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Organostannate derivatives of dicyclohexylammonium hydrogen 2,6‐pyridinedicarboxylate: solution/solid‐state 13 C, 119 Sn NMR and in vitro antitumour activity of bis(dicyclohexylammonium) bis(2,6‐pyridinedicarboxylato)dibutylstannate, and the crystal structure of its monohydrate
Author(s) -
Ng Seik Weng,
Kumar Das V. G.,
Holeček Jaroslav,
Lyčka Antonin,
Gielen Marcel,
Drew Michael G. B.
Publication year - 1997
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/(sici)1099-0739(199701)11:1<39::aid-aoc539>3.0.co;2-q
Subject(s) - chemistry , hydrogen bond , crystal structure , crystallography , tin , stereochemistry , molecule , pyridine , pentagonal bipyramidal molecular geometry , chelation , anhydrous , medicinal chemistry , inorganic chemistry , organic chemistry
Bis(dicyclohexylammonium) bis(2,6‐pyridinedicarboxylato)dibutylstannate is assigned seven‐fold coordination at tin on the basis of its 119 Sn CP/MAS NMR chemical shift (δ=−424.9 ppm). The assignment has been corroborated by a crystal structure determination of its monohydrate, whose tin atom has the trans ‐C 2 SnNO 4 pentagonal bipyramidal [Sn–C=2.040(9), 2.067(8) Å; C–Sn–C =168.9(5)°] geometry. One 2,6‐pyridine‐ dicarboxylato group chelates to the tin atom (Sn–O=2.234(4), 2.260(4); Sn–N =2.279(5) Å) whereas the other binds through only one carboxyl –CO 2 end (Sn–O=2.416(5), 2.441(5) Å). Hydrogen bonds link the cation and the stannate into a linear chain parallel to the b ‐axis. The lattice water molecule is hydrogen‐bonded to the free carboxyl end. The anhydrous compound showed higher in vitro antitumor activity than those of carboplatin and cisplatin when screened against breast (MCF‐7, EVSAT), colonic (WiDr), ovarian (IGROV) and renal (A498) carcinoma, and melanoma (M19 MEL) cell lines. © 1997 by John Wiley & Sons, Ltd.