Syntheses of Novel Isopenam and Isocephem Antibiotics. Preparation of a retinamido derivative of a highly strained b-lactam as potent anticancer agent

Syntheses of Novel Isopenam and Isocephem Antibiotics. Preparation of a retinamido derivative of a highly strained b-lactam as potent anticancer agent

Syntheses of the cis-configurated isopenam 9 (Scheme 1), isocephem 14 (Scheme 2), and isocephem 19 (Scheme 3) are described. The key step in the preparation of 14 and 19 involved a Pummerer-type rearrangement of the corresponding sulfoxides 12 and 18. These -lactams were found to possess biological...

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Veröffentlicht in:Helvetica chimica acta 1992-10, Vol.75 (6), p.1840-1847
Hauptverfasser: Hakimelahi, Gholam H, Shiao, Min-Jen, Hwu, Jih Ru, Davari, Hady
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container_issue 6
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container_title Helvetica chimica acta
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creator Hakimelahi, Gholam H
Shiao, Min-Jen
Hwu, Jih Ru
Davari, Hady
description Syntheses of the cis-configurated isopenam 9 (Scheme 1), isocephem 14 (Scheme 2), and isocephem 19 (Scheme 3) are described. The key step in the preparation of 14 and 19 involved a Pummerer-type rearrangement of the corresponding sulfoxides 12 and 18. These -lactams were found to possess biological activity against several pathogenic microorganisms in vitro. The electronic activation of the lactam moiety of 19 remarkably enhanced its biological activity. A retinoic moiety was attached to 19 via an amino linker. The resultant retinamido-lactam 21 showed significant cytostatic activity in tracheal organ cultures obtained from vitamin-A-deficient hamsters.
doi_str_mv 10.1002/hlca.19920750610
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title Syntheses of Novel Isopenam and Isocephem Antibiotics. Preparation of a retinamido derivative of a highly strained b-lactam as potent anticancer agent
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