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(+)‐(5 R ,6 S )‐2‐(1′‐Aminoalkyl)‐6‐(hydroxyalkyl)penem‐3‐carboxylic Acids
Author(s) -
Lang Marc,
Hungerbühler Ernst,
Schneider Peter,
Scartazzini Riccardo,
Tosch Werner,
Konopka Edward A.,
Zak Oto
Publication year - 1986
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.19860690709
Subject(s) - chemistry , broad spectrum , stereochemistry , antibacterial activity , lactam , threonine , antibiotics , combinatorial chemistry , organic chemistry , bacteria , biochemistry , enzyme , serine , genetics , biology
In continuation of our work on penem antibiotics, novel chiral (5 R ,6 S )‐2‐(1′‐aminoalkyl)‐6‐(hydroxyalkyl)‐derivatives 1 have been synthesized by two essentially different strategies. Whereas the starting materials for 1a ‐ f , azetidinones 2 and 5 , were obtained from chiral building blocks (6‐aminopenicillanic acid and L‐threonine, resp.), the one for 1g , azetidinone 9 , was derived from racemic 4‐acetoxyazetidinone and, as chiral auxiliary, (2 R )‐2‐mercaptopropan‐1‐ol. The 2‐aminomethyl derivatives 1a (CGP 30 779) and 1f (CGP 31 608) proved the most potent compounds in the antibacterial tests in vitro and showed a well‐balanced spectrum of activity by comparison with that of established β‐lactams.