Literature DB >> 27676157

Incorporation of Privileged Structures into Bevirimat Can Improve Activity against Wild-Type and Bevirimat-Resistant HIV-1.

Yu Zhao1, Qiong Gu1,2, Susan L Morris-Natschke1, Chin-Ho Chen3, Kuo-Hsiung Lee1,4.   

Abstract

Two "privileged fragments", caffeic acid and piperazine, were integrated into bevirimat producing new derivatives with improved activity against HIV-1/NL4-3 and NL4-3/V370A carrying the most prevalent bevirimat-resistant polymorphism. The activity of one of these, 18c, was increased by 3-fold against NL4-3 and 51-fold against NL4-3/V370A. Moreover, 18c is a maturation inhibitor with improved metabolic stability. Our study suggested that integration of privileged motifs into promising natural product skeletons is an effective strategy for discovering potent derivatives.

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Year:  2016        PMID： 27676157      PMCID： PMC5151175          DOI： 10.1021/acs.jmedchem.6b00461

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  32 in total

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Review 3.  Anti-HIV activities of natural antioxidant caffeic acid derivatives: toward an antiviral supplementation diet.

Authors:  Fabrice Bailly; Philippe Cotelle
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6.  Alkyl Amine Bevirimat Derivatives Are Potent and Broadly Active HIV-1 Maturation Inhibitors.

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Journal:  Antimicrob Agents Chemother       Date:  2015-10-19       Impact factor: 5.191

7.  Piperazine-based CCR5 antagonists as HIV-1 inhibitors. IV. Discovery of 1-[(4,6-dimethyl-5-pyrimidinyl)carbonyl]- 4-[4-[2-methoxy-1(R)-4-(trifluoromethyl)phenyl]ethyl-3(S)-methyl-1-piperazinyl]- 4-methylpiperidine (Sch-417690/Sch-D), a potent, highly selective, and orally bioavailable CCR5 antagonist.

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Journal:  J Med Chem       Date:  2004-05-06       Impact factor: 7.446

8.  Reaction of rosmarinic acid with nitrite ions in acidic conditions: discovery of nitro- and dinitrorosmarinic acids as new anti-HIV-1 agents.

Authors:  Mélanie Dubois; Fabrice Bailly; Gladys Mbemba; Jean-François Mouscadet; Zeger Debyser; Myriam Witvrouw; Philippe Cotelle
Journal:  J Med Chem       Date:  2008-03-20       Impact factor: 7.446

9.  Anti-AIDS agents. 78. Design, synthesis, metabolic stability assessment, and antiviral evaluation of novel betulinic acid derivatives as potent anti-human immunodeficiency virus (HIV) agents.

Authors:  Keduo Qian; Donglei Yu; Chin-Ho Chen; Li Huang; Susan L Morris-Natschke; Theodore J Nitz; Karl Salzwedel; Mary Reddick; Graham P Allaway; Kuo-Hsiung Lee
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Journal:  Open Med Chem J       Date:  2014-09-03
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  11 in total

1.  MicroED structures of HIV-1 Gag CTD-SP1 reveal binding interactions with the maturation inhibitor bevirimat.

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Journal:  Proc Natl Acad Sci U S A       Date:  2018-12-10       Impact factor: 11.205

2.  A Maldiisotopic Approach to Discover Natural Products: Cryptomaldamide, a Hybrid Tripeptide from the Marine Cyanobacterium Moorea producens.

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Journal:  J Nat Prod       Date:  2017-04-27       Impact factor: 4.050

Review 3.  Recent advances in natural anti-HIV triterpenoids and analogs.

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Journal:  Med Res Rev       Date:  2020-07-14       Impact factor: 12.944

4.  Preservation of HIV-1 Gag Helical Bundle Symmetry by Bevirimat Is Central to Maturation Inhibition.

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Review 5.  Structure and Anti-HIV Activity of Betulinic Acid Analogues.

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6.  Discovery and synthesis of novel beesioside I derivatives with potent anti-HIV activity.

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Journal:  Eur J Med Chem       Date:  2021-02-14       Impact factor: 6.514

9.  Application of the Triazolization Reaction to Afford Dihydroartemisinin Derivatives with Anti-HIV Activity.

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10.  Promiscuous, Multi-Target Lupane-Type Triterpenoids Inhibits Wild Type and Drug Resistant HIV-1 Replication Through the Interference With Several Targets.

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Journal:  Front Pharmacol       Date:  2018-04-18       Impact factor: 5.810
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