Synthesis, characterization and anticancer activity of certain 3-{4-(5-mercapto-1,3,4-oxadiazole-2-yl)phenylimino}indolin-2-one derivatives

doi:10.1016/j.jsps.2011.03.002

PMID: 23960753DOI: 10.1016/j.jsps.2011.03.002Jul 1, 2011

Synthesis, characterization and anticancer activity of certain 3-{4-(5-mercapto-1,3,4-oxadiazole-2-yl)phenylimino}indolin-2-one derivatives

Saudi Pharmaceutical Journal : SPJ : the Official Publication of the Saudi Pharmaceutical Society

Rajyalakshmi GudipatiSarangapani Manda

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Abstract

A series of 5- or 7-substituted 3-{4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenylimino}-indolin-2-one derivatives were synthesized by treating 5-(4-aminophenyl)-1,3,4-oxadiazole-2-thiol with different isatin derivatives. The newly synthesized compounds were characterized on the basis of spectral (FT-IR, (1)H NMR, MS) analyses. All the synthesized derivatives were screened for anticancer activity against HeLa cancer cell lines using MTT assay. All the synthetic compounds produced a dose dependant inhibition of growth of the cells. The IC50 values of all the synthetic test compounds were found between 10.64 and 33.62 μM. The potency (IC50 values) of anticancer activity of compounds VIb-d was comparable with that of known anticancer agent, Cisplatin. Among the synthesized 2-indolinones, compounds VIb-d with halogen atom (electron withdrawing groups) at C5 position showed the most potent activity. These results indicate that C5 substituted derivatives may be useful leads for anticancer drug development in the future.

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Synthesis, characterization and anticancer activity of certain 3-{4-(5-mercapto-1,3,4-oxadiazole-2-yl)phenylimino}indolin-2-one derivatives

Abstract

References

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New colorimetric cytotoxicity assay for anticancer-drug screening

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The endogenous oxindoles 5-hydroxyoxindole and isatin are antiproliferative and proapoptotic

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Synthesis and pharmacological activities of hydrazones, Schiff and Mannich bases of isatin derivatives

Genotoxicity of two anticancer drugs, gemcitabine and topotecan, in mouse bone marrow in vivo

Synthesis and primary cytotoxicity evaluation of 3-[[(3-phenyl-4(3H)-quinazolinone-2-yl)mercaptoacetyl]hydrazono]-1H-2-indolinones

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Design, synthesis and evaluation of antiinflammatory, analgesic and ulcerogenicity studies of novel S-substituted phenacyl-1,3,4-oxadiazole-2-thiol and Schiff bases of diclofenac acid as nonulcerogenic derivatives

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Novel 1-(4-substituted benzylidene)-4-(1-(substituted methyl)-2,3-dioxoindolin-5-yl)semicarbazide derivatives for use against Mycobacterium tuberculosis H37Rv (ATCC 27294) and MDR-TB strain

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Synthesis and biological evaluation of new naphthalene substituted thiosemicarbazone derivatives as potent antifungal and anticancer agents

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Design, synthesis and antiepileptic properties of novel 1-(substituted benzylidene)-3-(1-(morpholino/piperidino methyl)-2,3-dioxoindolin-5-yl)urea derivatives

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(13)C NMR substituent-induced chemical shifts in 4-(substituted phenyl)-3-phenyl-1,2,4-oxadiazol-5(4H)-ones (thiones)

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1,3,4-oxadiazole and its derivatives: A review on recent progress in anticancer activities.

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Synthesis and biological evaluation of newer 1,3,4-oxadiazoles incorporated with benzothiazepine and benzodiazepine moieties.

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