiff bases are a diverse group of organic compounds with great pharmaceutical importance due to the presence of carbon–nitrogen double bonds (–C=N–). These compounds are synthesized by the condensation reaction between a primary amine and an aldehyde or ketone in a suitable solvent such as methanol. These compounds have shown antibacterial, antifungal, antiviral, anti-inflammatory, and antioxidant activities, which have garnered the attention of organic chemists in synthesizing these compounds. Recent advances have been summarized in this review paper mainly including compounds with potential antibacterial, antifungal, and antiviral activities. Synthetic schemes are included to provide a better understanding of the Schiff base synthesis mechanism. This review paper will provide a way forward for the pharmaceutical chemist to synthesize new compounds with potential biological activities. Graphical abstract

Ester compounds, widely found in pharmaceutical and natural products, play a crucial role in organic synthesis, prompting the development of numerous methods for their synthesis. An important chemical approach in synthesizing esters from carboxylic acids involves the activation of the carboxyl function, requiring the conversion of the hydroxyl group into a suitable leaving group. This paper presents the findings of our investigations into an efficient method for producing esters from carboxylic acids and alcohols, using the Lewis acid titanium tetrachloride. Titanium tetrachloride has proven highly effective as a coupling reagent for the one-pot formation of esters from carboxylic acids and alcohols operating under mild and neutral conditions. Notably, the reaction eliminates the need for bases, yielding carboxylic esters in high purity and yields. The method is efficient, even with long-chain carboxylic acids, and operates well with primary alcohols in dichloromethane. Steric hindrance, potentially present in carboxylic acids, has a moderate effect on the reaction. Alcohol substrates that easily form stable carbocations require, instead, the use of non-polar solvents like hexane for the reaction. [ABSTRACT FROM AUTHOR]

A convenient and efficient method for the synthesis of benzimidazoles, and benzothiazoles have been developed using recyclable magnetite polydopamine-supported copper nanoparticles (Fe3O4@PDA/CuCl2) under green and mild conditions. This catalytic system enables the one-pot synthesis of benzazoles by employing available, and easy to-handle aldehydes and o-phenylenediamine/o-aminothiophenol. Utilizing sustainable and mild conditions, a variety of functionalized benzazoles has been prepared in nearly quantitative yields (79–97%) within 5–30 min at 40 °C. The method offers advantages such as high yield, short reaction time, use of air as oxidant, ease of workup, avoiding toxic organic solvents, and a simple workup protocol. The catalyst could be recycled and reused up to five times without any loss of significant catalytic activity. The catalyst's great effectiveness can be seen in the fact that the TON reaches 2633–3233 and the TOF reaches 5266–38,800 h−1. [ABSTRACT FROM AUTHOR]

The chemistry of 3-acetylquinoline has attracted increased attention in both synthetic organic and medicinal chemistry. The present review summarizes the published data on the synthesis of 3-acetylquinoline derivatives and their reactions, including reactions involving and not involving the acetyl group. [ABSTRACT FROM AUTHOR]

Copyright of Chemistry & Industry of Forest Products is the property of Chemistry & Industry of Forest Products Editorial Department and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

One of the largest concerns to global health in recent decades has been identified as the growth of bacteria resistance to antibiotics. The Schiff base (SBs) and the zinc(II) SBs complex compounds category have attracted a lot of interest because of their function in chemical syntheses and their potential for bioactive and pharmacological effects. The present study includes the synthesis of various SBs with different substituents. Equimolar mixtures of benzaldehyde derivatives (1, 2) and aniline derivatives (3, 4) are used to carry out a series of condensation reactions to get compounds (5-7). By stoichiometrically combining Zn (II) acetate and ZnCl2 separately with the SBs ligand (7) in ethanol, it has been possible to prepare the SBs zinc(II) complex (8). The structure of the ligand and its metal complex are analyzed using (Fouriertransform infrared spectroscopy, 1H-NMR, 13C-NMR) spectroscopy, scanning electron microscopy, and liquid chromatography–mass spectrometry. Moreover, the synthesized compounds are verified in vitro against Escherichia coli Gram negative, Staphylococcus aureus Gram positive, and fungi (Candida albicans). Compounds (5, 7, and 8) indicated significant growth inhibition against E. coli Gram negative and fungi (C. albicans) with different inhibition zones starting from 7 to 17.5 mm. [ABSTRACT FROM AUTHOR]

The organic compound category known as azomethine oxides has garnered significant attention due to its potential for bioactive and pharmacological effects, as well as its role in organic syntheses. Existing literature offers various methods for producing derivatives of these compounds. This study, in particular, concentrates on the creation of several aromatic oximes through the reduction of corresponding aldehydes. Furthermore, these oximes are employed in the generation of new azomethine oxides through a condensation reaction with selected aldehydes. The molecular structure of the synthesized azomethine oxides is determined using techniques such as Fourier-transform infrared spectroscopy, ¹H-NMR, and 13C-NMR. Finally, the antimicrobial effectiveness of these compounds was assessed against Escherichia coli (gram-negative bacteria), Staphylococcus aureus (gram-positive bacteria), and Candida albicans (fungus). The synthesized compounds were obtained with high purity and yielded excellent results. Furthermore, the data demonstrates that these azomethine oxides exhibit significant antimicrobial activity when compared to standard drugs. [ABSTRACT FROM AUTHOR]

