Journal ArticleDOI
In vitro anti-human immunodeficiency virus (HIV) activity of the chromanone derivative, 12-oxocalanolide A, a novel NNRTI
Ze-Qi Xu,Robert W. Buckheit,Tracy L. Stup,Michael T. Flavin,Albert Khilevich,John D. Rizzo,Lin Lin,David E. Zembower +7 more
TLDR
The three chromanone derivatives, (+)-, (-)-, and (+/-)-12-oxocalanolide A (2) are the first reported calanolide analogues capable of inhibiting SIV.About:
This article is published in Bioorganic & Medicinal Chemistry Letters.The article was published on 1998-08-18. It has received 42 citations till now. The article focuses on the topics: Lentivirus & Simian immunodeficiency virus.read more
Citations
More filters
Journal ArticleDOI
Recent progress in the development of coumarin derivatives as potent anti‐HIV agents
TL;DR: A dicamphanoyl‐khellactone analog, which was discovered and developed in the laboratory, and calanolide A are currently in preclinical studies and clinical trials, respectively.
Journal ArticleDOI
Structure-Activity Relationships of Synthetic Coumarins as HIV-1 Inhibitors
TL;DR: Recent progress in the discovery, structure modification, and structure-activity relationship studies of potent anti-HIV coumarin derivatives are described.
Journal ArticleDOI
Asymmetric Intramolecular Oxa‐Michael Addition of Activated α,β‐Unsaturated Ketones Catalyzed by a Chiral N,N′‐Dioxide Nickel(II) Complex: Highly Enantioselective Synthesis of Flavanones
Journal ArticleDOI
Asymmetric synthesis of fluorinated flavanone derivatives by an organocatalytic tandem intramolecular oxa-Michael addition/electrophilic fluorination reaction by using bifunctional cinchona alkaloids.
Journal ArticleDOI
Highly suppressing wild-type HIV-1 and Y181C mutant HIV-1 strains by 10-chloromethyl-11-demethyl-12-oxo-calanolide A with druggable profile.
Hai Xue,Xiaofan Lu,Purong Zheng,Li Liu,Chunyan Han,Jinping Hu,Zijie Liu,Tao Ma,Yan Li,Lin Wang,Zhiwei Chen,Gang Liu +11 more
TL;DR: In this paper, a new compound, 10-chloromethyl-11-demethyl-12-oxo-calanolide A (20, EC50 = 7.4 nM, SI = 1417), was reported.
References
More filters
Journal ArticleDOI
The calanolides, a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum.
Yoel Kashman,Kirk R. Gustafson,Richard W. Fuller,John H. Cardellina,James B. McMahon,Michael J. Currens,Robert W. Buckheit,Stephen H. Hughes,Gordon M. Cragg,Michael R. Boyd +9 more
TL;DR: Calanolide A was active not only against the AZT-resistant G-9106 strain of HIV-1 but also against the pyridinone-resistant A17 strain, which was of particular interest since the A17 virus is highly resistant to previously known HIV- 1 specific, non-nucleoside RT inhibitors.
Journal ArticleDOI
The inophyllums, novel inhibitors of HIV-1 reverse transcriptase isolated from the Malaysian tree, Calophyllum inophyllum Linn
A D Patil,A J Freyer,D. S. Eggleston,R C Haltiwanger,M F Bean,P B Taylor,M J Caranfa,A L Breen,H R Bartus,Randall K. Johnson +9 more
TL;DR: As part of a search for novel inhibitors of HIV-1 reverse transcriptase, the acetone extract of the giant African snail, Achatina fulica, was shown to be active and 11 compounds of the inophyllum class were isolated, indicating certain structural requirements in the chromanol ring.
Journal ArticleDOI
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers
Michael T. Flavin,John D. Rizzo,Albert Khilevich,Alla Kucherenko,Abram Kivovich Sheinkman,Vilayphone Vilaychack,Lin Lin,Wei Chen,Eugenia Mata Greenwood,Thitima Pengsuparp,John M. Pezzuto,Stephen H. Hughes,Thomas M. Flavin,Michael Cibulski,William A. Boulanger,Robert L. Shone,Ze-Qi Xu +16 more
TL;DR: The anti-HIV agent (+/-)-calanolide A (1) has been synthesized in a five-step approach starting with phloroglucinol, which includes Pechmann reaction, Friedel-Crafts acylation, chromenylation with 4,4-dimethoxy- 2-methylbutan-2-ol, cyclization, and Luche reduction.
Journal ArticleDOI
Analysis of nonnucleoside drug-resistant variants of human immunodeficiency virus type 1 reverse transcriptase
TL;DR: Analysis of mutants used to analyze calanolide A, 1H,3H-thiazolo[3,4-a]benzimidazole(4i), and the acyclic nucleoside analog 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine suggest that all three drugs interact with HIV-1 RT within the previously defined common binding site for nonnucleoside inhibitors.
Journal ArticleDOI
Biological and biochemical anti-HIV activity of the benzothiadiazine class of nonnucleoside reverse transcriptase inhibitors.
Robert W. Buckheit,Valerie Fliakas-Boltz,W. Don Decker,Joseph L. Roberson,Cathi A. Pyle,E. Lucile White,Bonnie J. Bowdon,James B. McMahon,Michael R. Boyd,John P. Bader,David G. Nickell,Hubert Barth,Tammy Antonucci +12 more
TL;DR: The benzothiadiazine class of compounds represents a new active anti-HIV-1 chemotype within the diverse group of nonnucleoside reverse transcriptase inhibitors.