Synthesis, biological evaluation and 3D QSAR study of 2,4-disubstituted quinolines as anti-tuberculosis agents

Patel, Sanjay R.; Gangwal, Rahul P.; Sangamwar, Abhay T.; Jain, Rahul

doi:10.1016/j.ejmech.2015.02.034

Cited by 26 publications

(9 citation statements)

References 23 publications

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“…The compound 5 has a phenyl substituent at C-4 position of the quinoline ring, suggesting that the presence of this group, directly attached to the nucleus, is fundamental to anti-dermatophytic action when we compare the tested molecules with each other. According to Patel et al [ 52 ], the introduction of a phenyl substituent into the quinoline ring resulted in a good microbiological action. It is possible to suggest that the introduction of a methyl substituent at C-2 position and a phenyl group at C-4 position of the quinoline ring (compound 5) resulted in higher efficiency when compared with other compounds.…”

Section: Resultsmentioning

confidence: 99%

Quinolines derivatives as promising new antifungal candidates for the treatment of candidiasis and dermatophytosis

et al. 2020

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Fungal infections have emerged as a current serious global public health problem. The main problem involving these infections is the expansion of multidrug resistance. Therefore, the prospection of new compounds with efficacy antifungal becomes necessary. Thus, this study evaluated the antifungal profile and toxicological parameters of quinolines derivatives against Candida spp. and dermatophyte strains. As a result, a selective anti-dermatophytic action was demonstrated by compound 5 (geometric means (GM = 19.14 μg ml −1 )). However, compounds 2 (GM = 50 μg ml −1 ) and 3 (GM = 47.19 μg ml −1 ) have presented only anti- Candida action. Compounds 3 and 5 did not present cytotoxic action. Compound 5 did not produce dermal and mucosal toxicity. In addition, this compound showed the absence of genotoxic potential, suggesting safety for topical and systemic use. Quinolines demonstrated a potent anti-dermatophytic and anti-yeast action. Moreover, compound 5 presented an excellent toxicological profile, acting as a strong candidate for the development of a new effective and safe compound against dermatophytosis of difficult treatment. Electronic supplementary material The online version of this article (10.1007/s42770-020-00348-4) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Quinolines derivatives as promising new antifungal candidates for the treatment of candidiasis and dermatophytosis

et al. 2020

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“…The general chemistry for the synthesis of 13 was adapted from the methods reported previously and outlined in Scheme . 13 was acylated to get the ethyl 5‐benzamido‐1 H ‐indole‐2‐ carboxylate ( 14 ) by reacting with benzoyl chloride in toluene at 60 °C for 4 h. 5‐Benzamido‐1 H ‐indole‐ 2‐carbohydrazide ( 15 ) was obtained by dropping hydrazine hydrate in 14 ethanol . The desired analogs ( 3a – 3s , Scheme ) were obtained by dropwise addition of corresponding aldehyde in 15 ethanol solution.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structure–activity relationship studies and biological evaluation of novel 2,5‐disubstituted indole derivatives as anticancer agents

et al. 2016

Chem Biol Drug Des

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Three novel series of 2,5-disubstituted indole derivatives were synthesized and evaluated in vitro for their antiproliferative activity against human cancer cells and HIV-1 inhibition activity used as a readout of cellular activity. Most compounds were found to have potent anticancer activity. In particular, 2c and 3b which showed effectively to repress HIV-1 transcription had a pan antiproliferative activity in cervical cancer cells (HeLa), breast cancer cells (MCF-7), liver cancer cells (HepG2), and lung cancer cells (H460 and A549). While 3b exhibited high sensitivity to A549 cells with the IC value 0.48 ± 0.15 μm, 2c showed high selectivity toward HepG2 cells with the IC value 13.21 ± 0.30 μm. With respect to the cellular mechanism of action, HepG2 cells treated with 2c and A549 cells treated with 3b for 24 h were studied by annexin V/PI staining and Western blot analysis, and results revealed that 2c and 3b may induce cancer cells apoptosis through inhibiting the phosphorylation at Ser2 of RNAPII CTD which can be phosphorylated by cyclin-dependent kinase 9. These studies indicated that 2c and 3b may develop as potent lead compounds in the therapy of cancer. However, determining their roles in preventing HIV-1 still requires further intensive study.

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“…Consequently, at least three interaction areas may be involved in ligand binding, revealing a multiple panorama for the structure-based drug design. On the other hand, thanks to the available number of the recently published PDE4B selective inhibitors, ligand-based Comparative Molecular Fields Analysis (CoMFA) represents a promising alternative tool to investigate the selectivity issue, as already discussed in the literature concerning other case studies [38][39][40][41][42][43][44].…”

Section: Introductionmentioning

confidence: 99%

New insights into PDE4B inhibitor selectivity: CoMFA analyses and molecular docking studies

et al. 2015

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PDE4 inhibitors have been largely studied because of their promising therapeutic effects concerning inflammation and neurodegenerative dysfunctions, such as depression, schizophrenia and Alzheimer's diseases. In this context, the PDE4B isoform proved to be particularly involved in the activation of inflammatory responses, while the PDE4D subfamily is more associated with neuropathologies. The clinical use of PDE4 inhibitors was restricted by the presence of prominent side effects probably due to their non-specific action across the different isoforms. Therefore, this work deals with the development of 3D-QSAR models, supported by molecular docking studies, to identify the key requirements underlying selective PDE4B or PDE4D inhibition. The results highlighted the ligand-based approach as a promising tool to guide the rational design of novel PDE4 inhibitors endowed with high affinity and selectivity profiles. The alignment of compound 1-85 and the model A statistical results are depicted.

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Synthesis, biological evaluation and 3D QSAR study of 2,4-disubstituted quinolines as anti-tuberculosis agents

Cited by 26 publications

References 23 publications

Quinolines derivatives as promising new antifungal candidates for the treatment of candidiasis and dermatophytosis

Quinolines derivatives as promising new antifungal candidates for the treatment of candidiasis and dermatophytosis

Synthesis, structure–activity relationship studies and biological evaluation of novel 2,5‐disubstituted indole derivatives as anticancer agents

New insights into PDE4B inhibitor selectivity: CoMFA analyses and molecular docking studies

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