Journal ArticleDOI
Novel approach for synthesis of (±)-calanolide a and its anti-HIV activity
Alla Kucherenko,Michael T. Flavin,William A. Boulanger,Albert Khilevich,Robert L. Shone,John D. Rizzo,Abram Kivovich Sheinkman,Ze-Qi Xu +7 more
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The key intermediate, chromene 5, was synthesized by the sequence of Pechmann reaction, acylation and chromenylation by 4,4-dimethoxy-2-methylbutan- 2-ol.About:
This article is published in Tetrahedron Letters.The article was published on 1995-07-31. It has received 44 citations till now. The article focuses on the topics: Calanolide A.read more
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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
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
Chemical Library and Structure–Activity Relationships of 11-Demethyl-12-oxo Calanolide A Analogues as Anti-HIV-1 Agents
TL;DR: A novel compound (10-bromomethyl-11-demethyl-12-oxo calanolide A, 123) was identified to have much higher inhibitory potency and therapeutic index than those of the class compound against HIV-1.
Journal ArticleDOI
Synthesis of Coumarins in a Molten n‐Bu4NOAc/n‐Bu4NBr Mixture through a Domino Heck Reaction/Cyclization Process
TL;DR: In this paper, 4-Arylcoumarins can be prepared in good to high yields by reacting readily available methyl or butyl 3-(o-hydroxyaryl)acrylates with aryl iodides and bromides.
Journal ArticleDOI
Synthesis of (+)-calanolide A, an anti-HIV agent, Via enzyme-catalyzed resolution of the aldol products
Albert Khilevich,Aye Aye Mar,Michael T. Flavin,John D. Rizzo,Lin Lin,S. Dzekhtser,D. Brankovic,Heping Zhang,Wei Chen,Shuyuan Liao,David E. Zembower,Ze-Qi Xu +11 more
TL;DR: The synthesis of (+)-calanolide A, an anti-HIV-1 agent, is described, which was resolved by a lipase-catalyzed acylation reaction of compound 2 stereoselectively produced the desired syn diastereomer.
References
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Journal ArticleDOI
Lanthanoids in organic synthesis. 6. Reduction of .alpha.-enones by sodium borohydride in the presence of lanthanoid chlorides: synthetic and mechanistic aspects
Andre L. Gemal,Jean Louis Luche +1 more
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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
Reconstruction and future trends of the AIDS epidemic in the United States
TL;DR: Although the overall HIV infection rate in the United States has declined, the demands on the U.S. health care system for treatment and care of HIV-infected individuals remain enormous.
Journal ArticleDOI
Brief report: primary infection with zidovudine-resistant human immunodeficiency virus type 1.
Alejo Erice,Douglas L. Mayers,David G. Strike,Kim J. Sannerud,Francine E. McCutchan,Keith Henry,Henry H. Balfour +6 more
TL;DR: A patient with symptomatic HIV-1 infection who had primary infection with a virus resistant to zidovudine is described, according to both phenotypic and genotypic analyses.