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( Z/E )-3-(1,8-Dichloro-9,10-dihydro-9,10-ethanoanthracen-11-yl)acrylaldehyde 2 has been investigated experimentally and theoretically. The Wittig reaction of 1,8-dichloro-9,10-dihydro-9,10-ethanoanthracene-11-carbaldehyde 1 and (triphenylphosphoranylidene) acetaldehyde in toluene under reflux conditions resulted in compound 2 . Spectroscopic characterization of compound 2 was performed by the Fourier-transform infrared spectroscopy, nuclear magnetic resonance, and high-resolution mass spectroscopy techniques. Density functional theory (DFT) calculations were conducted to study various global and local reactive properties. The spectra were also obtained by DFT calculations and corresponding comparisons were performed to validate the level of theory. Using DFT calculations, reactivity has been studied based on frontier molecular orbitals, charge distribution, average local ionization energies, Fukui functions, and bond dissociation energies for hydrogen abstraction. Molecular dynamics simulations have been used to investigate the influence of water as a solvent for compound 2 . Finally, compound 2 was docked into the central and allosteric binding sites of the serotonin transporter enzyme and was found to be a good candidate as an antidepressant-like compound. [ABSTRACT FROM AUTHOR]

The microwave-assisted three-component reactions of 3,5-bis(E)-arylmethylidene] tetrahydro-4(1H)-pyridinones, acenaphthenequinone and cyclic α-amino acids in an ionic liquid, 1-butyl-3-methylimidazolium bromide, occurred through a domino sequence affording structurally intriguing diazaheptacyclic cage-like compounds in excellent yields. [ABSTRACT FROM AUTHOR]

• Synthesis of a structurally unexplored novel class of ferrocene fused spiropyrrolidine hybrid. • Spiro compound was achieved in excellent yield via a one-pot multicomponent cascade protocol. • The synthesized compound was elucidated by spectroscopic, X-ray diffraction and computational studies. • Spirocompound displayed significant activity against tested MDR S. aureus strains. Our synthetic approach for the assembly of highly diversified spiropyrrolidine grafted ferrocene was based on a one-pot four component cascade reaction protocol involving 1,3-dipolar cycloaddition reaction of (E)-3-ferrocene-1-(4-bromophenyl)prop‑2-en-1-one and azomethine ylide generated in situ from quinoxalinone and l -tryptophan. The structure of the compound was assigned by one- and two-dimensional NMR spectroscopic studies. The regio- and stereochemistry of the spirocompound was confirmed by single crystal X-ray diffraction analysis. The nature of three-dimensional orientation of the synthesized compound has been investigated through single crystal X-ray diffraction study. Crystal structure of the synthesized compound was analyzed using Hirshfeld calculations. In spirocompound, the packing of molecules is controlled by significant O...H (3.3%), N...H (4.1%) and C H...π (24.8%) interactions. The different π-donation and π-back donation interactions was analysed using NBO calculations. The compound 6 exhibited potent inhibitory activity against tested MDR S. aureus strains ranging from 8.00 to 256.00 µg/mL with respect to MIC and MBC determination. [ABSTRACT FROM AUTHOR]

Highlights: [•] Synthesis of hitherto unreported morpholine fused unusual spiroheterocyle. [•] Product achieved in good yield via one-pot cascade reaction sequence. [•] The structure determined by spectral and single crystal X-ray diffraction studies. [•] Formation of spiroheterocyle has been investigated through DFT calculation. [ABSTRACT FROM AUTHOR]

[Display omitted] • Novel spirooxindolopyrrolidine tethered indandiones have been synthesized in excellent yields. • A one-pot eco-friendly three component cycloaddition strategy have been employed. • Compounds were assessed for their antimycobacterium activity against Mtb H37Rv. • Compound with chloro substituent displayed two fold activity than that of standard drug, ethambutol. Novel spirooxindolopyrrolidine embedded indandione heterocyclic hybrids were obtained in excellent yields via a regio- and stereoselective one-pot three component reaction between Baylis-Hillman adduct and non-stabilized azomethine ylides. The structure of newly synthesized compounds was elucidated through 1D and 2D spectroscopic data and the stereochemistry was determined by single crystal X-ray diffraction analysis. In vitro tubercular activity against Mycobacterium tuberculosis H37Rv using MABA assay reveals that the compound bearing chlorine substituted on the oxindole ring displayed the most potent activity with MIC 0.78 μg/mL and is two-fold active than the standard drug, ethambutol (MIC 1.56 μg/mL). [ABSTRACT FROM AUTHOR]

