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生物质衍生的糠醇衍生物用于合成碳环核苷膦酸酯类似物的重新评估。

Revaluation of biomass-derived furfuryl alcohol derivatives for the synthesis of carbocyclic nucleoside phosphonate analogues.

作者信息

Sidi Mohamed Bemba, Périgaud Christian, Mathé Christophe

机构信息

Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, Université de Montpellier, CNRS, ENSCM, cc 1705, Site Triolet, Place Eugène Bataillon, 34095 Montpellier cedex 5, France.

出版信息

Beilstein J Org Chem. 2017 Feb 9;13:251-256. doi: 10.3762/bjoc.13.28. eCollection 2017.

DOI:10.3762/bjoc.13.28
PMID:28326134
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5331271/
Abstract

The racemic synthesis of new carbocyclic nucleoside methylphosphonate analogues bearing purine bases (adenine and guanine) was accomplished using bio-sourced furfuryl alcohol derivatives. All compounds were prepared using a Mitsunobu coupling between the heterocyclic base and an appropriate carbocyclic precursor. After deprotection, the compounds were evaluated for their activity against a large number of viruses. However, none of them showed significant antiviral activity or cytotoxicity.

摘要

利用生物来源的糠醇衍生物完成了带有嘌呤碱基（腺嘌呤和鸟嘌呤）的新型碳环核苷甲基膦酸酯类似物的外消旋合成。所有化合物均通过杂环碱基与合适的碳环前体之间的 Mitsunobu 偶联反应制备。脱保护后，对这些化合物针对多种病毒的活性进行了评估。然而，它们均未表现出显著的抗病毒活性或细胞毒性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/53d73d086f99/Beilstein_J_Org_Chem-13-251-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/d98df4737887/Beilstein_J_Org_Chem-13-251-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/21eb3ed84a45/Beilstein_J_Org_Chem-13-251-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/3eed3e2e6afc/Beilstein_J_Org_Chem-13-251-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/d5f159188afc/Beilstein_J_Org_Chem-13-251-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/086f4116f04b/Beilstein_J_Org_Chem-13-251-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/167a7b6775eb/Beilstein_J_Org_Chem-13-251-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/3c2a6b7df1d3/Beilstein_J_Org_Chem-13-251-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/53d73d086f99/Beilstein_J_Org_Chem-13-251-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/d98df4737887/Beilstein_J_Org_Chem-13-251-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/21eb3ed84a45/Beilstein_J_Org_Chem-13-251-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/3eed3e2e6afc/Beilstein_J_Org_Chem-13-251-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/d5f159188afc/Beilstein_J_Org_Chem-13-251-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/086f4116f04b/Beilstein_J_Org_Chem-13-251-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/167a7b6775eb/Beilstein_J_Org_Chem-13-251-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/3c2a6b7df1d3/Beilstein_J_Org_Chem-13-251-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/357d/5331271/53d73d086f99/Beilstein_J_Org_Chem-13-251-g009.jpg

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本文引用的文献

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Enantioselective synthesis of 4-heterosubstituted cyclopentenones.手性合成 4-杂环取代环戊烯酮。
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Design, synthesis, and anti-HIV activity of 4'-modified carbocyclic nucleoside phosphonate reverse transcriptase inhibitors.4'-修饰的碳环核苷膦酸酯逆转录酶抑制剂的设计、合成及抗HIV活性
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将生物质转化为化学品的化学途径。
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