Synthesis, Spectroscopic Studies, and Crystal Structures of Phenylorganotin Derivatives with [Bis(2,6‐dimethylphenyl)amino]benzoic Acid: Novel Antituberculosis Agents

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.

The triphenyltin(VI) complexes of NSAIDs and derivatives. Synthesis, crystal structure and antiproliferative activity. Potent anticancer agents

“…The triphenyltin(IV) complexes Ph 3 Sn (dmpa) (6) and [Ph 3 Sn(mef)] (8) were synthesized by the reaction of (Hmef) or (Hdmpa) with Ph 3 SnOH in a molar ratio of 1:1 according to published procedure [13,14]. …”

“…The crystal structures of triphenyltin(IV) esters of mefenamic acid, meclofenamic (9) and Hdmpa (5) have been also reported and were tested for antimycobacterial activity against Mycobacterium tuberculosis H37Rv. These triphenyltin esters were found to be very good anti-tuberculosis agents [11][12][13][14].…”

Synthesis, characterization, and in vitro antimicrobial activities of organotin(IV) complexes of Schiff bases with ONO‐type donor atoms

“…Recent studies have focused on their biological [14], particularly antitumor [15][16][17][18], antibacterial [18][19][20][21], antifungal [21,22], and antitubercular, properties [23,24]. Many in vitro studies have been performed to explain the mechanism responsible for the biological activity of these agents.…”

Heptacoordinate Tin(IV) Compounds Derived from Pyridine Schiff Bases: Synthesis, Characterization, in Vitro Cytotoxicity, Anti-inflammatory and Antioxidant Activity

“…3) Among the most studied organotin(IV) complexes a special emphasis has been placed on the study of carboxylates as potential metallotherapeutic drugs, 4) however, a wide spectrum of biological activities such as anti-microbial, [5][6][7][8][9][10] anti-inflammatory, [11][12][13][14][15] anti-fungal, 14) cardiovascular, 5,10,16,17) anti-tuberculosis 18,19) and biocide among others remains a subject of intense study. 20) Schiff bases are of paramount importance as ligands in metal coordination chemistry as they form stable complexes with most of transition metals.…”