Synthesis of dual 14C-labeled (+)-calanolide A, a naturally occurring anti-HIV agent

Gaddam, Subbareddy; Khilevich, Albert; Filer, Crist N.; Rizzo, John D.; Giltner, Jeremey; Flavin, Michael T.; Xu, Zhenghu

doi:10.1002/(sici)1099-1344(199711)39:11<901::aid-jlcr39>3.0.co;2-h

Cited by 9 publications

(8 citation statements)

References 11 publications

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“…The author has pointed out that the specific rotation of the synthetic ( S )-2,6-dimethylchroman-4-one was higher than that for the natural product. The intermediates 2-methyl- and 2,3-dimethylchromanones required for (+)-calanolide A, an anti-HIV agent, were prepared by a Mitsunobu intramolecular cyclization. − Other applications leading to six-membered heterocycles involve (i) heliquinomycinone reported by Danishefsky and co-workers, (ii) functionalized steroid-like molecules reported by Yus and co-workers, and (iii) the structural elucidation of capituloside reported by Zhou and co-workers…”

Section: Phenols and Alcohols As Nucleophiles: Ether Formationmentioning

confidence: 99%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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His research interests include Organophosphorus Chemistry and Main Group Chemistry. He has over 115 publications so far and is a fellow of the Indian Academy of Sciences, Bangalore. N. N. Bhuvan Kumar was born in Cherukupalli, Guntur, India. After completing his B.Sc. from Nagarjuna University, he joined the School of Chemistry, University of Hyderabad, as a postgraduate student in the year 2000 and obtained his Master's degree in Chemistry. Currently, he is pursuing a Ph.D. on Organophosphonates under the supervision of Prof. K. C. Kumara Swamy. E. Balaraman was born in Kancheepuram, Chennai, India, in 1980. He received his M.Sc. in Chemistry from Vivekananda College [Madras University (2002)] and his Ph.D. degree in the areas of organophosphonates and modified BINOLs under the guidance of Prof. K. C. Kumara Swamy. Presently he is a postdoctoral fellow with Professors David Milstein and Ronny Neumann at the Weizmann Institute of Science, Israel. K. V. P. Pavan Kumar was born in Hyderabad (Andhra Pradesh), India, in 1979. He obtained his B.Sc. (Chemistry Honors) and M.Sc. (Chemistry) degrees from Sri Sathya Sai Institute of Higher Learning, Puttaparthi, A.P., India. He obtained his Ph.D. degree under the guidance of Prof. K. C. Kumara Swamy in October 2006. Presently he is working as a postdoctoral fellow in the area of hydroamination reactions using new titanium catalysts with Prof. Pierre Le Gendre at the Universite ´de Bourgogne, France.

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Section: Phenols and Alcohols As Nucleophiles: Ether Formationmentioning

confidence: 99%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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“…The synthesis of calanolide A has been reported in [21,42,53] and the synthesis of the isomers of calanolide A has been reported [18,32].…”

Section: Calanolide Synthetic Analogsmentioning

confidence: 99%

Coumarins as Inhibitors of HIV Reverse Transcriptase

Kostova

2006

CHR

146

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Acquired immunodeficiency syndrome (AIDS), a degenerative disease of the immune and central nervous systems, is an enormous world-wide health threat. No cure has been found, and research is aimed at developing chemotherapy against the causative agent, human immunodeficiency virus (HIV). Chemotherapy for AIDS has progressed steadily in the past decade. However, new, effective, and less toxic chemotherapeutic agents are still needed. Plants, particularly anti-infective or immunomodulating herbal medicines, can serve as sources of new active leads to be further developed as anti-AIDS drug candidates. A lot of structurally different natural coumarins were found to display potent anti-HIV activity and continued progress is anticipated in the discovery of new leads and in the development of these agents as potential anti-AIDS drug candidates. Recent studies based on the account of various coumarins from plant sources and their analogs--synthetic coumarins, indicate that some of them serve as potent nonnucleoside RT-inhibitors, another as inhibitors of HIV-integrase or HIV-protease. The current review demonstrates the variety of coumarins of natural plant origin and synthetic coumarins having unique mechanism of action to one of the most important stage of HIV replication (RT-inhibition). The merits of selecting potential anti-HIV agents to be used in rational combination drugs design and structure-activity relationships are discussed. The scientific community is looking actively for new drugs and combinations for treatment of HIV infection effective for first-line treatment, as well as against drug-resistant mutants.

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“…Hard and borderline nucleophiles exclusively substituted chlorine in position 4, while soft nucleophiles substituted the group in position 3. Chromene-2-one derivatives have been reported for anticoagulant [3][4][5] , antibacterial [6][7] , antiinflamatory 8 , antimicrobial 9 , antiHIV [10][11][12][13] , antioxidant 14 , anticancer 15 and antiproliferative and antiviral 16 activities. It was found that when one biodynamic heterocyclic system was coupled with another heterocyclic system, enhanced biological activity was produced.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Microbiological Activity of Some Newly Synthesized Derivatives of 2‐Oxo‐2H‐chromen‐2‐one

Daci-Ajvazi¹,

Govori²,

Omeragiq³

2010

Journal of Chemistry

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By the action of 2-amino-5-methylthio-1,3,4-thiadiazole, 3-amino-5-methylisoxazole, 2-amino-6-fluorobenzothiazole, 2-amino-5-chloropyridine, respectively, on 4-chloro-2-oxo-2H-chromene-3-sulfonyl chloride, the corresponding 9-methylthio-7,7-dioxo-7,7a-dihydro-5-oxo-7λ6,10-dithia-8,11-diaza-cyclopenta[b] phenantren-6-one, 9-methyl-7,7-dioxo-7H-5,8-dioxa-7λ6-thia-7a,11-diaza-cyclopenta[b] phenantren-6-one, 9-fluoro-7,7-dioxo-7H-5-oxa-7λ6,12-dithia-7a,13-diaza-indeno[1,2-b] phenantren-6-one and 9-Chloro-7,7-dioxo-7H-5-oxa-7λ6-thia-7a,12-diaza-benzo[α]anthracen -6-one were formed and they have been isolated in satisfying yields. Based on the biological activity of chromene-2-ones and heterocyclic compounds condensed in position 3 and 4, we also studied microbiological activity of these new compounds(5-8), againstStaphylococcus aureusATCC 25923,Streptococcus pneumoniae, Aeromonas Salmonicida, Bacillus sppand some of them exhibited significant activity.

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Synthesis of dual 14C-labeled (+)-calanolide A, a naturally occurring anti-HIV agent

Cited by 9 publications

References 11 publications

Mitsunobu and Related Reactions: Advances and Applications

Mitsunobu and Related Reactions: Advances and Applications

Coumarins as Inhibitors of HIV Reverse Transcriptase

Synthesis and Microbiological Activity of Some Newly Synthesized Derivatives of 2‐Oxo‐2H‐chromen‐2‐one

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