Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B

Journal of Medicinal Chemistry

Volumn 39, Issue 22, 1996, Pages 4507-4510

  Galinis, Deborah L ^a,b   Fuller, Richard W ^a   McKee, Tawnya C ^a   Cardellina II, John H ^a   Gulakowski, Robert J ^a   McMahon, James B ^a   Boyd, Michael R ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; CALANOLIDE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; STRUCTURE ACTIVITY RELATION; VIRUS INHIBITION;

ANTI-HIV AGENTS; ANTIVIRAL AGENTS; COUMARINS; CYTOPATHOGENIC EFFECT, VIRAL; HUMANS; PYRANOCOUMARINS; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0029956809     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9602827     Document Type: Article

References (17)

1. Part 30 in the series HIV-Inhibitory Natural Products. For part 29, see: McKee, T. C.; Fuller, R. W.; Covington, C. D.; Cardellina, J. H., II; Gulakowski, R. J.; Krepps, B. L.; McMahon, J. B.; Boyd, M. R. New pyranocoumarins isolated from Calophyllum lanigerum and Calophyllum teysmannii. J. Nat. Prod. 1996, 59, 754-758.
2. Kashman, Y.; Gustafson, K. R.; Fuller, R. W.; Cardellina, J. H., II; McMahon, J. B.; Currens, M. J.; Buckheit, R. W., Jr.; Hughes, S. H.; Cragg, G. M.; Boyd, M. R. The calanolides, a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum. J. Med. Chem. 1992, 35, 2735-2743.
3. (a) Hizi, A.; Tal, R.; Shaharabany, M.; Currens, M. J.; Boyd, M. R.; Hughes, S. H.; McMahon, J. B. Specific inhibition of the reverse transcriptase of human immunodeficiency virus type 1 and the chimeric enzymes of human immunodeficiency virus type 1 and type 2 by nonnucleoside inhibitors. Antimicrob. Agents Chemother. 1993, 37, 1037-1042.
4. (b) Boyer, P. L.; Currens, M. J.; McMahon, J. B.; Boyd, M. R.; Hughes, S. H. Analysis of nonnucleoside drug-resistant variants of human immunodeficiency virus type 1 reverse transcriptase. J. Virol. 1993, 67, 2412-2420.
5. (c) Buckheit, R. W., Jr.; Fliakas-Boltz, V.; Decker, W. D.; Roberson, J. L.; Pyle, C. A.; White, E. L.; Bowden, B. J.; McMahon, J. B.; Boyd, M. R.; Bader, J. P.; Nickell, D. G.; Barth, H.; Antonucci, T. K. Biological and biochemical anti-HIV activity of the benzothiadiazine class of nonnucleoside reverse transcriptase inhibitors. Antiviral Res. 1994, 25, 43-56.
6. (d) Currens, M. J.; Gulakowski, R. J.; Mariner, J. M.; Moran, R. A.; Buckheit, R. W., Jr.; Gustafson, K. R.; McMahon, J. B.; Boyd, M. R. Antiviral activity and mechanism of action of calanolide A against the human immunodeficiency virus. J. Pharmacol. Exp. Ther., in press.
7. (e) Currens, M. J.; Mariner, J. M.; McMahon, J. B.; Boyd, M. R. Kinetic analysis of inhibition of HIV-1 reverse transcriptase by calanolide A. J. Pharmacol. Exp. Ther., in press.
8. Fuller, R. W.; Bokesch, H. R.; Gustafson, K. R.; McKee, T. C.; Cardellina, J. H., II; McMahon, J. B.; Cragg, G. M.; Soejarto, D. D.; Boyd, M. R. HIV-Inhibitory coumarins from latex of the tropical rainforest tree Calophyllum teysmannii var. inophylloide. BioMed. Chem. Lett. 1994, 4, 1961-2964.
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13. (a) Kucherenko, A.; Flavin, M. T.; Boulanger, W. A.; Khilevich, A.; Shone, R. L.; Rizzo, J. D.; Sheinkman, A. K.; Xu, Z-Q. Novel approach for synthesis of (±)-calanolide A and its anti-HIV activity. Tetrahedron Lett. 1995, 36, 5475-5478.
14. (b) Palmer, C. J.; Josephs, J. L. Synthesis of Calophyllum coumarins. Tetrahedron Lett. 1994, 35, 5363-5366.
15. Since the completion of this work, several approaches to chiral syntheses of the calanolides have been published: (a) Rama Rao, A. V.; Gaitonde, A. S.; Prakash, K. R. C.; Prahlada Rao, S. A concise synthesis of chiral 2-methyl chroman-4-ones: stereo-selective build-up of the chromanol moiety of anti-HIV agent, calanolide A. Tetrahedron Lett. 1994, 35, 6347-6450. (b) Deshpande, P. P.; Baker, D. C. A simple approach to the synthesis of the chiral substituted chroman ring of Calophyllum coumarins. Synthesis 1995, 630-632. (c) Deshpande, P. P.; Tagliaferri, F.; Victory, S. F.; Yan, S.; Baker, D. C. Synthesis of optically active calanolide A and B. J. Org. Chem. 1995, 60, 2964-2965.
16. Since the completion of this work, several approaches to chiral syntheses of the calanolides have been published: (a) Rama Rao, A. V.; Gaitonde, A. S.; Prakash, K. R. C.; Prahlada Rao, S. A concise synthesis of chiral 2-methyl chroman-4-ones: stereo-selective build-up of the chromanol moiety of anti-HIV agent, calanolide A. Tetrahedron Lett. 1994, 35, 6347-6450. (b) Deshpande, P. P.; Baker, D. C. A simple approach to the synthesis of the chiral substituted chroman ring of Calophyllum coumarins. Synthesis 1995, 630-632. (c) Deshpande, P. P.; Tagliaferri, F.; Victory, S. F.; Yan, S.; Baker, D. C. Synthesis of optically active calanolide A and B. J. Org. Chem. 1995, 60, 2964-2965.
17. Since the completion of this work, several approaches to chiral syntheses of the calanolides have been published: (a) Rama Rao, A. V.; Gaitonde, A. S.; Prakash, K. R. C.; Prahlada Rao, S. A concise synthesis of chiral 2-methyl chroman-4-ones: stereo-selective build-up of the chromanol moiety of anti-HIV agent, calanolide A. Tetrahedron Lett. 1994, 35, 6347-6450. (b) Deshpande, P. P.; Baker, D. C. A simple approach to the synthesis of the chiral substituted chroman ring of Calophyllum coumarins. Synthesis 1995, 630-632. (c) Deshpande, P. P.; Tagliaferri, F.; Victory, S. F.; Yan, S.; Baker, D. C. Synthesis of optically active calanolide A and B. J. Org. Chem. 1995, 60, 2964-2965.