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Development of a practical synthesis of etravirine via a microwave-promoted amination
BACKGROUND: Etravirine (ETV) was approved as the second generation drug for use in individuals infected with HIV-1 in 2008 by the U.S. FDA with its unique antiviral activity, high specificity, and low toxicity. However, there are some shortcomings of the existing synthetic routes, such as the long r...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer International Publishing
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6768033/ https://www.ncbi.nlm.nih.gov/pubmed/30569261 http://dx.doi.org/10.1186/s13065-018-0504-4 |
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author | Feng, Da Wei, Fenju Wang, Zhao Kang, Dongwei Zhan, Peng Liu, Xinyong |
author_facet | Feng, Da Wei, Fenju Wang, Zhao Kang, Dongwei Zhan, Peng Liu, Xinyong |
author_sort | Feng, Da |
collection | PubMed |
description | BACKGROUND: Etravirine (ETV) was approved as the second generation drug for use in individuals infected with HIV-1 in 2008 by the U.S. FDA with its unique antiviral activity, high specificity, and low toxicity. However, there are some shortcomings of the existing synthetic routes, such as the long reaction time and poor yield. RESULTS: This article describes our efforts to develop an efficient, practical, microwave-promoted synthetic method for one key intermediate of ETV, which is capable of being operated on a scale-up synthesis level. Through this optimized synthetic procedure, the amination reaction time decreased from 12 h to 15 min and the overall yield improved from 30.4 to 38.5%. CONCLUSION: Overall, we developed a practical synthesis of ETV via a microwave-promoted method, and the synthetic procedure could be amenable to scale-up, and production costs could be significantly lowered. |
format | Online Article Text |
id | pubmed-6768033 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Springer International Publishing |
record_format | MEDLINE/PubMed |
spelling | pubmed-67680332019-10-03 Development of a practical synthesis of etravirine via a microwave-promoted amination Feng, Da Wei, Fenju Wang, Zhao Kang, Dongwei Zhan, Peng Liu, Xinyong Chem Cent J Research Article BACKGROUND: Etravirine (ETV) was approved as the second generation drug for use in individuals infected with HIV-1 in 2008 by the U.S. FDA with its unique antiviral activity, high specificity, and low toxicity. However, there are some shortcomings of the existing synthetic routes, such as the long reaction time and poor yield. RESULTS: This article describes our efforts to develop an efficient, practical, microwave-promoted synthetic method for one key intermediate of ETV, which is capable of being operated on a scale-up synthesis level. Through this optimized synthetic procedure, the amination reaction time decreased from 12 h to 15 min and the overall yield improved from 30.4 to 38.5%. CONCLUSION: Overall, we developed a practical synthesis of ETV via a microwave-promoted method, and the synthetic procedure could be amenable to scale-up, and production costs could be significantly lowered. Springer International Publishing 2018-12-20 /pmc/articles/PMC6768033/ /pubmed/30569261 http://dx.doi.org/10.1186/s13065-018-0504-4 Text en © The Author(s) 2018 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated. |
spellingShingle | Research Article Feng, Da Wei, Fenju Wang, Zhao Kang, Dongwei Zhan, Peng Liu, Xinyong Development of a practical synthesis of etravirine via a microwave-promoted amination |
title | Development of a practical synthesis of etravirine via a microwave-promoted amination |
title_full | Development of a practical synthesis of etravirine via a microwave-promoted amination |
title_fullStr | Development of a practical synthesis of etravirine via a microwave-promoted amination |
title_full_unstemmed | Development of a practical synthesis of etravirine via a microwave-promoted amination |
title_short | Development of a practical synthesis of etravirine via a microwave-promoted amination |
title_sort | development of a practical synthesis of etravirine via a microwave-promoted amination |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6768033/ https://www.ncbi.nlm.nih.gov/pubmed/30569261 http://dx.doi.org/10.1186/s13065-018-0504-4 |
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