Synthesis, Bioactivity, and Crystal Structure Analysis of 2-(3-Oxobenzo[d]isothiazol-2(3H)-yl)ethyl Benzoates

Fifteen novel 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)ethyl benzoates were synthesized by the condensation of 2-(2-hydroxyethyl)benzo[d]isothiazol-3(2H)-one with substituted benzoic acids in dichloromethane. All the compounds were characterized by elemental analysis, IR, ESI-MS and H-1 NMR. The crystal structures for 2-(2-hydroxyethyl)benzo[d]isothiazol-3(2H)-one (2) and 2-(3-oxobenzo[d]isothiazol-2(3H)-yl)ethyl 2-methoxybenzoate (3o) have been determined by X-ray crystal structure analysis. Compound 2 (C9H9NO2S) crystallizes in the monoclinic system, space group Pn with a = 10.552(3), b = 7.849(2), c = 10.765(4) angstrom, beta = 103.128(4)degrees, V = 868.3(5) angstrom(3), M-r = 195.24, D-c = 1.493 Mg.m(-3), mu = 0.33 mm(-1), F(000) = 408, Z = 4, R = 0.0314 and wR = 0.0628. Compound 3o (Ci(7)H(15)NO(4)S) crystallizes in the triclinic system, space group P (1) over bar with a = 8.028(2), b = 9.300(2), c = 10.430(3) angstrom, V = 752.1(3) angstrom(3), M-r = 329.36, D-c = 1.454 Mg.m(-3), mu = 0.24 mm(-1), F(000) = 344, Z = 2, R = 0.0377 and wR = 0.0904. The preliminary biological test indicated that the title compounds show better growth inhibitory activity against the gram-positive bacteria than the gram-negative bacteria.