Hassan Dalil

Dibutyltin perfluoroalkanecarboxylates: synthesis, NMR characterization and in vitro antitumour activity

Three dibutyltin perfluoroalkanecarboxylates have been synthesized, characterized by H-1-, C-13-, F-19- and Sn-117-NMR, Mossbauer, IR and mass spectroscopy. The structure of tetra-n-butylbis(trifluoroacetato)distannoxane has been elucidated by X-ray crystallography. The in vitro antitumour activity of the three compounds against seven human tumour cell lines was found to be as high as or even higher than that for reference compounds used clinically

Di‐ and tri‐organotin derivatives of 3S,4S‐3‐[(R)‐1‐(tert‐butyl‐dimethylsilyloxy)ethyl]‐4‐[(R)‐1‐carboxyethyl]‐2‐azetidinone: synthesis, characterization and in vitro antitumour activity

Di-n-butyl-, triphenyl and tri-n-butyltin derivatives of 3S,4S-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl-4-[(R)-1-carboxyethyl]-2-azetidinone were synthesized and characterized. Their antitumour activity was screened against seven tumoural cell lines of human origin. Copyright (C) 1999 John Wiley & Sons, Ltd.

DI-n-BUTYL-, TRI-n-BUTYL- AND TRIPHENYLTIN STEROIDCARBOXYLATES: SYNTHESIS, NMR CHARACTERIZATION AND IN VITRO ANTITUMOUR ACTIVITY

1 Vrije Universiteit Brüssel, Pleinlaan 2, B-1050 Brussels, Belgium a Department of General and Organic Chemistry, Faculty of Applied Sciences b High Resolution NMR Centre 2 Universite Libre de Bruxelles a Service de Resonance Magnetique, CPI-232, Boulevard du Triomphe, B-1050 Brussels, Belgium b Chimie Organique Physique, Faculte des Sciences, Avenue F. D. Roosevelt, 50, B-1050 Brussels, Belgium 3 Laboratory for Tumor Biology and Pharmacology, Academic Hospital Rotterdam, P. O. Box 2040, NL-3000 CA Rotterdam, the Netherlands 4 Medical Department, Pharmachemie Β. V., Haarlem, the Netherlands 5 Laboratoire de Chimie de la Matiere Condensee, URA CNRS 1466, Tour 54, 5e etage, Universite Pierre et Marie Curie, 4 Place Jussieu, F-75252 Paris Cedex 05 France

Toxicity profiles in vivo in mice and antitumour activity in tumour-bearing mice of di- and triorganotin compounds.

The in vivo toxicity profiles in mice and the antitumour activity in tumour bearing mice were screened for four di-n-butyltin and five triorganotin carboxylates, di-n-butyltin diterebate (5), bis(phenylacetate) (6), bis(deoxycholate) (7), bis(lithocholate) (8), tri-n-butyltin terebate (9), cinnamate (10), and triphenyltin terebate (11). At their maximum tolerated dosis (MTD), no antitumour effect (T/C ~1) was observed for the compounds 5, 7, 9, 10 and 11. The compounds 6 (T/C = 0.51) and 8 (T/C = 0.42) showed clear antitumour activity after single dose administration and might therefore be of interest for further antitumour activity studies.

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

The reaction of hexafluoro-2,2-bis(4-carboxyphenyl)propane with tetrabutyldipropoxydistannoxane, formed in situ from dibutyltin oxide and n-propanol in benzene, yields a compound the structure of which is a strained macrocycle with a single dicarboxylate moiety.

Di-n-Butyl-, Tri-n-Butyl- and Triphenyltin dl-Terebates: Synthesis, Characterization and In Vitro Antitumour Activity.

Di-n-butyltin, tri-n-butyltin and triphenyltin terebates were screened against several human tumour cell lines and found comparably or more active than carboplatin, cis-platin, 5-fluorouracil, methotrexate and doxorubicin, some reference compounds used clinically.

