Synthesis and biological evaluation of an electronically activated isooxacephem
β Scribed by Gholam H. Hakimelahi; Shwu-Chen Tsay; Hsi-Hwa Tso; Zahra Ramezani; Jih Ru Hwu
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- English
- Weight
- 344 KB
- Volume
- 4
- Category
- Article
- ISSN
- 0968-0896
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β¦ Synopsis
New isooxacephem (+)-3-ethyl 2-hydrogen (6RS,7RS)- 8-oxo-7-(phenylacetamido)-4-oxa-l-azabicyclo[4.2.0] 1) in six steps. This bicyclic 13-1actam was found to possess notable biological activities against several pathogenic microorganisms in vitro, including Staphylococcus aureus 95, S. aureus FDA 209P, Escherichia coli ATCC 39188, Salmonella typhi O-901, Pseudomonas aeruginosa 18S-H, P. aeruginosa 1101-75, and Klebsiella pneumoniae NCTC 418. The electronic activation of the [3-1actam moiety by an ester group plays a prominent role in the biological activity of this novel isooxacephem.
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Three types of novel triptolide analogues with 9,11-olefin (3-5), five-membered unsaturated lactam ring (6-7) or A/B cis ring junction (8-14) were synthesized. Although with 9,11-olefin instead of 9,11-Ξ²-epoxide, compound 4a was much more active than the parent natural triptolide (1) with the lowest
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