The anti-HIV potential of imidazole, oxazole and thiazole hybrids: A mini-review

被引:27
作者
Deng, Cui [1 ,2 ]
Yan, Heng [3 ]
Wang, Jun [1 ,2 ]
Liu, Bao-shan [1 ,2 ]
Liu, Kai [1 ,2 ]
Shi, Yu-min [1 ,2 ]
机构
[1] Hubei Univ Sci & Technol, Hubei Engn Res Ctr Fragrant Plants, Xianning 437100, Hubei, Peoples R China
[2] Xianning Res Acad Ind Technol Osmanthus fragrans, Xianning 437100, Hubei, Peoples R China
[3] Hubei Prov Inst Food Supervis & Test, Wuhan 430070, Hubei, Peoples R China
关键词
Acquired immune deficiency syndrome; Human immunodeficiency virus; Imidazole; Oxazole; Thiazole; Hybrid molecules; REVERSE-TRANSCRIPTASE INHIBITORS; ANTIPROLIFERATIVE ACTIVITY; BIOLOGICAL EVALUATION; MOLECULAR DOCKING; CRYSTAL-STRUCTURE; WILD-TYPE; IN-VITRO; DERIVATIVES; DESIGN; OPTIMIZATION;
D O I
10.1016/j.arabjc.2022.104242
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Human immunodeficiency virus (HIV) especially HIV-1 infection and its progression to acquired immune deficiency syndrome (AIDS) remains a significant global health challenge. The advent of the highly active antiretroviral therapy (HAART) has greatly extended the life expectancy of patients living with HIV, but it has become evident that long-term HAART will not eliminate the HIV reservoir and cure the infection. Moreover, the drug resistance and undesirable side effects hamper efficacious therapy, creating an urgent need to develop novel, more effective and less toxic anti-HIV therapeutics. Imidazole, oxazole and thiazole with two heteroatoms at meta-position of five-membered rings are fascinating structures and constitute an important class of heterocycles in drug discovery. Their derivatives could exert the anti-HIV activity through diverse mechanisms and possess promising antiviral activity against both drug-sensitive and drug-resistant HIV strains. This review summarizes the research progress made regarding the anti-HIV potential of imidazole, oxazole and thiazole hybrids, and the structure-activity relationships (SARs) are also discussed to facilitate further rational design of more effective candidates, covering articles published from 2012 to 2022.(c) 2022 The Author(s). Published by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
引用
收藏
页数:16
相关论文
共 98 条
[71]   Studies towards the Design and Synthesis of Novel 1,5-Diaryl-1H-imidazole-4-carboxylic Acids and 1,5-Diaryl-1H-imidazole-4-carbohydrazides as Host LEDGF/p75 and HIV-1 Integrase Interaction Inhibitors [J].
Rashamuse, Thompho J. ;
Fish, Muhammad Q. ;
Coyanis, E. Mabel ;
Bode, Moira L. .
MOLECULES, 2021, 26 (20)
[72]   Design, synthesis and biological evaluation of novel 2-(5-aryl-1H-imidazol-1-yl) derivatives as potential inhibitors of the HIV-1 Vpu and host BST-2 protein interaction [J].
Rashamuse, Thompho J. ;
Njengele, Zikhona ;
Coyanis, E. Mabel ;
Sayed, Yasien ;
Mosebi, Salerwe ;
Bode, Moira L. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2020, 190
[73]   Oxazole-Benzenesulfonamide Derivatives Inhibit HIV-1 Reverse Transcriptase Interaction with Cellular eEF1A and Reduce Viral Replication [J].
Rawle, Daniel J. ;
Li, Dongsheng ;
Wu, Zhonglan ;
Wang, Lu ;
Choong, Marcus ;
Lor, Mary ;
Reid, Robert C. ;
Fairlie, David P. ;
Harris, Jonathan ;
Tachedjian, Gilda ;
Poulsen, Sally-Ann ;
Harrich, David .
JOURNAL OF VIROLOGY, 2019, 93 (12)
[74]   Inhibitors of Human Immunodeficiency Virus Type 1 (HIV-1) Attachment. 12. Structure-Activity Relationships Associated with 4-Fluoro-6-azaindole Derivatives Leading to the Identification of 1-(4-Benzoylpiperazin-1-yl)-2-(4-fluoro-7-[1,2,3]triazol-1-yl-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione (BMS-585248) [J].
Regueiro-Ren, Alicia ;
Xue, Qiufen M. ;
Swidorski, Jacob J. ;
Gong, Yi-Fei ;
Mathew, Marina ;
Parker, Dawn D. ;
Yang, Zheng ;
Eggers, Betsy ;
D'Arienzo, Celia ;
Sun, Yongnian ;
Malinowski, Jacek ;
Gao, Qi ;
Wu, Dedong ;
Langley, David R. ;
Colonno, Richard J. ;
Chien, Caly ;
Grasela, Dennis M. ;
Zheng, Ming ;
Lin, Pin-Fang ;
Meanwell, Nicholas A. ;
Kadow, John F. .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (04) :1656-1669
[75]   Design, synthesis, and docking studies of new 2-benzoxazolinone derivatives as anti-HIV-1 agents [J].
Safakish, Mahdieh ;
Hajimahdi, Zahra ;
Zabihollahi, Rezvan ;
Aghasadeghi, Mohammad R. ;
Vahabpour, Rouhoullah ;
Zarghi, Afshin .
MEDICINAL CHEMISTRY RESEARCH, 2017, 26 (11) :2718-2726
[76]   Design, Synthesis and Characterization of HIV-1 CA-Targeting Small Molecules: Conformational Restriction of PF74 [J].
Sahani, Rajkumar Lalji ;
Diana-Rivero, Raquel ;
Vernekar, Sanjeev Kumar V. ;
Wang, Lei ;
Du, Haijuan ;
Zhang, Huanchun ;
Castaner, Andres Emanuelli ;
Casey, Mary C. ;
Kirby, Karen A. ;
Tedbury, Philip R. ;
Xie, Jiashu ;
Sarafianos, Stefan G. ;
Wang, Zhengqiang .
VIRUSES-BASEL, 2021, 13 (03)
[77]   Discovery of a novel 5-carbonyl-1H-imidazole-4-carboxamide class of inhibitors of the HIV-1 integrase-LEDGF/p75 interaction [J].
Serrao, Erik ;
Xu, Zhong-Liang ;
Debnath, Bikash ;
Christ, Frauke ;
Debyser, Zeger ;
Long, Ya-Qiu ;
Neamati, Nouri .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (19) :5963-5972
[78]   Pyridine-Substituted Desoxyritonavir Is a More Potent Inhibitor of Cytochrome P450 3A4 than Ritonavir [J].
Sevrioukova, Irina F. ;
Poulos, Thomas L. .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (09) :3733-3741
[79]   Imidazole: An Essential Edifice for the Identification of New Lead Compounds and Drug Development [J].
Shalmali, Nishtha ;
Ali, Md. Rahmat ;
Bawa, Sandhya .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2018, 18 (02) :142-163
[80]   Synthesis, anti-HIV-1 and antiproliferative evaluation of novel 4-nitroimidazole derivatives combined with 5-hydroxy-4-pyridinone moiety [J].
Shirvani, Pouria ;
Fassihi, Afshin ;
Saghaie, Lotfollah ;
Van Belle, Siska ;
Debyser, Zeger ;
Christ, Frauke .
JOURNAL OF MOLECULAR STRUCTURE, 2020, 1202