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Synthesis, characterization and cytotoxic activity of 5,10,15,20‐tetrakis[4‐(triorganostannyloxy)phenyl]porphyrins
Author(s) -
Tian Laijin,
Cao Xianxian,
Zhao Yanxiang,
Jiang Jianzhuang,
Liu Xijie
Publication year - 2013
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.2971
Subject(s) - chemistry , trigonal bipyramidal molecular geometry , benzaldehyde , tetrahedral molecular geometry , porphyrin , proton nmr , tin , molecule , stereochemistry , crystal structure , crystallography , pyrrole , nmr spectra database , photochemistry , spectral line , organic chemistry , catalysis , physics , astronomy
5,10,15,20‐Tetrakis[4‐(triorganostannyloxy)phenyl]porphyrins, (R 3 SnO) 4 TPP [2, R = Cy (a), Ph (b), PhC(CH 3 ) 2 CH 2 (c)], have been synthesized by the condensation of 4‐(triorganostannyloxy)benzaldehyde, 4‐(R 3 SnO)C 6 H 4 CHO (1), with pyrrole in the presence of BF 3 followed by oxidation by p ‐chloranil and characterized by means of elemental analysis, IR, UV–visible and NMR ( 1 H, 13 C and 119 Sn) spectra. The results of X‐ray single‐crystal diffraction show that 1a and 1b possess a trans ‐C 3 SnO 2 trigonal bipyramidal geometry with the axial positions occupied by the phenolate oxygen and formyl group oxygen of an adjacent molecule and form a one‐dimensional zigzag chain. In 2a, the macrocyclic core of the porphyrin is coplanar and each tin atom possesses a distorted tetrahedral geometry. These compounds (1 and 2) have potent in vitro cytotoxic activity against two human tumor cell lines – CoLo205 and MCF‐7 – and the activity decreases in the order Ph > Cy > PhC(CH 3 ) 2 CH 2 for the R group bound to tin. Copyright © 2013 John Wiley & Sons, Ltd.
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