A catalyst- and solvent-free multicomponent synthesis and docking study of some new antiproliferative N 5 -allyl-quinolylpyrido[2,3-b][1,4]benzodiazepinone precursors

A multicomponent reaction has been developed by incorporating quinoline-3-carbaldehyde, 1,3-cyclohexanedione and 2,3-diaminopyridine into some new quinolylpyrido[2,3- b ][1,4]benzodiazepinone assemblies under catalyst- and solvent-free conditions at 120 °C. Further reaction of the resulting intermed...

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Bibliographic Details
Published in:New journal of chemistry 2016, Vol.40 (6), p.4931-4939
Main Authors: Barad, Hitesh A., Sutariya, Tushar R., Brahmbhatt, Gaurangkumar C., Parmar, Narsidas J., Lagunes, Irene, Padrón, José M., Murumkar, Prashant, Sharma, Mayank Kumar, Yadav, Mange Ram
Format: Article
Language:English
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Summary:A multicomponent reaction has been developed by incorporating quinoline-3-carbaldehyde, 1,3-cyclohexanedione and 2,3-diaminopyridine into some new quinolylpyrido[2,3- b ][1,4]benzodiazepinone assemblies under catalyst- and solvent-free conditions at 120 °C. Further reaction of the resulting intermediates with allyl bromide led to the formation of the corresponding N 5 -allylated products, in situ , with higher yields in the same pot. Many candidates of this new class revealed noticeable activities against the representative human solid tumour cell lines A549 (lung), HBL-100 (breast), HeLa (cervix), SW1573 (lung), T-47D (breast) and WiDr (colon). The most active compounds resemble the standard drug etoposide in antiproliferative activity against HeLa, T-47D and WiDr cell lines. Docking studies in the active site of MDM2 led us to consider this protein a plausible target for the antiproliferative effects of the compounds.
ISSN:1144-0546
1369-9261
DOI:10.1039/C5NJ03280F