Premium
Solid‐state 119 Sn NMR and antitumor activity of bis [1,3‐bis (3‐oxapentamethylenecarbamoylthioacetato)‐1,1,3,3‐tetrabutyl‐1,3‐distannoxare], and the crystal structure of its bis‐ethanol solvate
Author(s) -
Ng Seik Weng,
Hook James M.,
Gielen Marcel
Publication year - 2000
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(200001)14:1<1::aid-aoc930>3.0.co;2-7
Subject(s) - chemistry , dimer , crystallography , crystal structure , trigonal bipyramidal molecular geometry , stereochemistry , molecule , tetragonal crystal system , tin , ethanol , organic chemistry
The 119 Sn cross polarization‐magic angle spinning NMR spectrum of bis[1,3‐bis(3‐oxapentamethylenecarbamoylthioacetato)‐1,1,3,3‐tetrabutyl‐1,3‐distannoxane], {[(C 4 H 9 ) 2 SnO 2 CCH 2 SC(O)N(CH 2 CH 2 ) 2 O] 2 O} 2 , which consists of two resonances of similar chemical shifts and symmetry (δ iso = −152, −202 ppm; asymmetry, κ = 0.38), implies the existence of two five‐coordinate tin sites in the centrosymmetric dimer. The assignment has been corroborated by X‐ray diffraction analysis on the compound that has been crystallized from ethanol; the crystal structure shows two tin atoms in cis ‐C 2 SnO 3 trigonal‐bipyramidal coordination [C‐Sn‐C = 131.5(1), 131.3(2) °]. The analysis also reveals the presence of two lattice ethanol molecules that are hydrogen‐bonded to the dimer [OO = 2.779(5) Å]. When exposed to air, the distannoxane loses ethanol. The unsolvated distannoxane is more active than cis ‐platin when screened against MCF‐7 (mammary cancer), EVSA‐T (mammary cancer), WiDr (colon cancer), IGROV (ovarian cancer), M19 MEL (melanoma), A498 (renal cancer) and H226 (lung cancer) cell lines. Copyright © 2000 John Wiley & Sons, Ltd.