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Synthesis of Thione Analogues of Monobactams
Author(s) -
Nieschalk Jens,
Schaumann Ernst
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960123
Subject(s) - chemistry , reagent , demethylation , side chain , nitrogen atom , moiety , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , ring (chemistry) , gene expression , dna methylation , gene , polymer
Optically active β‐lactams 4 were treated with Lawesson's reagent ( 2 ) or Davy's reagent ( 3 ) to give the β‐thiolactams 5 . Demethylation of 5 by reduction with dissolved metal gave the 1‐unsubstituted 2‐azetidinethiones 6 which were sulfonated and Boc‐deprotected to provide (3 S )‐amino‐2‐thiomonobactamic acids 8 . The side chain on nitrogen was introduced by using 1‐hydroxybenzotriazole‐activated acids 9 . Deprotection of functional groups in the side chain yielded the β‐thiolactam analogues 11a, 11b of SQ 81,377 and aztreonam ( 1 ). These compounds were found to be weakly active against a range of Gram‐negative bacteria.