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Cited by 53HIV/AIDS drug development and treatmentHIV Research and TreatmentSynthesis of Tetrazole Derivatives

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Design, Synthesis, and Biological Evaluation of Novel Hybrid Dicaffeoyltartaric/Diketo Acid and Tetrazole-Substituted l-Chicoric Acid Analogue Inhibitors of Human Immunodeficiency Virus Type 1 Integrase

Crosby, David C., Lei, Xiangyang, Gibbs, Charles G., McDougall, Brenda R., Robinson, W. Edward, Reinecke, Manfred G.·2010·Journal of Medicinal Chemistry
DOI 10.1021/jm1010594
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Abstract

Fourteen analogues of the anti-HIV-1 integrase (IN) inhibitor L-chicoric acid (L-CA) were prepared. Their IC(50) values for 3'-end processing and strand transfer against recombinant HIV-1 IN were determined in vitro, and their cell toxicities and EC(50) against HIV-1 were measured in cells (ex vivo). Compounds 1-6 are catechol/β-diketoacid hybrids, the majority of which exhibit submicromolar potency against 3'-end processing and strand transfer, though only with modest antiviral activities. Compounds 7-10 are L-CA/p-fluorobenzylpyrroloyl hybrids, several of which were more potent against strand transfer than 3'-end processing, a phenomenon previously attributed to the β-diketo acid pharmacophore. Compounds 11-14 are tetrazole bioisosteres of L-CA and its analogues, whose in vitro potencies were comparable to L-CA but with enhanced antiviral potency. The trihydroxyphenyl analogue 14 was 30-fold more potent than L-CA at relatively nontoxic concentrations. These data indicate that L-CA analogues are attractive candidates for development into clinically relevant inhibitors of HIV-1 IN.

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Metadata

Authors
Crosby, D. C., Lei, X., Gibbs, C. G., McDougall, B. R., Robinson, W. E., & Reinecke, M. G.
Affiliations
  • Department of Pathology and Laboratory Medicine
  • Texas Christian University (US)
Corresponding author
Reinecke, Manfred G.
ORCID
Venue
Journal of Medicinal Chemistry
Publisher
American Chemical Society (ACS)
Published
2010-10-26
Volume
53
Issue
22
Pages
8161-8175
ISSN
  • 0022-2623 (ISSN-L)
  • 1520-4804
DOI
10.1021/jm1010594
OpenAlex
W2331728824
Cited by
53
References
3
Citations by year
2026: 3 · 2025: 5 · 2024: 1 · 2023: 1 · 2022: 3 · 2021: 3 · 2020: 3 · 2019: 7 · 2018: 5 · 2017: 3 · 2016: 3 · 2015: 2 · 2014: 3 · 2013: 3 · 2012: 4
FWCI
2.28
Type
journal article
Language
en
Open access
closed
Locations
  • Journal of Medicinal Chemistry (publishedVersion)
  • PubMed (publishedVersion)
Funders
  • U.S. Public Health Service (5R0IAI063973)
  • National Institute of Allergy and Infectious Diseases (R21AI054305)
Topics
  • Health Sciences › Medicine › Infectious Diseases › HIV/AIDS drug development and treatment
  • Life Sciences › Immunology and Microbiology › Virology › HIV Research and Treatment
  • Physical Sciences › Chemistry › Organic Chemistry › Synthesis of Tetrazole Derivatives
Keywords
HIV-1 integrase inhibitors, 3' end processing, strand transfer, antiviral activity, cytotoxicity, pharmacophore
MeSH terms
Caffeic Acids, Cell Line, Humans, Keto Acids, Structure-Activity Relationship, Succinates, Tetrazoles, Virology, HIV-1, HIV Integrase, HIV Integrase Inhibitors

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