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Molecules 2017, 22(6), 995; doi:10.3390/molecules22060995

Microwave-Assisted Facile Synthesis, Anticancer Evaluation and Docking Study of N-((5-(Substituted methylene amino)-1,3,4-thiadiazol-2-yl)methyl) Benzamide Derivatives

1
Y. B. Chavan College of Pharmacy, Dr. Rafiq Zakaria Campus, Rauza Bagh, Maharashtra, Aurangabad 431001, India
2
Departamento de Química Orgánica, Facultad de Ciencias, Universidad of Santiago De Compostela, Alfonso X el Sabio, Lugo 27002, Spain
3
Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Maharashtra, Aurangabad 431004, India
*
Author to whom correspondence should be addressed.
Academic Editors: Jean Jacques Vanden Eynde and Derek J. McPhee
Received: 18 May 2017 / Revised: 8 June 2017 / Accepted: 12 June 2017 / Published: 15 June 2017
(This article belongs to the Special Issue ECSOC-20)
View Full-Text   |   Download PDF [1273 KB, uploaded 15 June 2017]   |  

Abstract

In the present work, 12 novel Schiff’s bases containing a thiadiazole scaffold and benzamide groups coupled through appropriate pharmacophore were synthesized. These moieties are associated with important biological properties. A facile, solvent-free synthesis of a series of novel 7(al) N-((5-(substituted methylene amino)-1,3,4-thiadiazol-2-yl)methyl) benzamide was carried out under microwave irradiation. Structures of the synthesized compounds were confirmed by IR, NMR, mass spectral study and elemental analysis. All the synthesized hybrids were evaluated for their in vitro anticancer activity against a panel of four human cancer cell lines, viz. SK-MEL-2 (melanoma), HL-60 (leukemia), HeLa (cervical cancer), MCF-7 (breast cancer) and normal breast epithelial cell (MCF-10A) using 3-(4,5-dimethythiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay method. Most of the synthesized compounds exhibited promising anticancer activity, showed comparable GI50 values comparable to that of the standard drug Adriamycin. The compounds 7k, 7l, 7b, and 7a were found to be the most promising anticancer agents in this study. A molecular docking study was performed to predict the probable mechanism of action and computational study of the synthesized compounds 7(al) was performed to predict absorption, distribution, metabolism, excretion and toxicity (ADMET) properties, by using QikProp v3.5 (Schrödinger LLC). The results showed the good oral drug-like behavior of the synthesized compounds 7(al). View Full-Text
Keywords: microwave-assisted synthesis; thiadiazoles; in vitro anticancer activity; molecular docking; ADMET microwave-assisted synthesis; thiadiazoles; in vitro anticancer activity; molecular docking; ADMET
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Tiwari, S.V.; Siddiqui, S.; Seijas, J.A.; Vazquez-Tato, M.P.; Sarkate, A.P.; Lokwani, D.K.; Nikalje, A.P.G. Microwave-Assisted Facile Synthesis, Anticancer Evaluation and Docking Study of N-((5-(Substituted methylene amino)-1,3,4-thiadiazol-2-yl)methyl) Benzamide Derivatives. Molecules 2017, 22, 995.

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