Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers

Journal of Medicinal Chemistry

Volumn 39, Issue 6, 1996, Pages 1303-1313

  Flavin, Michael T ^a   Rizzo, John D ^a   Khilevich, Albert ^a   Kucherenko, Alla ^a   Sheinkman, Abram K ^a   Vilaychack, Vilayphone ^a   Lin, Lin ^a   Chen, Wei ^a   Greenwood, Eugenia Mata ^b   Pengsuparp, Thitima ^b   Pezzuto, John M ^b   Hughes, Stephen H ^c   Flavin, Thomas M ^a   Cibulski, Michael ^a   Boulanger, William A ^a   Shone, Robert L ^a   Xu, Ze Qi ^a  

^a MediChem Research Inc   (United States)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^c NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; CALANOLIDE A;

ANTIVIRAL ACTIVITY; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; REVIEW; STRUCTURE ACTIVITY RELATION;

ANTIVIRAL AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COUMARINS; DNA-DIRECTED DNA POLYMERASE; HIV; HIV-1 REVERSE TRANSCRIPTASE; PYRANOCOUMARINS; RNA-DIRECTED DNA POLYMERASE; STEREOISOMERISM;

EID: 13344277278     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950797i     Document Type: Review

References (78)

1. Gallo, R. C.; Montagnier, L. AIDS in 1988. Sci. Am. 1988, 259 (4), 41-48.
2. Larder, B. A.; Darby, G.; Richmann, D. D. HIV with Reduced Sensitivity to Zidovudine (AZT) Isolated during Prolonged Therapy. Science 1989, 243, 1731-1734.
3. Lambert, J. S.; Seidlin, M.; Reichman, R. C.; Plank, C. S.; Laverty, M.; Morse, G. D.; Knupp, C.; McLaren, C.; Pettinelli, C.; Valentine, F. T.; Dolin, R. 2′,3′-Dideoxyinosine (ddI) in Patients with the Acquired Immunodeficeincy Syndrome or AIDS Related Complex. A Phase I Trial. N. Engl. J. Med. 1990, 322, 1333-1340.
4. Cooley, T. P.; Kunches, L. M.; Saunders, C. A.; Ritter, J. K.; Perkins, C. J.; McLaren. C.; McCaffrey, R. P.; Liebman, H. A. Once-Daily Administration of 2′,3′-Dideoxymosine (ddI) in Patients with the Acquired Immunodeficiency Syndrome or AIDS Related Complex Results of a Phase I Trial. N. Engl. J. Med. 1990, 322, 1340-1345
5. Richman, D. D. HIV Drag Resistance. AIDS Res. Hum. Retroviruses 1992, 8, 1065-1071.
6. Larder, B. A. Interaction between Drug Resistance Mutations in Human Immunodeficiency Virus Type 1 Reverse Transcriptase. J. Gen. Virol. 1994, 75, 951-907.
7. Mayers, D. L.; Japour, A. J.; Arduino, J. M.; Hammer, S. M.; Reichman, R.; Wagner, K. F.; Chung, R.; Lane, J.; Crumpacker, C. S.; McLeod, G. X.; Beckett, L. A.; Roberts, C. R.; Weislow, D.; Burks, D. D.; The RV43 Study Group. Dideoxynucleoside Resistance Emerges with Prolonged Zidovudine Monotherapy. Antimicrob. Agents Chemother. 1994, 38, 307-314.
8. Erice, A.; Mayers, D. L.; Strike, D. G.; Sannerud, K. J.; McCutchan, F. E.; Henry, K.; Balfour, H. H., Jr. Brief Report: Primary Infection with Zidovudine-Resistant Human Immunodeficiency Virus Type 1. N. Engl. J. Med. 1993, 328, 1163-1165.
9. Paul, W. E. Reexamining AIDS Research Priorities. Science 1995, 267, 633-636.
10. Romero, D. L. Advances in the Development of HIV Reverse Transcriptase Inhibitors. In Annual Reports in Medicinal Chemistry, Bristol, J. A., Ed.; Academic Press, Inc.: New York, 1994; Vol. 29, pp 123-132.
11. Brookmeyer, R. Reconstruction and Future Trends of the AIDS Epidemic In the United States. Science 1991, 253, 37-42.
12. Brain, M. M.; Heyward, W. L.; Curran, J. W. The Global Epidemiology of HIV Infection and AIDS. Annu. Rev. Microbiol. 1990, 44, 555-577.
