Synthesis,Spectroscopic Studies,and Crystal Structures of Phenylorganotin Derivatives with [Bis(2,6‐dimethylphenyl)amino]benzoic Acid: Novel Antituberculosis Agents |
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Authors: | Vaso Dokorou Dimitra Kovala‐Demertzi JerryP Jasinski Angeliki Galani MavroudisA Demertzis |
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Institution: | Vaso Dokorou,Dimitra Kovala‐Demertzi,Jerry?P. Jasinski,Angeliki Galani,Mavroudis?A. Demertzis |
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Abstract: | The novel triphenyl adduct of 2‐(2,6‐dimethylphenyl)amino]benzoic acid (HDMPA; 1 ), i.e., SnPh3(DMPA)] ( 2 ), the dimeric tetraorganostannoxane Ph2(DMPA)SnOSn(DMPA)Ph2]2 ( 3 ), and the monomeric adduct SnPh2(DMPA)2] ( 4 ), where DMPA is monodeprotonated HDMPA, have been prepared and structurally characterized by means of IR, 1H‐NMR, and 13C‐NMR spectroscopy. The structures of 1 and 2 have been determined by X‐ray crystallography. Single‐crystal X‐ray‐diffraction analysis of 1 revealed that there are two molecules in the asymmetric unit, HD1 and HD2 , differing in conformation, both forming centrosymmetric dimers linked by H‐bonds between the carboxylic O‐atoms. X‐Ray analysis of 2 revealed a pentacoordinate structure containing Ph3Sn coordinated to the carboxylato group. Significant C? H/π interactions and intramolecular H‐bonds stabilize the structures of 1 and 2 , which self‐assembled via C? H/π and π/π‐stacking interactions. The Ph3Sn adduct 2 was found to be a promising antimycobacterial lead compound, displaying activity against Mycobacterium tuberculosis H37Rv. The cytotoxiciy in the Vero cell line is also reported. |
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