UV Assisted Preliminary DNA Binding Studies and Single-crystal X-ray Structure of 4-{(4-Nitrophenyl-sulfonamido)methyl}cyclohexanecarboxylic Acid  

作　　者：MUHAMMAD Danish RABIA Ayub Butt MUHAMMAD Nawaz Tahir MUHAMMAD Ashfaq SYEDA Tahira Hafeez 

机构地区：[1]Department of Chemistry,University of Gujrat,Gujrat 50700,Pakistan [2]Department of Physics,University of Sargodha,Sargodha,Pakistan

出　　处：《Chinese Journal of Structural Chemistry》2017年第5期745-750,共6页结构化学（英文）

基　　金：This project(P-2549)was supported by Higher Education Commission(HEC)Govt.of Pakistan

摘　　要：A new sulfonamide, 4-{（4-nitrophenylsulfonamido）methyl}cyclohexanecarboxylic acid（C14H18N2O6S）, has been synthesized by the reaction of tranexamic acid and 4-nitrobenzenesulfonyl chloride in basic medium at room temperature. The molecular structure was determined by FT-IR, NMR, elemental analysis and single-crystal X-ray technique. X-ray diffraction shows that the compound crystallizes in the monoclinic system, space group P21/c with a = 13.5980（7）, b = 4.9877（2）, c = 23.3878（13） A, β = 93.254（3）°, Z = 4, V = 1583.67（14） A3, μ = 0.237 mm-1, F（000） = 720, R = 0.0471 and w R = 0.1182. The molecules are related by inversion and paired into dimers via C–H…O interactions. The dimmers are interlinked due to strong N–H…O bonds, where O-atoms are of sulfonyl groups. The molecules are stabilized in the form of infinite two-dimensional network with base vectors [0 1 0] and [0 0 –1] in the plane（1 0 2）. The existence of good intermolecular interactions suggests the biological importance of the synthesized molecule. The compound was screened for its interaction with FS-DNA using UV-visible spectroscopy. UV-visible spectroscopic results depict that the compound interacts with DNA by mixed binding mode intercalation along with hydrogen bonding. Negative values of ΔG（–23.34, –17.79 k J·mol-1） indicate spontaneity of the compound-DNA adduct formation.A new sulfonamide, 4-{（4-nitrophenylsulfonamido）methyl}cyclohexanecarboxylic acid（C14H18N2O6S）, has been synthesized by the reaction of tranexamic acid and 4-nitrobenzenesulfonyl chloride in basic medium at room temperature. The molecular structure was determined by FT-IR, NMR, elemental analysis and single-crystal X-ray technique. X-ray diffraction shows that the compound crystallizes in the monoclinic system, space group P21/c with a = 13.5980（7）, b = 4.9877（2）, c = 23.3878（13） A, β = 93.254（3）°, Z = 4, V = 1583.67（14） A3, μ = 0.237 mm-1, F（000） = 720, R = 0.0471 and w R = 0.1182. The molecules are related by inversion and paired into dimers via C–H…O interactions. The dimmers are interlinked due to strong N–H…O bonds, where O-atoms are of sulfonyl groups. The molecules are stabilized in the form of infinite two-dimensional network with base vectors [0 1 0] and [0 0 –1] in the plane（1 0 2）. The existence of good intermolecular interactions suggests the biological importance of the synthesized molecule. The compound was screened for its interaction with FS-DNA using UV-visible spectroscopy. UV-visible spectroscopic results depict that the compound interacts with DNA by mixed binding mode intercalation along with hydrogen bonding. Negative values of ΔG（–23.34, –17.79 k J·mol-1） indicate spontaneity of the compound-DNA adduct formation.

关 键 词：SULFONAMIDE tranexamic acid 4-nitrobenzenesulfonyl chloride XRD FS-DNA intercalation 

分 类 号：TQ460.1[化学工程—制药化工]