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4-((4-Chlorophenylsulfonamido)methyl)cyclohexanecarboxylic Acid: Synthesis, Crystal Structure and Biological Activities

4-((4-Chlorophenylsulfonamido)methyl)cyclohexanecarboxylic Acid: Synthesis, Crystal Structure and Biological Activities
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摘要 In this study, a novel 4-((4-chlorophenylsulfonamido)methyl)cyclohexanecarboxylic acid(C(14)H(18)ClNO4S) was synthesized by the reaction of tranexamic acid and 4-chlororbenzene sulfonyl chloride in basic medium at room temperature. The molecular structure was determined by FT-IR, NMR, elemental analysis and single-crystal X-ray analysis. The compound crystallizes in the monoclinic system, space group P21/c with a = 12.3120(11), b = 16.5987(19), c = 7.6873(7) ?, β = 90.495(6)o, Z = 4 and V = 1570.9(3) ?~3, crystal size(mm) = 0.38 × 0.16 × 0.14 and Rint = 0.045. In this compound, the carboxylic acid A(O(1)/C(1)/C(2)) and the sulfonyl B(O(3)/S(1)/O(4)) moieties are of course planar. The molecules are dimerized due to the O–H…O type of H-bonding with the R22(8) ring motifs. The dimmers are interlinked through C–H…O and N–H…O types of H-bonding. The synthesized compound was screened against four bacterial and two fungal strains and inactive against all strains. Antioxidant activity was checked against DPPH. Enzyme inhibition activity was carried out using three different enzymes and the title compound was more potent α-chymotrypsin inhibitor. In this study, a novel 4-((4-chlorophenylsulfonamido)methyl)cyclohexanecarboxylic acid(C(14)H(18)ClNO4S) was synthesized by the reaction of tranexamic acid and 4-chlororbenzene sulfonyl chloride in basic medium at room temperature. The molecular structure was determined by FT-IR, NMR, elemental analysis and single-crystal X-ray analysis. The compound crystallizes in the monoclinic system, space group P21/c with a = 12.3120(11), b = 16.5987(19), c = 7.6873(7) ?, β = 90.495(6)o, Z = 4 and V = 1570.9(3) ?~3, crystal size(mm) = 0.38 × 0.16 × 0.14 and Rint = 0.045. In this compound, the carboxylic acid A(O(1)/C(1)/C(2)) and the sulfonyl B(O(3)/S(1)/O(4)) moieties are of course planar. The molecules are dimerized due to the O–H…O type of H-bonding with the R22(8) ring motifs. The dimmers are interlinked through C–H…O and N–H…O types of H-bonding. The synthesized compound was screened against four bacterial and two fungal strains and inactive against all strains. Antioxidant activity was checked against DPPH. Enzyme inhibition activity was carried out using three different enzymes and the title compound was more potent α-chymotrypsin inhibitor.
出处 《Chinese Journal of Structural Chemistry》 SCIE CAS CSCD 2017年第8期1307-1314,共8页 结构化学(英文)
基金 project(P-2549)was supported by Higher Education Commission(HEC)Govt.of Pakistan
关键词 SULFONAMIDE tranexamic acid 4-chlorobenzenesulfonyl chloride XRD biological applications sulfonamide tranexamic acid 4-chlorobenzenesulfonyl chloride XRD biological applications
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