Syntheses of Novel Isopenam and Isocephem Antibiotics. Preparation of a retinamido derivative of a highly strained β-lactam as potent anticancer agent
✍ Scribed by Gholam H. Hakimelahi; Min-Jen Shiao; Jih Ru Hwu; Hady Davari
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- German
- Weight
- 499 KB
- Volume
- 75
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Syntheses of the cis-configurated isopenam 9 (Scheme I ) , 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 8-lactams were found to possess biological activity against several pathogenic microorganisms in uitro. 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-8-lactam 21 showed significant cytostatic activity in tracheal organ cultures obtained from vitamin-A-deficient hamsters.