A synthesis of (±)-thia-calanolide A, its resolution and in vitro biological evaluation

Autor: Anil U. Chopade, Manojkumar U. Chopade, Bhanu M. Chanda, Dilip D. Sawaikar, Kiran B. Sonawane, Mukund K. Gurjar
Jazyk: angličtina
Rok vydání: 2016
Předmět:
Zdroj: Arabian Journal of Chemistry, Vol 9, Iss S2, Pp S1597-S1602 (2016)
Druh dokumentu: article
ISSN: 1878-5352
DOI: 10.1016/j.arabjc.2012.04.027
Popis: A synthesis of (±)-thia-calanolide A 3 has been successfully accomplished starting from 3,5-dimethoxythiophenol 4, in six steps in an overall yield of 4.5%. The key reaction involved Friedel–Crafts tigloylation of 5,7-dihydroxy-4-n-propyl thiocoumarin 6 employing an appropriate solvent of CS2–PhNO2 in a ratio of 7:3. In its biological evaluation for anti-HIV activity, (±)-thia-calanolide A 3 demonstrated comparatively less activity with calanolide A and its synthetic analogue aza-calanolide. Further, (±)-3 has been resolved by chiral HPLC to (+) and (−)-3.
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