Title: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
VOLUME: 18 ISSUE: 5
Author(s):Pravin S. Bhale, Hemant V. Chavan*, Sakharam B. Dongare, Sagar T. Sankpal and Babasaheb P. Bandgar*
Affiliation:School of Chemical Sciences, Solapur University, Solapur-413 255, Maharashtra, School of Chemical Sciences, Solapur University, Solapur-413 255, Maharashtra, School of Chemical Sciences, Solapur University, Solapur-413 255, Maharashtra, Department of Chemistry, A.S.P. College, Devrukh, Dist-Ratnagiri-415 804, Maharashtra, School of Chemical Sciences, Solapur University, Solapur-413 255, Maharashtra
Keywords:α-Aroylketene dithioacetal, 2-aminobenzothiazole, cytotoxicity, anti-inflammatory, antioxidant, α-amylase inhibition.
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.
