Dialkyltin derivatives of dicarboxylic acids: Synthesis, characterization and in vitro antitumor properties

Abstract

Diorganotin deriuatiws of dicarboxylic acids, including diethyltin propene-l,3-dicarboxylate, diethyltin homophthalate, and di-n-butyltin tetrafluorophthalate, were tested in uitro against two human tumor cell lines, MCF-7, a mammary tumor, and WiDr, a colon carcinoma. Most of these display lower inhibition doses ID,, than cis-platin. The synthesis and characterization of the last three compounds by Mossbauer spectroscopy, 'H, I3C andlor Il9Sn NMR and mass spectrometry, are also presented.

The synthesis, and molecular and crystal structure of diphenyl(2-oxidonaphthylmethyl-iminoacetato)tin(IV)

“…In an encouraging number of instances, the results show the organotins to be more effective than cis-platin or carboplatin (3). Studies of structureactivity relationships have shown that the factors influencing activity may be very subtle differences in bond lengths or bond angles, reinforcing the value of structural investigations in this field (10)(11)(12)(13). Recent reports of the activity of certain diorganotin derivatives of pyridine 2,6-dicarboxylic acid and some related compounds (14,15) against the P388 lymphocytic leukemia tumour, both in vitro and in vivo, led us to report the synthesis and characterization of a series of diorganotin iminodiacetates (16) and diorganotin(1V)-N-arylidene-a-amino acid complexes (17).…”

Di‐n‐butyltin(IV) derivatives of bis(carboxymethyl)benzylamines: synthesis, NMR and X‐ray structure characterization and in vitro antitumour properties

“…[8][9][10] Several papers deal with complexes of various metals containing the carboxylates of iminodiacetic acid, N-methyliminodiacetic acid and some other N-substituted iminodiacetic acids as main ligands. 7,[11][12][13][14][15][16][17][18][19] Among the compounds of Scheme 1, 6,7,19 Ia and Ib did not exhibit any activity in vivo against P388 leukaemia. 6 Compounds Ia, If, Ih, Ii and Ij have been tested in vitro against two human cell lines, MCF-7, a mammary tumour, and WiDr, a colon carcinoma.…”

“…[1][2][3][4][5] However, diorganotin(IV) derivatives of bis(carboxymethyl)amines and some N-substituted analogues have been investigated only to a limited extent. 6,7 This is probably due to the fact that only some ligands are commercially available and methods for their preparation are not numerous. [8][9][10] Several papers deal with complexes of various metals containing the carboxylates of iminodiacetic acid, N-methyliminodiacetic acid and some other N-substituted iminodiacetic acids as main ligands.…”

“…Except for Ih, these compounds display a high antitumour activity since they have significantly lower inhibition doses ID 50 than cisplatin against both cell lines. 7,20 We are interested in the chemistry and antitumour activity of tin complexes derived from ligands of this type. In this paper, we report the synthesis, structure and properties of a novel di-n-butyltin(IV) derivative of bis(carboxymethyl)benzylamine and its three analogues substituted by a methyl group on the phenyl moiety, compounds 1-4 (Scheme 2).…”

The reaction of di-n-butyltin oxide with hexafluoro-2,2-bis(4-carboxyphenyl)propane

“…[1][2][3][4][5] Di-n-butyltin perfluoroalkanecarboxylates also exhibit significant activities in vitro (H. Dalil, M. Biesemans, J. C. Martins, J.-M. Renon, B. Mahieu, D. de Vos, R. Willem and M. Gielen, unpublished results) When dicarboxylic acids react with a diorganotin oxide, they generally lead to a cyclic structure including one tin atom. 6,7 In this paper we investigate whether a rather rigid dicarboxylic acid can give rise upon condensation with di-n-butyltin oxide to a strained cyclic diorganotin dicarboxylate. Hexafluoro-2,2-bis(4-carboxyphenyl)propane 1 was found appropriate for this purpose.…”