Synthesis and evaluation of steroidal thiazoline conjugates as potential antiviral agents

被引：13

作者：

Ke, Shaoyong ^{[1
,4
]}

Li, Ni ^{[2
]}

Ke, Ting ^{[3
]}

Shi, Liqiao ^{[1
]}

Zhang, Zhigang ^{[1
]}

Fang, Wei ^{[1
]}

Zhang, Ya-Ni ^{[1
]}

Wang, Kaimei ^{[1
]}

Zhou, Ronghua ^{[1
]}

Wan, Zhongyi ^{[1
]}

Yang, Ziwen ^{[1
]}

Zhang, Guangyang ^{[1
]}

Wei, Yanhong ^{[2
]}

机构：

[1] Hubei Acad Agr Sci, Natl Biopesticide Engn Res Ctr, Hubei Biopesticide Engn Res Ctr, Wuhan 430064, Hubei, Peoples R China

[2] Hubei Univ Technol, Hubei Prov Cooperat Innovat Ctr Ind Fermentat, Hubei Key Lab Ind Microbiol,Minist Educ,Natl Ctr, Key Lab Fermentat Engn,Sino German Biomed Ctr, Wuhan 430068, Hubei, Peoples R China

[3] 1 Middle Sch Lengji, Gucheng 441703, Hubei, Peoples R China

[4] East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

来源：

FUTURE MEDICINAL CHEMISTRY | 2018年 / 10卷 / 22期

基金：

中国国家自然科学基金; 国家重点研发计划;

关键词：

antiviral activity; coxsackie virus type B; dehydroepiandrosterone; enterovirus; 71; steroid; thiazoline; VITRO ANTICANCER EVALUATION; IN-VITRO; BIOLOGICAL EVALUATION; DERIVATIVES SYNTHESIS; DEHYDROEPIANDROSTERONE; EPIANDROSTERONE; REPLICATION; INHIBITION; DISCOVERY; ANALOGS;

D O I：

10.4155/fmc-2018-0075

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Aim: Many heterocyclic compounds derived from natural steroids exhibited broad activities, so this work focused on the investigations on a series of steroidal thiazoline conjugates as antiviral agents. Materials & methods:A series of steroid derivatives containing thiazoline heterocycles were designed and synthesized via a convenient condensation procedure. The compounds were screened for their potential antivirus activities against Enterovirus 71 (EV71) and Coxsackie Virus Type B (CVB3). Results and Conclusion: The in vitro bioassay indicated that compounds 5b, 5g and 5i exhibited excellent antiviral effects on EV71, and compounds 5b, 5e, 6c and 6g presented better antiviral activities against CVB3 compared with the controls ribavirin or pirodavir. These results indicate that these steroidal thiazoline conjugates might be feasible therapeutic candidates against EV71 infection, which might also be considered as promising compounds for optimization of potential antivirus agents.

引用

页码：2589 / 2606

页数：18

共 37 条

[1] Synthesis and Antiviral Activity of New Indole-Based Heterocycles [J].

Abdel-Gawad, Hassan ;

Mohamed, Hanan Ahmed ;

Dawood, Kamal Mohamed ;

Badria, Farid Abdel-Rahem .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (11) :1529-1531

[2] Dehydroepiandrosterone, epiandrosterone and synthetic derivatives inhibit Junin virus replication in vitro [J].

Acosta, Eliana G. ;

Bruttomesso, Andrea C. ;

Bisceglia, Juan A. ;

Wachsman, Monica B. ;

Galagovsky, Lydia R. ;

Castilla, Viviana .

VIRUS RESEARCH, 2008, 135 (02) :203-212

[3]

ALLEY MC, 1988, CANCER RES, V48, P589

[4] Novel 2-Substituted 7-Azaindole and 7-Azaindazole Analogues as Potential Antiviral Agents for the Treatment of Influenza [J].

Bandarage, Upul K. ;

Clarke, Michael P. ;

Perola, Emanuele ;

Gao, Huai ;

Jacobs, Marc D. ;

Tsai, Alice ;

Gillespie, Jeffery ;

Kennedy, Joseph M. ;

Maltais, Francois ;

Ledeboer, Mark W. ;

Davies, Ioana ;

Gu, Wenxin ;

Byrn, Randal A. ;

Addae, Kwame Nti ;

Bennett, Hamilton ;

Leeman, Joshua R. ;

Jones, Steven M. ;

O'Brien, Colleen ;

Memmott, Christine ;

Bennani, Youssef ;

Charifson, Paul S. .

ACS MEDICINAL CHEMISTRY LETTERS, 2017, 8 (02) :261-265

[5] In vitro evaluation of the antiviral properties of Shilajit and investigation of its mechanisms of action [J].

Cagno, Valeria ;

Donalisio, Manuela ;

Civra, Andrea ;

Cagliero, Cecilia ;

Rubiolo, Patrizia ;

Lembo, David .

JOURNAL OF ETHNOPHARMACOLOGY, 2015, 166 :129-134

[6] Antiviral effect of dehydroepiandrosterone on Japanese encephalitis virus infection [J].

Chang, CC ;

Ou, YC ;

Raung, SL ;

Chen, CJ .

JOURNAL OF GENERAL VIROLOGY, 2005, 86 :2513-2523

[7] Synthesis of Dehydroepiandrosteronyl Thiazole Derivatives and Their Antiproliferative Evaluation [J].

Cui, Jianguo ;

Zhao, Dandan ;

He, Dongmei ;

Huang, Yanmin ;

Liu, Zhiping ;

Lin, Qifu ;

Shi, Haixin ;

Gan, Chunfang .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (03) :630-637

[8] Inhibition of human immunodeficiency virus type-1 (HIV-1) replication by Immunor (IM28), a new analog of dehydroepiandrosterone [J].

Diallo, K ;

Loemba, H ;

Oliveira, M ;

Mavoungou, DD ;

Wainberg, MA .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2000, 19 (10-12) :2019-2024

[9] Imidazole-based pinanamine derivatives: Discovery of dual inhibitors of the wild-type and drug-resistant mutant of the influenza A virus [J].

Dong, Jianghong ;

Chen, Shengwei ;

Li, Runfeng ;

Cui, Wei ;

Jiang, Haiming ;

Ling, Yixia ;

Yang, Zifeng ;

Hu, Wenhui .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 108 :605-615

[10] Green Synthesis and Molecular Docking of Thiazolyl-thiazole Derivatives as Potential Cytotoxic Agents [J].

Gomha, Sobhi M. ;

Abdelaziz, Mohamad R. ;

Abdel-Aziz, Hassan M. ;

Hassan, Shaimaa A. .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2017, 17 (09) :805-815

← 1 2 3 4 →