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Synthesis, Spectroscopic Studies, and Crystal Structures of Phenylorganotin Derivatives with [Bis(2,6‐dimethylphenyl)amino]benzoic Acid: Novel Antituberculosis Agents
Author(s) -
Dokorou Vaso,
KovalaDemertzi Dimitra,
Jasinski Jerry P.,
Galani Angeliki,
Demertzis Mavroudis A.
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490175
Subject(s) - chemistry , adduct , benzoic acid , intramolecular force , crystal structure , monomer , antimycobacterial , stereochemistry , molecule , crystallography , stacking , nuclear magnetic resonance spectroscopy , medicinal chemistry , mycobacterium tuberculosis , organic chemistry , medicine , tuberculosis , pathology , polymer
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.