An Overview of Forty Years Organotin Chemistry Developed at the Free Universities of Brussels ULB and VUB

Abstract

Esta revisão cobre os principais eixos de pesquisa desenvolvidos nas Universidades Livres de Bruxelas entre 1961 e 2001. Primeiro, introduzimos os conceitos desenvolvidos no campo das reações de quebra das ligações carbono-estanho em compostos RR'R"R"'Sn usando reagentes E-N, obtendo-se R-E e R'R"R"'SnN, em solventes nucleofilos e não nucleofilos. A adição do nucleofilo ao íon metálico é necessária para permitir a quebra da ligação metal-carbono pelo eletrofilo. A reação pode ser caracterizada pela retenção da configuração do carbono quando um retentor cíclico é usado, ou pela inversão de configuração quando este retentor não é efetivo. A estéreo-seletividade de substituições nucleofilas bimoleculares em estanho é também discutida, bem como a (in)estabilidade de várias classes de tri-organo-estanho derivados. Finalmente, a atividade in vitro anti-tumoral promissora dos compostos di-e tri-organo-estanhos solúveis em água é referenciada.This review covers the main axes of research developed at the Free Universities of Brussels between 1961 and 2001. This paper first introduces the concepts developed in the field of the cleavage reactions of carbon-tin bonds of RR'R"R"'Sn compounds by E-N reagents yielding R-E and R'R"R"'SnN in non-nucleophilic and nucleophilic solvents. The addition of a nucleophile at the metal atom is needed for allowing the electrophile to cleave the carbon-metal bond. The reaction can be characterized by retention of configuration at carbon when a cyclic constraint is imposed, or by inversion of configuration when such a constraint is not effective. The stereoselectivity at tin of bimolecular nucleophilic substitutions at tin is also discussed as well as the optical (in)stability of several classes of triorganotin derivatives. In the last part of this review, the promising in vitro antitumour activities of water-soluble di-and triorganotin compounds is covered.

Amino acetate functionalized Schiff base organotin(IV) complexes as anticancer drugs: synthesis, structural characterization, and in vitro cytotoxicity studies

“…Low doses of organotins can exhibit anti-tumoural activity [20][21][22][23][24][25] and have suggested an action mode via gene-mediated pathway in the cancer cells, opening a new research sub-area on organotin(IV) compounds. The chemical and biochemical aspect of DNA inhibition, including biotechnological aspects of organotin(IV) cancer chemotherapy, has also been described [26].…”

Comparative Study on the Antifungal Activity of Some Di- and Tributyltin(IV) Carboxylate Compounds

“…The organotin(IV) compounds continue to be of interest on account of their interesting structural features (Tiekink, 1991;Shahid et al, 2003;Bhatti et al, 2005) and also because of their wide applications as catalysts, antifouling agents, agricultural biocides, antitumor agents and other biological activities (Blunden and Hill, 1990;Bonire et al, 1998;Pellerito and Nagy, 2002;Gielen, 2003). The organotin(IV) compounds are characterized by the presence of at least one covalent Sn -C bond.…”

“…The counter anion is usually chloride, oxide, fluoride, hydroxide, and thiolate (Pellerito and Nagy, 2002). Carboxylate has also been used successfully as counter anion (Bonire et al, 1998;Pellerito and Nagy, 2002;Szorsick et al, 2002;Gielen, 2003).…”

Synthesis, Chemical Characterization and Biological Screening for Cytotoxicity and Antitumor Activity of Organotin (IV) Derivatives of 3,4-Methylenedioxy 6-nitrophenylpropenoic Acid

“…RSn(OH) 2 Cl + 2HL ⎯→ RSn(Cl)L 2 + 2H 2 O (I) R= n-Bu (3) R 2 SnO + 2HL ⎯→ R 2 SnL 2 + H 2 O (II) R = n-Bu (4), n-Oct (6) R 2 SnCl 2 + 2NaL ⎯→ R 2 SnL 2 + 2NaCl (III) R = Me (1), Et (2) R 3 SnCl + NaL ⎯→ R 3 SnL + NaCl (IV) R = n-Bu (5) R 3 Sn(OH)+HL⎯→R 3 SnL+H 2 O (V) R= Cy (7), Ph (8) All the newly synthesized compounds are air stable crystalline solids, soluble in common organic solvents, and their physical data is summarized in Table 1. The structures of these compounds and coordination behavior of metal have been addressed by different analytical techniques such as elemental analysis, multinuclear NMR ( 1 H, 13 C and 119 Sn) and mass spectrometry.…”

“…Organotin (IV) complexes are extensively used as catalysts, stabilizers, biocides, antifouling agents and as wood preservatives [1][2][3][4][5]. Organotin (IV) derivatives of carboxylic acids are of special interest with regards to their methods of synthesis, structural elucidation and biological activity [6][7][8][9].…”