Williams David E, Bottriell Helen, Davies Julian, Tietjen Ian, Brockman Mark A, Andersen Raymond J
Departments of Chemistry and Earth & Ocean Sciences, University of British Columbia , Vancouver, BC, Canada V6T 1Z1.
Life Sciences Institute, Department of Microbiology and Immunology, University of British Columbia , Vancouver, BC, Canada V6T 1Z3.
Org Lett. 2015 Nov 6;17(21):5304-7. doi: 10.1021/acs.orglett.5b02664. Epub 2015 Oct 14.
Unciaphenol (2), an oxygenated analogue of the Bergman cyclization product of the enediyne uncialamycin (1), has been isolated along with 1 from cultures of the actinomycete Streptomyces uncialis. It is proposed that the C-22 OH substituent in 2 might arise from the attack of a nucleophilic oxygen species on the p-benzyne diradical intermediate IA in the Bergman cyclization of 1. 2 shows in vitro anti-HIV activity against viral strains that are resistant to clinically utilized anti-retroviral therapies.
钩孢酚（2）是烯二炔钩孢霉素（1）的伯格曼环化产物的氧化类似物，它与1一起从放线菌钩孢链霉菌的培养物中分离得到。有人提出，2中C-22位的羟基取代基可能源于亲核氧物种对1在伯格曼环化反应中对苯炔双自由基中间体IA的攻击。2对临床上使用的抗逆转录病毒疗法耐药的病毒株具有体外抗HIV活性。