A novel approach to soluble polystyrenes functionalized by tri-n-butyltin carboxylates

The methyl esters (5xa0a and 5xa0b) of two ω-(para styryl)alkanoic acids, 3-p-styryl propionic and 5-p-styryl pentanoic acid, were respectively synthesized from 3-phenyl propionic acid and 5-phenyl pentanoic acid in four reaction steps. These esters have been submitted to radical copolymerization with styrene affording the corresponding copolymers. The methyl ester functions were subsequently converted into the tri-n-butyltin carboxylates using bis(tributyltin) oxide. This approach by-passes complications of radical polymerization inhibition due to the presence of tin in the monomers. It also avoids undesired, uncontrolled early stage polymerization of styryl moieties during the hydrolysis of the methyl esters into the corresponding carboxylic acid precursors of the monomeric tin carboxylates. Finally, it reduces significantly the polymerization time. Characterizations of the tin functionalized polymers in solution and solid state by NMR, IR and thermal techniques allow us to conclude that the tin atoms are tetracoordinated.

Organotin gibberellates: Synthesis, spectroscopic characterization and antitumour activity

The synthesis and characterization of di-n-butyl-, tri-n-butyl- and triphenyltin gibberellates are reported. Their antitumour activities in vitro against a panel of seven human tumour cell lines are given and compared with those of drugs used clinically

Synthesis, Characterization and Antitumour Activities of Di-n-Butyl- and Dimethyltin D-(+)-Camphorates

The synthesis and characterization di-n-butyland dimethyltin D-(+)-camphorates, respectively compounds 1 and 2, are reported. Compound 1 displays antitumoural activity in vitro, and is more active than cisplatin, 5-fluorouracil and etoposide against seven tumoural cell lines of human origin, but less active than methotrexate and doxorubucin. Several diorganotin derivatives of dicarboxylic acids are active in vitro against human tumoural cell lines1-6. Nevertheless, diorganotin derivatives of dicarboxylic acids with proven antitumour activity in vitro remain rather rare. The present paper reports the synthesis and characterization of two novel diorganotin dicarboxylates, di-n-butyland dimethyltin D-(+)-camphorates, in order to further investigate the influence of the structure of such a dicarboxylate moiety on antitumour properties7. The antitumour activity of the di-n-butyltin compound is presented, that of the dimethyltin compound being provided for comparison. Di-n-butyland dimethyltin D-(+)-camphorates, respectively compounds 1 and 2, were prepared by condensing the appropriate diorganotin oxide with camphoric acid in refluxing toluene/ethanol 4/1 under elimination of the azeotrope water/toluene/ethanol81. They were recrystallized from ethanol/petroleum ether, m.p. 138-140 C, yield 90%, and methylene chloride/hexane, m.p. 258259 C, yield: 96%, respectively. The MSssbauer parameters of compounds 1 and 2 are respectively I.S. 1.39, Q.S.’ 3.32, ]-’1: 1.06, 12:0.92 and I.S. 1.35, Q.S 3.89, FI 0.93, F2 1.02 mm/s. H and 3CNMR data are presented in Table1.

Soluble Polystyrenes Functionalized by Triorgano[(1-oxoalkyl)oxy]stannanes (= Triorganotin Carboxylates): Synthesis, Structure, and Anion-Recognition Characteristics

Polystyrene copolymers of the type (P−H)1−x(P−(CH2)n−COOSnR3)x containing [(1-oxoalkyl)oxy]triphenylstannane or tributyl[(1-oxoalkyl)oxy]stannanes as side chains (P−H=styrene; P−(CH2)n−COOSnR3 =para-substituted styrene-like monomeric unit with R=Ph (x=0.1), Bu (x=0.5); n=2–4) were investigated. The tributyl[(1-oxoalkyl)oxy]stannane copolymer was prepared by direct conversion of the corresponding copolymeric methyl esters with hexabutyldistannoxane. By contrast, the [(1-oxoalkyl)oxy]triphenylstannane copolymer could be prepared only by a procedure involving two reaction steps consisting of a preliminary hydrolysis of the related methyl ester (P−H)1-x(P−(CH2)n−COOMe)x followed by functionalization of the corresponding poly(carboxylic acid) (P−H)1-x(P−(CH2n−COOH)x with hydroxytriphenylstannane. Attempts to directly convert the methyl ester with hydroxytriphenylstannane or hexaphenyldistannoxane led to the formation of uncompletely functionalized product. The structure of the stannane-functionalized polymers was investigated in solution and solid state by NMR, IR, and thermal analysis. The tributylstannane and triphenylstannane copolymers were assessed as chloride-selective anion carriers in polymeric-liquid-membrane potentiometric ion-selective electrodes.