ArticleJournal of medicinal chemistry2009
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.
Article in Journal of medicinal chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 73 citations in OpenAlex.
- Synthesis ofMagnetic resonance in chemistry : MRC · 2026Article
- Design, synthesis, and structure activity relationship analysis of new betulinic acid derivatives as potent HIV inhibitors.European journal of medicinal chemistry · 2021Article
- Recent advances in natural anti-HIV triterpenoids and analogs.Medicinal research reviews · 2020Review
- New Phosphorus Analogs of Bevirimat: Synthesis, Evaluation of Anti-HIV-1 Activity and Molecular Docking Study.International journal of molecular sciences · 2019Article
- Promiscuous, Multi-Target Lupane-Type Triterpenoids Inhibits Wild Type and Drug Resistant HIV-1 Replication Through the Interference With Several Targets.Frontiers in pharmacology · 2018Article
- Betulinic Acid Induces Apoptosis in Differentiated PC12 Cells Via ROS-Mediated Mitochondrial Pathway.Neurochemical research · 2017Article
- Incorporation of Privileged Structures into Bevirimat Can Improve Activity against Wild-Type and Bevirimat-Resistant HIV-1.Journal of medicinal chemistry · 2016Article
- Fluorinated betulinic acid derivatives and evaluation of their anti-HIV activity.Bioorganic & medicinal chemistry letters · 2016Article
- A-ring modified betulinic acid derivatives as potent cancer preventive agents.Bioorganic & medicinal chemistry letters · 2014Article
- Article
- Anti-AIDS agents 90. novel C-28 modified bevirimat analogues as potent HIV maturation inhibitors.Journal of medicinal chemistry · 2012Article
- Inhibitory effect of aqueous Dandelion extract on HIV-1 replication and reverse transcriptase activity.BMC complementary and alternative medicine · 2011Article
- New betulinic acid derivatives as potent proteasome inhibitors.Bioorganic & medicinal chemistry letters · 2011Article
- Synthesis of new 2'-deoxy-2'-fluoro-4'-azido nucleoside analogues as potent anti-HIV agents.European journal of medicinal chemistry · 2011Article
- Understanding the structure-activity relationship of betulinic acid derivatives as anti-HIV-1 agents by using 3D-QSAR and docking.Journal of molecular modeling · 2011Article
- Modern natural products drug discovery and its relevance to biodiversity conservation.Journal of natural products · 2011Review
- Efficient synthesis and biological evaluation of epiceanothic acid and related compounds.Bioorganic & medicinal chemistry letters · 2011Article
- Conjugates of betulin derivatives with AZT as potent anti-HIV agents.Bioorganic & medicinal chemistry · 2010Article
- Screening of filamentous fungi to identify biocatalysts for lupeol biotransformation.Molecules (Basel, Switzerland) · 2010Article
- Synthesis and anti-HIV activity of 2'-deoxy-2'-fluoro-4'-C-ethynyl nucleoside analogs.Bioorganic & medicinal chemistry letters · 2010Article
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Authors and funding
10 authors at 1 institution in 1 country.
Funding
Abstract
In a continuing study of potent anti-HIV agents, seventeen 28,30-disubstituted betulinic acid (BA, 1) derivatives and seven novel 3,28-disubstituted BA analogues were designed, synthesized, and evaluated for in vitro antiviral activity. Among them, compound 21 showed an improved solubility and equal anti-HIV potency (EC(50) = 0.09 microM) when compared to HIV entry inhibitors 3b (IC9564, (3R,4S)-N'-[N-[3beta-hydroxy-lup-20(29)-en-28-oyl]-8-aminooctanoyl]-4-amino-3-hydroxy-6-methylheptanoic acid) and 4 (A43-D, [[N-[3beta-O-(3',3'-dimethylsuccinyl)-lup-20(29)-en-28-oyl]-7-aminoheptyl]carbamoyl]methane). Using a cyclic secondary amine to form the C-28 amide bond increased the metabolic stability of the derivatives significantly in pooled human liver microsomes. The most potent compounds 47 and 48 displayed potent anti-HIV activity with EC(50) values of 0.007 and 0.006 microM, respectively. These results are slightly better than that of bevirimat (2, 3',3'-dimethylsuccinylbetulinic acid), which is currently in phase IIb clinical trials. Compounds 47 and 48 should serve as attractive promising leads to develop next generation, metabolically stable, 3,28-disubstituted bifunctional HIV-1 inhibitors as clinical trials candidates.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.