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 RE 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 die 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 RE 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.

Comparative study of structure: activity relationship of di and triorganotin (IV) complexes of monomethyl glutarate

“…Synthesis of dimethyl, diethyl, diphenyl, and dibenzyltin complexes of monomethyl glutarate (1)(2)(3)(4)(5). The monomethyl glutarate (10 mmol) was dissolved in a minimum amount of methanol (25 mL).…”

“…[13][14][15][16][17][18][19][20] However the solubility of di and tri-organotin(IV) carboxylates in water and water-ethanol is poor, therefore many organotin(IV) complexes with carboxylate ligands containing polar subsitituents (hydroxo and oxo groups) have been prepared and studied. [13][14][15][16][17][18][19][20] In a previous paper we described the synthesis of organotin(IV) complexes of maleimidoacetic acid. 21 In the present work we report the synthesis, spectroscopic characterization, antibacterial and various biological activities of a series of di and triorganotin(IV) complexes of monomethyl glutarate.…”

“…[1][2][3][4][5][6][7][8][9][10] In recent years, investigations have been carried out to test their antitumor activity, and it has been observed that indeed several di and triorganotin(IV) species were found to be active against various types of cancer. 11-13. Biological activity of organotin complexes is believed to be independent on the structure of molecule and coordination number of the metal.…”

<i>IN VITRO</i> ACTIVITY AND COMPARATIVE STUDIES OF SOME ORGANOTIN(IV) BENZOATE DERIVATIVES AGAINST LEUKEMIA CANCER CELL, L-1210

“…The structural chemistry of organotin carboxylates has attracted much attention due to their significant cytotoxic effect and relatively high antitumor activity [1][2]. The new development of these compound may lead for the development of new antitumor drugs, which can display another spectrum of antitumor activity [1,3].…”

Organotin(IV) esters of 4-maleimido-benzoic acid: synthesis, characterization and in vitro anti-leishmanial effects

“…2 Organotin(IV) compounds are well-known for their manifold implications, such as tumouricidal, bactericidal and fungicidal activities, and for their interesting structural features. 3 Leishmaniasis is a parasitic disease in tropical countries and the number of leishmanial cases has increased alarmingly during the last decade. Triphenyltin(IV) complexes of salicylanilide thiosemicarbazone have been reported to be effective in vitro and in vivo as anti-leishmanial agents against L. donovani, and considered a good prospect as a therapeutic mediator for leishmaniasis.…”