• Structurally intriguing novel spiroheterocyclic hybrid has been synthesized in excellent yield. • Spiroheterocycle has been achieved via one-pot [bmim]Br accelerated multicomponent green protocol. • The structure and stereochemistry of the compound elucidated by spectroscopic and X-ray analysis. • Molecular packing and interaction has been investigated by Hirshfeld and DFT calculations. • Food borne bacterial inhibitory activity observed. Synthesis of a hybrid heterocycle comprising ferrocene, spiropyrrolidine and quinoxaline structural moieties have been achieved in good yield via ionic liquid expedited multicomponent 1,3-dipolar cycloaddition reaction. Structural properties of the synthesized compound were exploited using single crystal X-ray crystallographic studies. Hirshfeld analysis revealed the importance of H...H (59.6%), C H...π (22.4%) and N...H (3.5%) contacts within the molecular packing. The Fe-C interactions around ferrocenyl moiety were investigated using Natural Bond Orbital (NBO) and Atoms In Molecules (AIM) calculations. A predominant covalent character of interactions between Fe-C were been accessed from AIM calculation. A weaker extend of π-back donation appeared in cyclopentadienyl moiety carrying the substituent instead of unsubstituted one. Further, the in vitro antimicrobial potential of the synthesized compound against five food borne bacterial pathogens reveals its significant activity against E. coli and S. enterica with MIC values 6.00 µg/mL and 8.00 µg/mL, respectively. The antioxidant activity of compound 5 was found to be 84.37±0.55 at 250 µg/mL concentration with an IC 50 value = 33.80 µg/mL. [ABSTRACT FROM AUTHOR]

A stereo‐, regio‐ and chemoselective synthesis of a series of structurally diverse novel oxobenzothiophene embedded spirooxindolopyrrolidine/pyrrolizidine hybrid heterocycles were achieved in excellent yields by multicomponent 1,3‐dipolar cycloaddition reaction process. The 1,3‐dipole component employed was generated in situ from isatin and N‐methylglycine/L‐proline while the dipolarophile, ethyl 2‐(3‐oxobenzo[b]thiophen‐2(3H)‐ylidene)acetate was prepared from thiophenol in two good yielding steps. The formation of spiroheterocyclic hybrids occurred through the formation of two C=C and one C−N bonds in a single synthetic transformation. The compounds formed consists of three adjacent stereocenters, out of which two are spirocarbons. The synthesized spiro compounds were assayed for their AChE/BChE inhibitory activity and most of the spirocompounds showed promising cholinesterase inhibitory activity. Among them, spiropyrrolidine that substituted with chlorine atom on the oxindole ring displayed significant activity (4.16±0.09 μM) with respect to standard drug, galantamine (2.09±0.11 μM). Molecular modelling simulation was explored for the most potent compound that revealed interesting binding templates to the active site of enzyme. [ABSTRACT FROM AUTHOR]

An abstract of the article "Straightforward Synthesis of Pyrrolo[3,4-b]quinolines Through Intramolecular Povarov Reactions" by Abdulrahman I. Almansour, Natarajan Arumugam and colleagues is presented.

Bifunctional polycyclic cage structures are synthesized in an ionic liquid by a sustainable microwave-assisted three-component [3+2] cycloaddition-annulation of diarylidene-4-piperidinones, acenaphthenequinone, and amino acids in good to excellent yields with complete regio- and stereoselectivity. [ABSTRACT FROM AUTHOR]

The synthesis of the tetracyclic compounds 1-(4,5-dichloro-9,10-dihydro-9,10-ethanoanthracen-11-yl)-N-methylmethanamine (5) and 1-(1,8-dichloro-9,10-dihydro-9,10-ethanoanthracen-11-yl)-N-methylmethanamine (6) as a homologue of the anxiolytic and antidepressant drugs benzoctamine and maprotiline were described. The key intermediate aldehydes (3) and (4) were successfully synthesized via a [4 + 2] cycloaddition between acrolein and 1,8-dichloroanthracene. The synthesized compounds were investigated for antidepressant activity using the forced swimming test. Compounds (5), (6) and (3) showed significant reduction in the mice immobility indicating significant antidepressant effects. These compounds significantly reduced the immobility times at a dose 80 mg/kg by 84.0%, 86.7% and 71.1% respectively. [ABSTRACT FROM AUTHOR]

A library of novel trans-ethyl 5-aroyl-4-aryl-2-[(arylsulfonyl)methyl]-4,5-dihydrofuran-3- carboxylates were synthesized regio- and stereoselectively in good yields by a three-component domino reaction of ethyl-3-oxo-4-(arylsulfonyl)butanoates, aromatic aldehydes and Nphenacylpyridinium bromide in presence of triethylamine in acetonitrile under heating. This transformation generates C-O, C-C and C=C bonds and presumably proceeds via an α,β- unsaturated ketosulfonyl ester generation/Michael addition/intramolecular cyclisation domino sequence. [ABSTRACT FROM AUTHOR]

Abstract: A facile and efficient synthesis of novel chromeno[4,3-b]pyrroles has been accomplished by intramolecular 1,3-dipolar cycloaddition which on subsequent Pictet–Spengler cyclisation in presence of p-toluenesulfonic acid yielded indolizino[6,7-b]indoles. The synthesized chromenopyrroles and indolizinoindoles were evaluated for their antimicrobial and antioxidant activities. Compounds 7b, 7e, 7a and 7d exhibited respectively, good antibacterial and antifungal activities against tested pathogens when compared to reference control. [Copyright &y& Elsevier]

