α-Aroylketene Dithioacetal Mediated Synthesis of (E)-3-(benzo[d]thiazol-2-ylamino)-2-(1-methyl-1H-indole-3-carbonyl)-3-(methylthio)acrylonitrile Derivatives and their Biological Evaluation

Author(s): Pravin S. Bhale , Hemant V. Chavan* , Sakharam B. Dongare , Sagar T. Sankpal , Babasaheb P. Bandgar* .

Journal Name: Anti-Cancer Agents in Medicinal Chemistry

Volume 18 , Issue 5 , 2018

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Abstract:

Background: The blending of two pharmacophores would generate novel molecular templates that are likely to exhibit interesting biological properties.

Objective: A facile, efficient and high yielding synthesis of (E)-3-(benzo[d]thiazol-2-ylamino)-2-(1-methyl-1Hindole- 3-carbonyl)-3-(methylthio) acrylonitrile derivatives and evaluation of therapeutic potential.

Method: The synthesis of target molecules has been achieved by reacting 2-aminobenzothiazole and substituted 2-(1-methyl-1H-indole-3-carbonyl)-3,3-bis(methylthio)acrylonitrile in the presence of a catalytic amount of sodium hydride in THF. Structural investigations were carried using 1H NMR, 13C NMR, FT-IR, and HRMS data.

Results: In vitro anti-tumor evaluation of the synthesized compounds against MCF-7 (breast carcinoma) cell line revealed that they possess good anti-tumor activities. Compounds, 4j and 4i demonstrated significant activities against breast carcinoma (GI50 14.3 and 19.5 µM respectively). Most of the synthesized compounds were also found to be excellent NO, H2O2, DPPH, and superoxide radical scavengers. Anti-diabetic and antiinflammatory evaluation also displayed moderate activity.

Conclusion: Among the compounds synthesized some of the compounds possess significant anticancer, antioxidant and anti-inflammatory properties.

Keywords: α-Aroylketene dithioacetal, 2-aminobenzothiazole, cytotoxicity, anti-inflammatory, antioxidant, α-amylase inhibition.

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Article Details

VOLUME: 18
ISSUE: 5
Year: 2018
Page: [757 - 764]
Pages: 8
DOI: 10.2174/1871520617666170912124258
Price: $58

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