Macrocyclic organotin(IV) carboxylates based on benzenedicarboxylic acid derivatives: Syntheses, crystal structures and antitumor activities

Six new organotin carboxylates based on 1,3-benzenedicarboxylic acid and 1,4-benzenedicarboxylic acid derivatives, namely (Ph(3)Sn)(2)(2,5-L(1))(C(2)H(5)OH)(2) (1) (2,5-H(2)L(1) = 2,5-dibenzoylterephthalic acid), (Ph(3)Sn)(2)(2,5-L(2))(C(2)H(5)OH)(2) (2) (2,5-H(2)L(2) = 2,5-bis(4-methylbenzoyl)terephthalic acid), (Ph(3)Sn)(2)(2,5-L(3))(C(2)H(5)OH)(2) (3) (2,5-H(2)L(3) = 2,5-bis(4-ethylbenzoyl)terephthalic acid), [(n-Bu(2)Sn)(4)(4,6-L(1))O(2)(OH)(OC(2)H(5))](2)center dot 2(C(2)H(5)OH) (4) (4,6- H(2)L(1) = 4,6-dibenzoylisophthalic acid), [(n-Bu(2)Sn)(4)(4,6-L(1))O(2)(OH)(OC(4)H(9))](2)center dot 2(C(4)H(9)OH) (5) and [(n-Bu(2)Sn)(4)(4,6-L(2))O(2)(OH)(OC(2)H(5))](2)center dot 2(C(2)H(5)OH) (6) (4,6-H(2)L(2) = 4,6-bis(4-methylbenzoyl)isophthalic acid), have been synthesized. All the organotin carboxylates have been characterized by elemental analysis, IR, (1)H and (13)C NMR spectroscopy and X-ray crystallography diffraction analyses. The structural analysis reveals that complexes 1-3 show similar structures, containing binuclear triorganotin skeletons. The significant intermolecular O-H center dot center dot center dot O hydrogen bonds linked the complexes 1-3 to form a novel 2D network polymer with 38-member macrocycles. In complexes 4-6, two Sn(4)O(4) ladders are connected by two 1,3-benzenedicarboxylic acid derivatives to yield ladder-like octanuclear architectures and form macrocycle with 24 atoms. In addition, the antitumor activities of complexes 1-6 have been studied. (C) 2011 Elsevier B.V. All rights reserved.