Synthesis, Spectroscopic Studies, and Crystal Structures of Phenylorganotin Derivatives with [Bis(2,6-dimethylphenyl)amino]benzoic Acid: Novel Antituberculosis Agents
✍ Scribed by Vaso Dokorou; Dimitra Kovala-Demertzi; Jerry P. Jasinski; Angeliki Galani; Mavroudis A. Demertzis
- Publisher
- John Wiley and Sons
- Year
- 2004
- Tongue
- German
- Weight
- 237 KB
- Volume
- 87
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
The novel triphenyl adduct of 2‐[(2,6‐dimethylphenyl)amino]benzoic acid (HDMPA; 1), i.e., [SnPh~3~(DMPA)] (2), the dimeric tetraorganostannoxane [Ph~2~(DMPA)SnOSn(DMPA)Ph~2~]~2~ (3), and the monomeric adduct [SnPh~2~(DMPA)~2~] (4), where DMPA is monodeprotonated HDMPA, have been prepared and structurally characterized by means of IR, ^1^H‐NMR, and ^13^C‐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 Ph~3~Sn coordinated to the carboxylato group. Significant CH/π interactions and intramolecular H‐bonds stabilize the structures of 1 and 2, which self‐assembled via CH/π and π/π‐stacking interactions. The Ph~3~Sn 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.