Synthesis of multisubstituted quinolines from Baylis–Hillman adducts obtained from substituted 2-chloronicotinaldehydes and their antimicrobial activity

“…Since crystal structures of HDAC3 and HDAC4 in complex with SAHA have not been determined so far, we used the crystal structure of HDAC8 in complex with SAHA which shows sequence similarity (46%) to HDAC4 [1], for docking experiments of compound 5 g , 5 h , and 6 k . We implemented control docking experiments with SAHA to the crystal structure of HDAC8 using AutoDock program [26,27].…”

Section: Molecular Docking Studiesmentioning

confidence: 99%

Design, Synthesis, Molecular Modelling and Biological Evaluation of Novel α-Naphtholhydroxamate Derivatives as Potential Anticancer Agents

Abdelrahim¹,

Mohan²,

Albarrati³

et al. 2016

Med chem (Los Angeles)

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Chemotherapy is one of the treatment options for cancer. A major problem in cancer chemotherapy is the lack of selective toxicity of many commonly used anti-cancer agents towards tumor tissue compared to normal tissue. Studies have shown that α-naphthol is selectively toxic to cultures of human tumor tissue compared to normal tissues in vitro. Hence, this study was conducted to synthesize a series of new hydroxamate derivatives containing α-naphthol nucleus by the reaction of naphthol acetic acid with amino acid methyl ester derivatives which were directly reacted with hydroxyl amine at room temperature. Structures of these compounds were confirmed by standard studies of IR, 1 H NMR, 13 CNMR, MS and elemental analysis. The cytotoxicity of the synthesized compounds were studied using the MTT assay in four human cancer cell lines, including HepG2, PC-3, HT-29 and MCF-7. Among the compounds, compound 6 g and 6 h exhibited a significant cytotoxicity against almost all the used cells including the normal cells . Further studies have shown that the cell death observed was closely associated with generation of reactive oxygen species (ROS). In this study, other naphthol derivatives have shown significant increase in the level of ROS in concentration dependent manner in treated cells. In conclusion, the study has shown that among the synthesized compounds, compounds 6 g , 6 k and 6 h hold the potential for further research. Furthermore, a molecular docking of the tested compounds was carried out to investigate their binding pattern with the prospective target, HDAC (PDB-code: 1T69).

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“…Moreover, this benzofused heteroaromatic ring has been studied and exploited immensely than any other heterocycle for the development of potent pharmacological agents which includes Montelukast (antiasthmatic), Saquinavir (antiviral), Aripiprazole (antipsychotic), etc. Fascinated by multifarious bioactivity of quinoline various researchers and scientists are still engaged in developing potent molecule based on quinoline such as Rao et al [15] have reported the synthesis of multisubstituted quinolines from Baylis-Hillman adduct and tested for antimicrobial activity. Likewise various polyfunctionalized 2-(hetero)arylquinolines were prepared by Kouznetsov et al [16] through imino Diels-Alder reactions and evaluated for antifungal activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and In‐vitro Antimicrobial Activity of Secondary and Tertiary Amines Containing 2‐Chloro‐6‐methylquinoline Moiety

Kumar

Bawa

Kaushik

et al. 2011

Archiv der Pharmazie

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A number of secondary and tertiary amines bearing 2-chloro-6-methylquinoline were synthesized by nucleophilic substitution reaction of 3-(chloromethyl)-2-chloro-6-methylquinoline with substituted aromatic primary and secondary amines in presence of catalytic amount of triethylamine (TEA) and K(2)CO(3). All the compounds were characterized by combined use of IR, (1)H-NMR, (13)C-NMR, mass spectral data, and microanalyses. The newly synthesized quinolinyl amines were screened in vitro for their antifungal activity against Aspergillus niger MTCC 281, Aspergillus flavus MTCC 277, Monascus purpureus MTCC 369, Penicillium citrinum NCIM 768 and for antibacterial activity strains viz. Escherichia coli NCTC 10418, Staphylococcus aureus NCTC 65710, and Pseudomonas aeruginosa NCTC 10662 by agar diffusion technique. Results of the preliminary screening revealed that some of the compounds mainly those with electron withdrawing groups in the phenyl ring showed promising antifungal activity.

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Synthesis of multisubstituted quinolines from Baylis–Hillman adducts obtained from substituted 2-chloronicotinaldehydes and their antimicrobial activity

Cited by 133 publications

References 56 publications

Reactions of Huisgen Zwitterions with Diphenyl Cyclopropenone: A Novel Strategy for the Synthesis of Oxazinone Derivatives

Reactions of Huisgen Zwitterions with Diphenyl Cyclopropenone: A Novel Strategy for the Synthesis of Oxazinone Derivatives

Design, Synthesis, Molecular Modelling and Biological Evaluation of Novel α-Naphtholhydroxamate Derivatives as Potential Anticancer Agents

Synthesis and In‐vitro Antimicrobial Activity of Secondary and Tertiary Amines Containing 2‐Chloro‐6‐methylquinoline Moiety

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