A synthesis of (±)-thia-calanolide A, its resolution and in vitro biological evaluation
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...
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| Format: | Article |
| Language: | English |
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Elsevier
2016-11-01
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| Series: | Arabian Journal of Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535212000950 |
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| author | Anil U. Chopade Manojkumar U. Chopade Bhanu M. Chanda Dilip D. Sawaikar Kiran B. Sonawane Mukund K. Gurjar |
| author_facet | Anil U. Chopade Manojkumar U. Chopade Bhanu M. Chanda Dilip D. Sawaikar Kiran B. Sonawane Mukund K. Gurjar |
| author_sort | Anil U. Chopade |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-22T17:26:54Z |
| format | Article |
| id | doaj.art-838ec68b32654374b10ed01f7e56019b |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-22T17:26:54Z |
| publishDate | 2016-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-838ec68b32654374b10ed01f7e56019b2022-12-21T18:18:42ZengElsevierArabian Journal of Chemistry1878-53522016-11-019S2S1597S160210.1016/j.arabjc.2012.04.027A synthesis of (±)-thia-calanolide A, its resolution and in vitro biological evaluationAnil U. Chopade0Manojkumar U. Chopade1Bhanu M. Chanda2Dilip D. Sawaikar3Kiran B. Sonawane4Mukund K. Gurjar5Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, IndiaDepartment of Chemistry, University of Pune, Pune 411007, IndiaDivision of Organic Chemistry, National Chemical Laboratory, Pune 411008, IndiaDivision of Organic Chemistry, National Chemical Laboratory, Pune 411008, IndiaDivision of Organic Chemistry, National Chemical Laboratory, Pune 411008, IndiaDivision of Organic Chemistry, National Chemical Laboratory, Pune 411008, IndiaA 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.http://www.sciencedirect.com/science/article/pii/S1878535212000950ThiocoumarinThia-calanolide AAnti-HIV activityResolution via chiral HPLC |
| spellingShingle | Anil U. Chopade Manojkumar U. Chopade Bhanu M. Chanda Dilip D. Sawaikar Kiran B. Sonawane Mukund K. Gurjar A synthesis of (±)-thia-calanolide A, its resolution and in vitro biological evaluation Arabian Journal of Chemistry Thiocoumarin Thia-calanolide A Anti-HIV activity Resolution via chiral HPLC |
| title | A synthesis of (±)-thia-calanolide A, its resolution and in vitro biological evaluation |
| title_full | A synthesis of (±)-thia-calanolide A, its resolution and in vitro biological evaluation |
| title_fullStr | A synthesis of (±)-thia-calanolide A, its resolution and in vitro biological evaluation |
| title_full_unstemmed | A synthesis of (±)-thia-calanolide A, its resolution and in vitro biological evaluation |
| title_short | A synthesis of (±)-thia-calanolide A, its resolution and in vitro biological evaluation |
| title_sort | synthesis of thia calanolide a its resolution and in vitro biological evaluation |
| topic | Thiocoumarin Thia-calanolide A Anti-HIV activity Resolution via chiral HPLC |
| url | http://www.sciencedirect.com/science/article/pii/S1878535212000950 |
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