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Stereoselective in ‐ vitro aromatic‐ring oxygenations of chiral 1,4‐benzodiazepin‐2‐ones
Author(s) -
Kolbah Dragutin,
Blažević Nikola,
Hannoun Mohammad,
Kajfež Franjo,
Kovač Tomislav,
Rendić Slobodan,
Šunjić Vitomir
Publication year - 1977
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19770600134
Subject(s) - chemistry , hydroxylation , ring (chemistry) , demethylation , enantiomer , stereochemistry , in vitro , organic chemistry , biochemistry , enzyme , gene expression , dna methylation , gene
Biological N(1)‐demethylation and C(3)‐hydroxylation of two enantiomeric 1,4‐benzodiazepin‐2‐ones 1 and 2 (cf. scheme 2 ) were found to be nonstereoselective. Aromatic‐ring hydroxylation, however, took place in the ( S )‐series only, leading to 3′‐ and 4′‐hydroxylated, N(1)‐demethylated, metabolites ( 54 and 56 , cf. scheme 5 : these structures were unambiguously confirmed by comparing their UV., CD., and mass spectra with those of authentic specimens). Several compounds, theoretically conceivable as products of hydroxylation in the aromatic A‐ring of 1 and 2 by mechanisms including the NIH‐shift (cf. scheme 3 ), were synthesized but none of these compounds was yet isolated from in vitro incubation mixtures.