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

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Chinese Journal of Structural Chemistry 2017年第5期36卷 745-750页

作者： MUHAMMAD Danish RABIA Ayub Butt MUHAMMAD Nawaz Tahir MUHAMMAD Ashfaq syeda tahira hafeez Department of Chemistry University of GujratGujrat 50700Pakistan Department of Physics University of SargodhaSargodhaPakistan

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

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

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Chinese Journal of Structural Chemistry 2017年第8期36卷 1307-1314页

作者： MUHAMMAD Danish RABIA Ayub Butt MUHAMMAD Nawaz Tahir MUHAMMAD Ashfaq syeda tahira hafeez MUHAMMAD Naeem Ahmed HALEEMA Qureshi Department of Chemistry University of Gujrat Gujrat 50700 Pakistan Department of Physics University of Sargodha Sargodha Pakistan Department of Chemistry University of Azad Jammu and Kashmir Muzaffarabad 13100 Pakistan

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.

关键词： sulfonamide tranexamic acid 4-chlorobenzenesulfonyl chloride XRD biological applications

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