With an aim to develop more effective and affordable anticancer agents possessing a unique mechanism of action, we designed and synthesized derivatives of spirooxindole-pyrrolidine heterocyclic hybrids in good yields through a one-pot three-component (3+2) cycloaddition strategy. The synthesized compounds were characterized thoroughly for the physicochemical properties by making use of FT-IR, NMR spectroscopy, and mass spectrometry. Further, these compounds have been evaluated for the influence of anticancer activity against HepG2 cells up to 200 µg/mL concentration. The highly active molecular scaffold was tested for the in-depth mechanistic studies, and it was found that the major pathway of cell death is apoptosis which occurs through the induction of reactive oxygen species followed by the involvement of caspases. [ABSTRACT FROM AUTHOR]

• Dispiropyrrolidines synthesized in excellent yield via cycloaddition strategy. • Compounds were elucidated by spectroscopic and single crystal X-ray analysis. • Molecular packing and structure reactivity descriptors were investigated. • Compounds assayed for their antimicrobial activity against K. pneumonia strains. • Antimicrobial efficacy was also performed through molecular docking study. A regio and stereoselective synthesis of a new class of spirooxindolopyrrolidine embedded indandione heterocycles was obtained in excellent yield employing a three-component cascade reaction protocol. The key step for this protocol is a 1,3-dipolar cycloaddition reaction involving azomethine ylide generated in situ from isatin and l -phenylalanine. The structure of newly synthesized compound was assigned based on the NMR spectroscopic analysis and the stereo/regiochemistry was undoubtable assigned by single crystal X-ray diffraction analysis. Further, the structural determination of the compound was assigned through density functional theory (DFT) and Hirshfeld surface analysis. It is found that the compound was highly stabilized by intermolecular interactions such as X-H-H-X (X = C and O) and also by hydrogen bonding interaction. The synthesized compounds were assayed for their antibacterial activity against five different clinical bacterial strains of K. pneumoniae and found that the compound possessing chloro‑substitution on aryl ring showed significant activity against tested K. pneumoniae strains. [Display omitted] [ABSTRACT FROM AUTHOR]

A facile one-pot domino reaction for the stereoselective synthesis of acryl derivatives has been reported using alkaline earth catalyst [Ca(OTf) 2 ]. Initially aryl amine reacts with ethyl propiolate to form β-enamino ester which further reacts with aryl aldehyde and indole in the presence of Ca(OTf) 2 to give indolyl acrylates. It is interesting to note that in the absence of indole the reaction leads to the formation of benzylidene bisacrylates. Similarly β-enamino ester reacts with another electrophilic partner isatin in the presence of Ca(OTf) 2 to give oxindolyl acrylates. The products were isolated in good yields by simple filtration. [ABSTRACT FROM AUTHOR]

• Synthesis of structurally intriguing fused pyrroloquinoline hybrid heterocycle in excellent yield. • Compound was achieved via one-pot cascade protocol under eco-friendly solvent free condition. • Compound was assigned by spectroscopic and single crystal X-ray diffraction analysis. • Molecular packing and structure reactivity descriptors were investigated via computational studies. • Compound showed significant antimicrobial activity against tested bacterial and fungal pathogens. Synthesis of a structurally complex hitherto unexplored novel class of pyrene fused pyrroloquinolinone was achieved in excellent yield via an environmental friendly solid-state melt reaction condition employing multicomponent cascade protocol which involves 1,3-dipolar cycloaddition and subsequent double annulation process. The 1,3-dipole component was derived in situ from diketone and α-amino acid, whereas the Baylis-Hillman adduct synthesized from pyrene-1-carbaldehyde was utilized as a dipolarophile. Structure of the compound was elucidated by 1H and 13C NMR spectroscopic analysis and further confirmed through single crystal X-ray diffraction and the molecular packing was described by using Hirshfeld surface analysis. The structure-reactivity descriptors of the synthesized compound were examined through DFT calculations. The pyrroloquinoline was evaluated for its antibacterial activity against three multi drug resistant bacterial and two fungal pathogens. The MIC value of the tested microbial pathogens were exhibited with minimum (0.156 mg/mL) and maximum (1.250 mg/mL). The antimicrobial results disclosed that compound 6 is considered as a potent candidate for effective therapeutic applications. [ABSTRACT FROM AUTHOR]

An abstract of the article "Synthesis of Highly Functionalized 2-Thiaspiro[4.5]deca-6,8-dienes via Atom Efficient Tandem Michael Addition/Thorpe-Ziegler Cyclization" by Mani Anusha Rani and colleagues is presented.

Review: [129 refs. [ABSTRACT FROM AUTHOR]