Design, Synthesis and Biological Evaluation of Pentacyclic Triterpene Dimers as HCV Entry Inhibitors
A series of triterpene dimers bearing different scaffold were designed and synthesized via CuAAC reaction. Their anti-HCV entry activities were evaluated by HCVpp and VSVpp entry assays. It was found that echinocystic acid （EA） and its dimer were still necessary for maintaining anti-HCV entry activi...
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| Veröffentlicht in: | Chinese journal of chemistry 2017-08, Vol.35 (8), p.1322-1328 |
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| container_end_page | 1328 |
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| container_title | Chinese journal of chemistry |
| container_volume | 35 |
| creator | Meng, Lingkuan Wang, Qi Tang, Tao Xiao, Sulong Zhang, Lihe Zhou, Demin Yu, Fei |
| description | A series of triterpene dimers bearing different scaffold were designed and synthesized via CuAAC reaction. Their anti-HCV entry activities were evaluated by HCVpp and VSVpp entry assays. It was found that echinocystic acid （EA） and its dimer were still necessary for maintaining anti-HCV entry activity, and replacement of EA by other triterpenes might significantly decrease its anti-viral activities. Using a linker bearing a piperazine group, compound 14 dramatically increased its potency with IC50 at 2.87 nmol/L. In addition, the undesired hemolytic effect of all these compounds was removed. |
| doi_str_mv | 10.1002/cjoc.201700272 |
| format | Article |
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Their anti-HCV entry activities were evaluated by HCVpp and VSVpp entry assays. It was found that echinocystic acid （EA） and its dimer were still necessary for maintaining anti-HCV entry activity, and replacement of EA by other triterpenes might significantly decrease its anti-viral activities. Using a linker bearing a piperazine group, compound 14 dramatically increased its potency with IC50 at 2.87 nmol/L. In addition, the undesired hemolytic effect of all these compounds was removed.</description><identifier>ISSN: 1001-604X</identifier><identifier>EISSN: 1614-7065</identifier><identifier>DOI: 10.1002/cjoc.201700272</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag GmbH & Co. KGaA</publisher><subject>Antiviral agents ; Chemical synthesis ; dimer ; Dimers ; echinocystic acid ; HCV entry inhibitor ; pentacyclic triterpene ; Piperazine ; Triterpenes ; 丙型肝炎病毒 ; 二聚体 ; 五环三萜 ; 反应合成 ; 抑制剂 ; 抗病毒活性 ; 生物学评价 ; 设计</subject><ispartof>Chinese journal of chemistry, 2017-08, Vol.35 (8), p.1322-1328</ispartof><rights>2017 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 SIOC, CAS, Shanghai & WILEY-VCH Verlag GmbH & Co. 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Their anti-HCV entry activities were evaluated by HCVpp and VSVpp entry assays. It was found that echinocystic acid （EA） and its dimer were still necessary for maintaining anti-HCV entry activity, and replacement of EA by other triterpenes might significantly decrease its anti-viral activities. Using a linker bearing a piperazine group, compound 14 dramatically increased its potency with IC50 at 2.87 nmol/L. In addition, the undesired hemolytic effect of all these compounds was removed.</description><subject>Antiviral agents</subject><subject>Chemical synthesis</subject><subject>dimer</subject><subject>Dimers</subject><subject>echinocystic acid</subject><subject>HCV entry inhibitor</subject><subject>pentacyclic triterpene</subject><subject>Piperazine</subject><subject>Triterpenes</subject><subject>丙型肝炎病毒</subject><subject>二聚体</subject><subject>五环三萜</subject><subject>反应合成</subject><subject>抑制剂</subject><subject>抗病毒活性</subject><subject>生物学评价</subject><subject>设计</subject><issn>1001-604X</issn><issn>1614-7065</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkM1LwzAYxosoOKdXz0GvdiZpmrZH7aabDCY4xVtJ06TL6JIt6ZT-96ZMhjcv7wc8v_fhfYLgGsERghDf87XhIwxR4pcEnwQDRBEJE0jjUz9DiEIKyed5cOHcupckmA6CaiycqvUdeOt0u_KzA0xX4FGZxtSKswZMvlizZ60yGhgJXoVuGe94ozhYWtUKuxVagLHaCOtRB6b5B5jo1nZgpleqVK2x7jI4k6xx4uq3D4P3p8kyn4bzxfMsf5iHPEoRDmVWxWlFEUc4jggrUSmTVFQYyjImAkVlJimERMqEoSgjtBRZ6Z8gokIpIhRGw-D2cHdrzW4vXFuszd5qb1mgDGeE-NqrRgcVt8Y5K2SxtWrDbFcgWPRJFn2SxTFJD2QH4Fs1ovtHXeQvi_wve_NrtjK63ildH3maRDijJMXRD8Cjgtg</recordid><startdate>201708</startdate><enddate>201708</enddate><creator>Meng, Lingkuan</creator><creator>Wang, Qi</creator><creator>Tang, Tao</creator><creator>Xiao, Sulong</creator><creator>Zhang, Lihe</creator><creator>Zhou, Demin</creator><creator>Yu, Fei</creator><general>WILEY-VCH Verlag GmbH & Co. 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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Antiviral agents Chemical synthesis dimer Dimers echinocystic acid HCV entry inhibitor pentacyclic triterpene Piperazine Triterpenes 丙型肝炎病毒 二聚体 五环三萜 反应合成 抑制剂 抗病毒活性 生物学评价 设计 |
| title | Design, Synthesis and Biological Evaluation of Pentacyclic Triterpene Dimers as HCV Entry Inhibitors |
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