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■ Synthesis, Molecular Docking and Anti-Human Breast Cancer Activities of Novel Thiazolylacetonitriles and Thiazolylacrylonitriles and Their Derivatives Containing Benzenesulfonylpyrrolidine Moiety

Mahmoud S. Bashandy* and Shimaa M. Abd El-Gilil

*Department of Chemistry, Al-Azhar University, Nasr City, Cairo 002, Egypt

Abstract

This article describes the synthesis of some novel sulfonamides having the biologically active, thiazole 3, 8-10, 13, 19, 20, 24, 30, 31, 35-41, pyrazolo[5,1-c][1,2,4]triazine 5, 1H-1,2,4-triazole 6, thiazolo[3,2-a]pyridine 14, chromen-2-one 16, benzo[f]chromen-3-imine 17, benzo[f]chromen-3-one 18, triazolo[4,3-a]pyrimidine 22, pyrazolo[1,5-a]pyrimidine 23, isoxazole 26, 2,4-diaminopyrimidine 27, benzo[4,5]imidazo[1,2-a]pyridine 28, imidazolidine 32 and 1H-benzo[d]imidazolidene 33 moieties, starting with 2-(4-(4-(pyrrolidin-1-ylsulfonyl)phenyl)thiazol-2-yl)acetonitrile (2), which was prepared from cyclocondensation of phenacyl bromide derivative 1 with 2-cyanoethanethio-amide. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, 1H NMR, 13C NMR and Ms spectral data. All the compounds were tested in-vitro antihuman breast cancer cell line (MCF7). Compounds 18, 8, 41 and 28 with IC50 values of 48.01, 49.11, 49.27 and 49.78 µM, respectively, exhibited better activity than doxorubicin (DOX) as a reference drug with IC50 value of 68.6 µM. Molecular Operating Environment (MOE) performed virtual screening using molecular docking studies of the synthesized compounds. The results indicated that some synthesized compounds suitable inhibitor against dihydrofolate reductase (DHFR) enzyme (PDB ID: 4DFR) with further modification.