Design and Synthesis of Oleanolic Acid Rings A and C Lactone Derivatives

Yu, Fei; Zheng, Yongxiang; Peng, Yiyun; Zhou, Demin; Xiao, Sulong

doi:10.6023/cjoc204509001

Cited by 2 publications

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“…Compound 10b Starting from compound 10a (195 mg, 0.4 mmol), compound 10b was synthesized using methods published previously. [21] The product was purified by column chromatography [V(PE)/V(EtOAc)＝3/1] to give 10b as a white solid (189 mg, 90%). m.p.…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of Pentacyclic Triterpene Dimers as HCV Entry Inhibitors

et al. 2017

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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 IC 50 at 2.87 nmol/L. In addition, the undesired hemolytic effect of all these compounds was removed.

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Section: Methodsmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of Pentacyclic Triterpene Dimers as HCV Entry Inhibitors

et al. 2017

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“…本课题组前期研究发现, 将 OA 通过 Cu(I)催化叠氮-炔基 Husigen 环加成(CuAAC)反应与葡萄糖偶联形成的缀合物(图 1)较 OA 抗流感活性显著提高(IC 50 ＝5.47 µmol•L -1 ), 同时对奥司他韦耐药毒株也表现出了明显的抑制效果 [15] . Autodock [16][17][18][19][20][21][22][23][24] . [25] .…”

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Design, Synthesis and Anti-influenza A Virus Evaluation of Oleanolic Acid C3-Glycoconjugates

Shao¹,

Yang²,

Li³

et al. 2021

Chinese Journal of Organic Chemistry

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Inhibitors targeting the entry stage of influenza viruses are a hot spot in the development of anti-influenza drugs. Our previous studies showed that oleanolic acid (OA) C28 glycoconjugates displayed strong anti-influenza virus activity. In this paper, a series of oleanolic acid C3 glycoconjugates 7a～14c were designed and synthesized via copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. The anti-influenza activities of all these compounds were evaluated in vitro. Among them, oleanane-12-enyl-28-benzyloxycarbonyl-3-O-(4-methylene-1,2,3-triazole-1-(2,3,4,6-tetra-O-acetyl-β-D-galactoside)) (12a) showed the strongest activity with an IC50 of 12.45 µmol•L -1 , and no obvious cytotoxic effect on MDCK cells was observed at 100 µmol•L -1 . Hemagglutination inhibition and molecular docking experiments indicated that compound 12a might target viral envelope hemagglutinin (HA), thus inhibiting the attachment of viruses to host cells. This study improved the structure-activity relationships of oleanolic acid and its derivatives against influenza virus, and provided a basis for further research on anti-virus by these natural products.

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Design and Synthesis of Oleanolic Acid Rings A and C Lactone Derivatives

Cited by 2 publications

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Design, Synthesis and Biological Evaluation of Pentacyclic Triterpene Dimers as HCV Entry Inhibitors

Design, Synthesis and Biological Evaluation of Pentacyclic Triterpene Dimers as HCV Entry Inhibitors

Design, Synthesis and Anti-influenza A Virus Evaluation of Oleanolic Acid C3-Glycoconjugates

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