Department of Chemistry

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Subject: search.filters.subject.Anticancer activity

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    Synthesis of novel multifunctional spirobibenzopyran derivatives: Crystal structure, In-silico study, anticancer activity and antimycobacterial activity
    (Elsevier, 2025) Shukla, Paritosh
    A Novel series of multifunctional Spirobibenzopyran derivatives were synthesized from derivatives of 2-hydroxybenzaldehyde and various ketones with α-hydrogen. Single crystal X-ray analysis was obtained for three compounds. The drug-likeliness and toxicity predictions confirmed minimal toxicity (class IV). Docking showed good complementarity of active compounds with the colchicine binding site of tubulin. Molecular docking showed that methoxy group containing compound-7 binds to the proposed target (colchicine active site) with highest docking score. The synthesized molecules were evaluated as potent anticancer agents against MCF-7, MDA-MB-231 (human breast carcinoma) and A549 (human lung carcinoma) cell lines using MTT assay. In general, substituted spirobibenzopyran compounds showed higher activity towards the lung cancer cell line (A549) and breast cancer cell line (MCF-7 and MDA-MB-231) as compared to unsubstituted spirobibenzopyran molecule. They exhibit competitive results with the reference drug Crizotinib and 5-Fluorouracil. Spirobibenzopyran compound-5 with two phenolic hydroxyl group revealed a promising drug profile, inhibiting cell growth and proliferation against lung cancer cell line (A549) with IC50 value 13.54 ± 3.46 µM. Methoxy substituted compound-7 showed best potency among all spirobibenzopyrans against triple negative cell line MDA-MB-231 having IC50 value 18.96 ± 5.77 µM. As per our best knowledge this is the first report of Antimycobacterial activity of spirobibenzopyrans against Mycobacterium smegmatis MC2 155. Compound-6 with polar carboxylic acid functionality showed enhanced Antimycobacterial activity (MIC 5 µg/mL) as compared to standard drug Rifampicin.
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    Scaffold-Hopping Strategy: Synthesis and Biological Evaluation of 5,6-Fused Bicyclic Heteroaromatics To Identify Orally Bioavailable Anticancer Agents
    (ACS, 2011-03-24) Shukla, Paritosh
    Utilizing a scaffold-hopping drug-design strategy, we sought to identify a backup drug candidate for BPR0L075 (1), an indole-based anticancer agent. For this purpose, 5,6-fused bicyclic heteroaromatic scaffolds were designed and synthesized through shuffling of the nitrogen from the N-1 position or by insertion of one or two nitrogen atoms into the indole core of 1. Among these, 7-azaindole core 12 showed potent in vitro anticancer activity and improved oral bioavailability (F = 35%) compared with 1 (F < 10%).
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    An expeditious synthesis and anticancer activity of novel 4-(3′-indolyl)oxazoles
    (Elsiever, 2010-03) Kumar, Dalip
    A series of 4-(3′-indolyl)oxazole congeners have been synthesized and studied for their cytotoxicity against six cancer cell lines. Reaction of 3-acetyl-1′-benzenesulfonylindole with [hydroxy(tosyloxy)iodo]benzene afforded pure 3-tosyloxyacetyl-1′-benzenesulfonylindole. Microwave-accelerated neat reaction of 3-tosyloxyacetyl-1-benzenesulfonylindole with amides resulted in the exclusive formation of 4-(1′-benzenesulfonylindol-3′-yl)-2-substituted oxazoles (4) in very good yield. Treatment of 4 with aqueous sodium hydroxide under refluxing conditions afforded pure 4-(3′-indolyl)-2-substituted oxazoles (5) in excellent yield. The 4-(3′-indolyl)oxazoles 5d and 11 were found to be most cytotoxic and selective against various cancer cell lines. Compounds 5g, 5j and 5l showed moderate anticancer activity.
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    Synthesis of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates and evaluation of their Src kinase inhibitory and anticancer activities
    (Elsiever, 2011-03) Kumar, Anil
    A series of two classes of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates were synthesized using click chemistry approach. All compounds were evaluated for inhibition of Src kinase and human ovarian adenocarcinoma (SK-Ov-3), breast carcinoma (MDA-MB-361), and colon adenocarcinoma (HT-29). Hexyl triazolyl-substituted 3-phenylpyrazolopyrimidine exhibited inhibition of Src kinase with an IC50 value of 5.6 μM. 4-Methoxyphenyl triazolyl-substituted 3-phenylpyrazolopyrimidine inhibited the cell proliferation of HT-29 and SK-Ov-3 by 73% and 58%, respectively, at a concentration of 50 μM.