ArticleBioorganic & medicinal chemistry letters2012
Synthesis of betulinic acid derivatives as entry inhibitors against HIV-1 and bevirimat-resistant HIV-1 variants.
Article in Bioorganic & medicinal chemistry letters, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 36 citations in OpenAlex.
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- In Vitro Anti-HIV-1 Activity of Chitosan OligomersBiotech (Basel (Switzerland)) · 2023Article
- New triazole-substituted triterpene derivatives exhibiting anti-RSV activity: synthesis, biological evaluation, and molecular modeling.Beilstein journal of organic chemistry · 2022Article
- Application of Amino Acids in the Structural Modification of Natural Products: A Review.Frontiers in chemistry · 2021Review
- Recent advances in natural anti-HIV triterpenoids and analogs.Medicinal research reviews · 2020Review
- HIV-1 Maturation: Lessons Learned from Inhibitors.Viruses · 2020Review
- New Phosphorus Analogs of Bevirimat: Synthesis, Evaluation of Anti-HIV-1 Activity and Molecular Docking Study.International journal of molecular sciences · 2019Article
- Reviewing HIV-1 Gag Mutations in Protease Inhibitors Resistance: Insights for Possible Novel Gag Inhibitor Designs.Molecules (Basel, Switzerland) · 2019Review
- Structure and Anti-HIV Activity of Betulinic Acid Analogues.Current medical science · 2018Review
- Insights into the activity of maturation inhibitor PF-46396 on HIV-1 clade C.Scientific reports · 2017Article
- Structure-Activity Relationships of the Human Immunodeficiency Virus Type 1 Maturation Inhibitor PF-46396.Journal of virology · 2016Article
- Molecular cloning and promoter analysis of squalene synthase and squalene epoxidase genes from Betula platyphylla.Protoplasma · 2016Article
- Identification of potent maturation inhibitors against HIV-1 clade C.Scientific reports · 2016Article
- Aloperine and Its Derivatives as a New Class of HIV-1 Entry Inhibitors.ACS medicinal chemistry letters · 2016Article
- Alkyl Amine Bevirimat Derivatives Are Potent and Broadly Active HIV-1 Maturation Inhibitors.Antimicrobial agents and chemotherapy · 2016Article
- HIV-1 Gag as an Antiviral Target: Development of Assembly and Maturation Inhibitors.Current topics in medicinal chemistry · 2016Review
- HIV-1 gag: an emerging target for antiretroviral therapy.Current topics in microbiology and immunology · 2015Review
- Dolabelladienols A-C, new diterpenes isolated from Brazilian brown alga Dictyota pfaffii.Marine drugs · 2014Article
- New betulinic acid derivatives for bevirimat-resistant human immunodeficiency virus type-1.Journal of medicinal chemistry · 2013Article
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
Abstract
Betulinic acid derivatives modified at the C28 position are HIV-1entry inhibitors such as compound A43D; however, modified at the C3 position instead of C28 give HIV-1 maturation inhibitor such as bevirimat. Bevirimat exhibited promising pharmacokinetic profiles in clinical trials, but its effectiveness was compromised by the high baseline drug resistance of HIV-1 variants with polymorphism in the putative drug binding site. In an effort to determine whether the viruses with bevirimat resistant polymorphism also altered their sensitivities to the betulinic acid derivatives that inhibit HIV-1 entry, a series of new betulinic acid entry inhibitors were synthesized and tested for their activities against HIV-1 NL4-3 and NL4-3 variants resistant to bevirimat. The results show that the bevirimat resistant viruses were approximately 5- to10-fold more sensitive to three new glutamine ester derivatives (13, 15 and 38) and A43D in an HIV-1 multi-cycle replication assay. In contrast, the wild type NL4-3 and the bevirimat resistant variants were equally sensitive to the HIV-1 RT inhibitor AZT. In addition, these three new compounds markedly improved microsomal stability compared to A43D.
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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.