One of the largest concerns to global health in recent decades has been identified as the growth of bacteria resistance to antibiotics. The Schiff base (SBs) and the zinc(II) SBs complex compounds category have attracted a lot of interest because of their function in chemical syntheses and their potential for bioactive and pharmacological effects. The present study includes the synthesis of various SBs with different substituents. Equimolar mixtures of benzaldehyde derivatives (1, 2) and aniline derivatives (3, 4) are used to carry out a series of condensation reactions to get compounds (5-7). By stoichiometrically combining Zn (II) acetate and ZnCl2 separately with the SBs ligand (7) in ethanol, it has been possible to prepare the SBs zinc(II) complex (8). The structure of the ligand and its metal complex are analyzed using (Fourier transform infrared spectroscopy, 1H-NMR, 13C-NMR) spectroscopy, scanning electron microscopy, and liquid chromatography–mass spectrometry. Moreover, the synthesized compounds are verified in vitro against Escherichia coli Gram negative, Staphylococcus aureus Gram positive, and fungi (Candida albicans). Compounds (5, 7, and 8) indicated significant growth inhibition against E. coli Gram negative and fungi (C. albicans) with different inhibition zones starting from 7 to 17.5 mm.

The organic compound category known as azomethine oxides has garnered significant attention due to its potential for bioactive and pharmacological effects, as well as its role in organic syntheses. Existing literature offers various methods for producing derivatives of these compounds. This study, in particular, concentrates on the creation of several aromatic oximes through the reduction of corresponding aldehydes. Furthermore, these oximes are employed in the generation of new azomethine oxides through a condensation reaction with selected aldehydes. The molecular structure of the synthesized azomethine oxides is determined using techniques such as Fourier-transform infrared spectroscopy, 1H-NMR, and 13C-NMR. Finally, the antimicrobial effectiveness of these compounds was assessed against Escherichia coli (gram-negative bacteria), Staphylococcus aureus (gram-positive bacteria), and Candida albicans (fungus). The synthesized compounds were obtained with high purity and yielded excellent results. Furthermore, the data demonstrates that these azomethine oxides exhibit significant antimicrobial activity when compared to standard drugs.

Ester compounds, widely found in pharmaceutical and natural products, play a crucial role in organic synthesis, prompting the development of numerous methods for their synthesis. An important chemical approach in synthesizing esters from carboxylic acids involves the activation of the carboxyl function, requiring the conversion of the hydroxyl group into a suitable leaving group. This paper presents the findings of our investigations into an efficient method for producing esters from carboxylic acids and alcohols, using the Lewis acid titanium tetrachloride. Titanium tetrachloride has proven highly effective as a coupling reagent for the one-pot formation of esters from carboxylic acids and alcohols operating under mild and neutral conditions. Notably, the reaction eliminates the need for bases, yielding carboxylic esters in high purity and yields. The method is efficient, even with long-chain carboxylic acids, and operates well with primary alcohols in dichloromethane. Steric hindrance, potentially present in carboxylic acids, has a moderate effect on the reaction. Alcohol substrates that easily form stable carbocations require, instead, the use of non-polar solvents like hexane for the reaction.

A number of new substances were included into the (5Z)-5-[(2-piperidinequinoline-3-yl)methyl]-2-chloroquinoline structural framework. The condensation process 2-chloroquinoline, which served as a crucial reagent in the reaction with 3-carbaldehydes to produce 2,4-thiazolidinedione, allowed for the production of 1,3-thiazolidine-2,4-dione. The newly developed substances were described by means of their reactions with halide compounds, particularly those pertaining to substituted N-alkylation. Elemental analysis, Fourier-transform infrared spectroscopy (FT-IR), and proton nuclear magnetic resonance spectroscopy ( 1 H NMR) were used to identify the chemical. Furthermore, the antibacterial activity of the produced compounds was evaluated in vitro against a range of pathogens, including Bacillus subtilis, and Escherichia coli. Moreover, docking experiments were conducted using the PDF enzyme of E. coli to improve our understanding of the binding mechanism between the synthesized 5(A-N) compounds and the enzyme., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

Quasi-two-dimensional (Q-2D) perovskites show great potential in the field of photonic and optoelectronic device applications. However, defects and local lattice dislocation still limit performance and stability improvement by nonradiative recombination, unpreferred phase distribution, and unbonded amines. Here, a low-temperature synergistic strategy for both reconstructing and solidifying the perovskite top and buried interface is developed. By post-treating the 1,4-phenylenedimethanammonium (PDMA) based (PDMA)MA 4 Pb 5 I 16 films with cesium acetate (CsAc) before thermal annealing, a condensation reaction between R-COO - and -NH 2 and ion exchange between Cs + and MA + occur. It converts the unbonded amines to amides and passivates uncoordinated Pb 2+ . Meanwhile, it adjusts film composition and improves the phase distribution without changing the out-of-plane grain orientation. Consequently, performance of 18.1% and much-enhanced stability (e.g., stability for photo-oxygen increased over 10 times, light-thermal for T 90 over 4 times, and reverse bias over 3 times) of (PDMA)MA 4 Pb 5 I 16 perovskite solar cells are demonstrated.

Activated carbons have been synthesized by a pyrolytic treatment and a chemical activation with H 3 PO 4 to give rise to amorphous graphite, with high micro-mesoporosity and Brönsted acid sites. These materials have been employed as supports to incorporate Pd species to be used as catalysts in the oxidative condensation of furfural with ethanol to obtain furan-2-acrolein (F2A), as main product. The catalytic results show that F2A is obtained at shorter reaction times, with a maximum yield of 45 % after 180 min at 150 °C. The catalytic studies at longer reaction time worsen the F2A yield due to undesired and uncontrolled condensation reactions, which lead to the formation of humins. On the other hand, it is demonstrated that the amount of oxidant (H 2 O 2) and base (Na 2 CO 3) must be modulated to attain an optimum F2A yield. [Display omitted] [ABSTRACT FROM AUTHOR]