Journal article Open Access
Surendra Singh, Alok Pal Jain, Amit Nayak
Objective: The objective of the paper is synthesis and characterization of sulfonamide-thiazole derived acetamide derivatives and evaluated for them for the anticancer potential.
Material and methods: The sulfonamide-thiazole derived acetamide derivatives has been prepared by the two step process, in first step, 2-chloro-N-(4-((2,3-dihydro-4H-1,4-oxazin-4-yl)sulfonyl)phenyl) acetamide (Compound 2) was synthesized, and in step 2, N-(4-((2,3-dihydro-4H-1,4-oxazin-4-yl)sulfonyl)phenyl)-2-((4-substitutedthiazol-2-yl)amino)acet-amide (Compound 3) was synthesized by the reaction of synthesized compound 2 with different 4-substituted thiazol-2-amine to from the final compounds (compound 3). Total eleven compounds have been synthesized and characterized by physicochemical and IR, NMR and MASS spectral analysis. The final compounds (SA-1 to SA-11) have been evaluated for anticancer activity by SRB assay method.
Result and Discussion: The IR spectrum of the compounds (SA-1 to SA-11) has shown the characteristics peak (cm-1) of N-H peak at 3331, N-H peak at 3118, aromatic C-H peak at 3039, C=O peak at 1672, C-H aliphatic peak at 2938, C-Cl peak at 850, C-Br peak at 1018, C-F peak at 1102, N-O peak at 1358 and N=O peak at 1562. The 1HNMR spectra depicted the peak of N-H at 10.25 ppm, Thiazole-H peak at 6.25 ppm, CH2 peak at 4.19. The 13CNMR spectrum denotes the peak in ppm of C=O at 170.5, C=N at 162.3 and CH2 at 45.6. Compound SA-1, mass spectrum has shown peak at m/z = 414.02, which matches the chemical formula C15H15ClN4O4S2. The result data of the synthesized compounds by SRB assay stated the IC50 value of compounds SA-1 (7.7), SA-3 (9.5), SA-4 (14.7) and SA-11 (8.1) has shown better activity as compared to the standard drug paclitaxel (31.1)
Conclusion: The Cl, Br, NO2 and F compounds enhance the activity when it attached to 4-position of the thiazole ring as well as presence of sulfonamide bearing thiazole with addition to electronegative atom enhance the anticancer activity of compounds
Keywords: Anticancer activity, thiazole, sulfonamide, SRB assay, acetamide