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 CS(2)–PhNO...

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Autores principales: Chopade, Anil U., Chopade, Manojkumar U., Chanda, Bhanu M., Sawaikar, Dilip D., Sonawane, Kiran B., Gurjar, Mukund K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Production and hosting by Elsevier B.V. on behalf of King Saud University. 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7148711/
http://dx.doi.org/10.1016/j.arabjc.2012.04.027
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author Chopade, Anil U.
Chopade, Manojkumar U.
Chanda, Bhanu M.
Sawaikar, Dilip D.
Sonawane, Kiran B.
Gurjar, Mukund K.
author_facet Chopade, Anil U.
Chopade, Manojkumar U.
Chanda, Bhanu M.
Sawaikar, Dilip D.
Sonawane, Kiran B.
Gurjar, Mukund K.
author_sort Chopade, Anil U.
collection PubMed
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 CS(2)–PhNO(2) 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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spelling pubmed-71487112020-04-13 A synthesis of (±)-thia-calanolide A, its resolution and in vitro biological evaluation Chopade, Anil U. Chopade, Manojkumar U. Chanda, Bhanu M. Sawaikar, Dilip D. Sonawane, Kiran B. Gurjar, Mukund K. Arabian Journal of Chemistry Article 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 CS(2)–PhNO(2) 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. Production and hosting by Elsevier B.V. on behalf of King Saud University. 2016-11 2012-05-02 /pmc/articles/PMC7148711/ http://dx.doi.org/10.1016/j.arabjc.2012.04.027 Text en © 2012 Production and hosting by Elsevier B.V. on behalf of King Saud University. Since January 2020 Elsevier has created a COVID-19 resource centre with free information in English and Mandarin on the novel coronavirus COVID-19. The COVID-19 resource centre is hosted on Elsevier Connect, the company's public news and information website. Elsevier hereby grants permission to make all its COVID-19-related research that is available on the COVID-19 resource centre - including this research content - immediately available in PubMed Central and other publicly funded repositories, such as the WHO COVID database with rights for unrestricted research re-use and analyses in any form or by any means with acknowledgement of the original source. These permissions are granted for free by Elsevier for as long as the COVID-19 resource centre remains active.
spellingShingle Article
Chopade, Anil U.
Chopade, Manojkumar U.
Chanda, Bhanu M.
Sawaikar, Dilip D.
Sonawane, Kiran B.
Gurjar, Mukund K.
A synthesis of (±)-thia-calanolide A, its resolution and in vitro biological evaluation
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 Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7148711/
http://dx.doi.org/10.1016/j.arabjc.2012.04.027
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