The synthesis, structural characterization and biocidal properties of some triorganotin(IV) esters ofN-arylidene-?-amino acids.

Abstract

The methods of synthesis, elemental analysis, IR and NMR spectroscopic data and fungicidal activity against Ceratocystis ulmi are reported for a series of triorganotin esters of N‐arylidene‐ω‐amino acids of general formula R3SnOCO(CH2)nN = CHAr (R = Ph, n‐Bu; Ar = 2‐HOC6H4, 2‐HOC10H6; n = 1, 2, 3 and 5). The crystal structures for two of the compounds, tributyltin N‐2‐hydroxynaphthalidene glycinate (1) and tributyltin N‐2‐hydroxynaphthalidene‐β‐alaninate (2), have been determined. Although both of these compounds have a trans‐R3SnO2 structure, in compound 1 the carboxylate group is monodentate and the fifth coordination position around the tin atom is taken up by a coordinated phenolic group, whereas in 2 the carboxylate group is bridging. These two examples thus correspond to the two different structures reported for trans‐R3SnO2 complexes. Both compounds were found to be active against Ceratocystis ulmi, but there was no significant difference in their levels of biological activity against this particular fungus. Apart from compound 1, the other tributyltin compounds reported are believed to adopt the carboxylate bridging mode shown by compound (2). Crystal data: for 1, crystals monoclinic, space group P21/c, a = 12.9435(11) Å, b = 13.5769(10) Å, c = 15.7715(12) Å, β = 108.919(6)°, Z = 4, Rf = 0.046 and Rw = 0.058 for 1448 significant reflections; for 2, crystals monoclinic, space group C 2/c,a = 24.588(14) Å, b = 9.733(3) Å, c = 27.611(12) Å, β = 113.49(4)°, Z = 8, Rf = 0.053 and Rw = 0.069 for 3822 significant reflections. © 1998 John Wiley & Sons, Ltd.

Synthesis and spectroscopic properties of [N-(4-carboxyphenyl) salicylideneiminato] di- and tri-organotin (IV) complexes and crystal structures of {[nBu2Sn(2-OHC6H4CHNC6H4COO)]2O}2 and Ph3Sn(2-OHC6H4CHNC6H4COO)

“…Organotin(IV) complexes with Schiff bases have been the focus all the while owing to their anti-tumour activities [1][2][3][4][5][6][7][8], in particular organotin(IV) esters of Narylidene-amino acids have been observed to exhibit a great anti-tumour activity against human tumour cell lines [9]. Recently studies on the coordination chemistry of amio-acid-derived Schiff bases ligating diorganotin(IV) centers have received some attention [10].…”

Synthesis, characterization, cytotoxic activity and crystal structures of tri- and di-organotin(IV) complexes constructed from the β-{[(E)-1-(2-hydroxyaryl)alkylidene]amino}propionate and β-{[(2Z)-(3-hydroxy-1-methyl-2-butenylidene)]amino}propionate skeletons

“…Furthermore, many organotin(IV) derivatives have been found to possess anticancer activity in a variety of tumour cells and the structures of these organotin(IV) complexes are well characterized in the solid state [20,21]. Organotin(IV) complexes with Schiff bases, such as organotin(IV) esters of N-arylidene-amino acids, have also been shown to exhibit notable antitumour activity against human tumour cell lines [22], as well as fungicidal activity [23]. On the other hand, dialkyltin(IV) compounds have selective effects on lymphocytes [24][25][26], which can be used in cancer chemotherapy or to control other pathological effects.…”

Synthesis and structural characterization of diorganotin(IV) esters of salicylidene-amino acids

“…Recently, organotin(IV) compounds with schiff bases have received increased attention owing to their anti-tumour activities [1][2][3][4][5][6][7][8][9], in particular the organotin(IV) esters of N-arylidene-amino acids have been observed to exhibit a great anti-tumour activity against human tumour cell lines [10]. As an extension of studies of organotin(IV) compounds with schiff bases, we synthesized eight new diorganotin esters of salicylidene-amino acids by the reaction of diorganotin oxide and salicylidene-amino acids in 1:1 stoichiometry.…”