Total Synthesis of (±)-Calanolide A

Rehder, Ken S.; Kepler, John A.

doi:10.1080/00397919608003823

Cited by 20 publications

(16 citation statements)

References 13 publications

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“…Disubstituted DCK analogs were also synthesized and screened for inhibition of HIV replication in H9 lymphocytes (Table I). 26 4-Methyl-5-methoxy DCK (70) was the most promising compound and was as active as 4-methyl DCK (52) and much better than DCK and AZT in the same assay. Dimethyl DCK analogs 63-66 were more potent than AZT but less potent than DCK.…”

Section: Substituents On Coumarin Skeletonmentioning

confidence: 99%

“…50 Compound 101 is synthesized from phloroglucinol in five steps and is being investigated for clinical research. [51][52][53][54] A phase IA studies showed that 101 was generally well tolerated in doses up to 600 mg. In human subjects, plasma levels of 101 were higher than those predicted from animal studies.…”

Section: E In Vitro and In Vivo Study Of Calanolidesmentioning

confidence: 99%

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Recent progress in the development of coumarin derivatives as potent anti‐HIV agents

Suzuki

Xie

et al. 2003

Medicinal Research Reviews

487

213

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Numerous plant-derived compounds have been evaluated for inhibitory effects against HIV replication, and some coumarins have been found to inhibit different stages in the HIV replication cycle. This review article describes recent progress in the discovery, structure modification, and structure-activity relationship studies of potent anti-HIV coumarin derivatives. A dicamphanoyl-khellactone (DCK) analog, which was discovered and developed in our laboratory, and calanolide A are currently in preclinical studies and clinical trials, respectively.

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Section: Substituents On Coumarin Skeletonmentioning

confidence: 99%

Section: E In Vitro and In Vivo Study Of Calanolidesmentioning

confidence: 99%

Recent progress in the development of coumarin derivatives as potent anti‐HIV agents

Suzuki

Xie

et al. 2003

Medicinal Research Reviews

487

213

View full text Add to dashboard Cite

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“…The anti-HIV agent (+/−)-calanolide A has been synthesized [5–7] 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. Cyclization of chromene to chromanon was achieved by employing either acetaldehyde diethyl acetal or paraldehyde in the presence of trifluoroacetic acid and pyridine or PPTS.…”

Section: Introductionmentioning

confidence: 99%

Structure‐Activity Relationships of Synthetic Coumarins as HIV‐1 Inhibitors

Kostova¹,

Raleva

Genova

et al. 2006

Bioinorganic Chemistry and Applications

133

104

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HIV/AIDS pandemics is a serious threat to health and development of mankind, and searching for effective anti-HIV agents remains actual. Considerable progress has been made in recent years in the field of drug development against HIV. A lot of structurally different coumarins were found to display potent anti-HIV activity. The current review demonstrates the variety of synthetic coumarins having unique mechanism of action referring to the different stages of HIV replication. Recent studies based on the account of various synthetic coumarins seem to indicate that some of them serve as potent non-nucleoside RT-inhibitors, another as inhibitors of HIV-integrase or HIV-protease. 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 resistant mutants. The investigation on chemical anti-HIV agents gives hope and optimism about it. This review article describes recent progress in the discovery, structure modification, and structure-activity relationship studies of potent anti-HIV coumarin derivatives.

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“…The anti-HIV agent (+/-)-calanolide A has been synthesized [38,56,85] in a five-step approach, which includes Pechmann reaction, Friedel-Crafts acylation, chromenylation with 4,4-dimethoxy-2-methylbutan-2-ol, cyclization, and Luche reduction. Cyclization of chromene to chromanon was achieved by employing either acetaldehyde diethyl acetal or paraldehyde in the presence of trifluoroacetic acid and pyridine or PPTS.…”

Section: Calanolide Synthetic Analogsmentioning

confidence: 99%

Coumarins as Inhibitors of HIV Reverse Transcriptase

Kostova

2006

CHR

148

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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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Total Synthesis of (±)-Calanolide A

Cited by 20 publications

References 13 publications

Recent progress in the development of coumarin derivatives as potent anti‐HIV agents

Recent progress in the development of coumarin derivatives as potent anti‐HIV agents

Structure‐Activity Relationships of Synthetic Coumarins as HIV‐1 Inhibitors

Coumarins as Inhibitors of HIV Reverse Transcriptase

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