Synthesis of (+/-)-thia-calanolide A, its resolution and in vitro biological evaluation
| Title | Synthesis of (+/-)-thia-calanolide A, its resolution and in vitro biological evaluation |
| Publication Type | Journal Article |
| Year of Publication | 2016 |
| Authors | Chopade, AU, Chopade, MU, Chanda, BM, Sawaikar, DD, Sonawane, KB, Gurjar, MK |
| Journal | Arabian Journal of Chemistry |
| Volume | 9 |
| Pagination | S1597-S1602 |
| Date Published | NOV |
| Abstract | 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. (C) 2012 Production and hosting by Elsevier B.V. on behalf of King Saud University. |
| DOI | 10.1016/j.arabjc.2012.04.027 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.613 |
Divison category:
Organic Chemistry