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Multi‐ 13 C‐labelled inhibitors of tubulin assembly: 5‐substituted methyl N‐(1H‐benzimidazol‐2‐YL)carbamates
Author(s) -
Cheung H. H. Andrew,
Chau Diem Dieu,
Lacey Ernest
Publication year - 1987
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580240802
Subject(s) - chemistry , thiourea , methanol , medicinal chemistry , carbon 13 nmr , carbamate , stereochemistry , organic chemistry
Eight methyl N‐(1H‐benzimidazol‐2‐yl) carbamates with various 5‐substituents were synthesized, each 13 C‐enriched at carbon 2, and the carbonyl and methoxy carbons. Five were prepared by cyclization involving the appropriate 4‐substituted 1,2‐diaminobenzene (C 6 H 5 CO‐, CH 3 CH 2 CH 2 O‐, CH 3 CH 2 S‐, C 6 H 5 S‐ and CH 3 CH 2 CH 2 ‐), and methyl‐ 13 C N‐[imino(methylthio) methyl‐ 13 C]carbamate‐ 13 C or methyl N, N'‐bis(methoxy‐ 13 C‐carbonyl‐ 13 C)carbamimidothionate‐ 13 C. The latter were prepared from commercially available 13 C‐enriched (91‐92 atom %) carbon tetrachloride, methanol, and thiourea. The remaining three (5‐substituents: C 6 H 5 CH(OH)‐, C 6 H 5 SO‐ and CH 3 CH 2 CH 2 SO‐) were prepared by side‐chain reduction or oxidation. The 1 H‐ and 13 C‐NMR, and the methane CI mass spectral data of the products and intermediates are presented.