13. De Clereq, E. HIV-1-Specific RT Inihibitors: Highly Selective Inhibitors of Human Immunodeficiency Virus Type 1 that Are Specifically Targeted at the Viral Reverse Transcriptase. Med. Res. Rev. 1993, 13, 229-258.
14. Thaisrivongs, S. HIV Protease Inhibitors. In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed.; Academic Press, Inc.: New York, 1994; Vol. 29, pp 133-144.
15. Weislow, O. S.; Kiser, R.; Fine, D. L.; Bader, J.; Shoemaker, R. H.; Boyd, M. R. New Soluble-Formazan Assay for HIV-I Cytopathic Effects: Application to High-Flux Screening of Synthetic and Natural Products for AIDS-Antiviral Activity. J. Natl. Cancer Inst. 1989, 81, 577-586.
16. Mitsuya, H.; Yarchoan, R.; Broder, S. Molecular Targets for AIDS Therapy. Science 1990, 249, 1533-1544.
17. Arnold, E.; Arnold, G. F. Human Immunodeficiency Virus Structure: Implications for Antiviral Design. Adv. Virus Res. 1991, 39, 1-87.
18. Vaishnav, Y. N.; Wong-Staal, F. The Biochemistry of AIDS. Annu. Rev. Biochem. 1991, 60, 577-630.
19. Goff, S. P. Retroviral Reverse Transcriptase: Synthesis, Structure, and Function. J. AIDS 1990, 3, 817-831.
20. Jacobo-Molina, A.; Arnold, E. HIV Reverse Transcriptase Structure-Function Relationships. Biochemistry 1991, 30, 6351-6361.
21. De Clercq, E. HIV Inhibitors Targeted at the Reverse Transcriptase. AIDS. Res. Hum. Retroviruses 1992, 8, 119-134.
22. Kohlstaedt, L. A.; Wang, J.; Friedman, J. M.; Rice, P. A.; Steitz, T. A. Crystal Structure at 3.5 A Resolution of HIV-1 Reverse Transcriptase Complexed with an. Inhibitor. Science 1992, 256, 1783-1790.
23. Smerdon, S. J.; Jager, J.; Wang, J ; Kohlstaedt, L. A.; Chirino, A. J.; Friedman, J. M.; Rice, P. A.; Steitz, T. A. Structure of the Binding Site for Nonnucleoside Inhibitors of the Reverse Transcriptase of Human Immunodeficiency Virus Type 1. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3911-3915.
24. Ren, J.; Esnouf, R.; Garman, E.; Somers, D.; Ross, C.; Kirby, I.; Keeling, J.; Darby, G.; Jones, Y.; Stuart, D.; Stammers, D. High Resolution Structures of HIV-1 RT from Four RT-Inhibitor Complexes. Nature Struct. biol. 1995, 2, 293-302.
25. Ding, J.; Das, K.; Moereels, H.; Koymans, L.; Andries, K.; Janssen, P. A. J.; Hughes, S. H.; Arnold, E. Structure of HIV-1 RT/TIBO R 86183 Complex Reveals Similarity in the Binding of Diverse Nonnucleoside Inhibitors. Nature Struct. Biol. 1995, 2, 407-415.
26. Ren, J.; Esnouf, R.; Hopkins, A.; Ross, C.; Jones, Y.; Stammers, D.; Stuart, D. The Structure of HIV-1 Reverse Transcriptase Complexed with 9-Chloro-TIBO: Lessons for Inhibitor Design. Structure 1995, 3, 915-926.
27. Ding, J.; Das, K; Tantillo, C.; Zhang, W.; Clark, A. D., Jr.; Jessen, S.; Lu, X.; Hsiou, Y.; Jacobo-Molina, A.; Andries, K.; Pauwels, R.; Moereels, H.; Koymans, L.; Janssen, P. A. J.; Smith, R. H., Jr.; Kreoger Koepke, M.; Michejda, C. J.; Hughes, S. H.; Arnold, E. Structure of HIV-1 Reverse Transcriptase in a Complex with the Non-nucleoside Inhibitor α-APA R 95845 at 2.8Å Resolution. Structure 1995, 3, 365-379.
28. Spence, R. A.; Kati, W. M.; Anderson, K. S.; Johnson, K. A. Mechanism of Inhibition of HIV-1 Reverse Transcriptase by Nonnucleoside Inhibitors. Science 1995, 267, 988-993.
29. Esnouf, R.; Ren, J.; Ross, C.; Jones, Y.; Stammers, D.; Stuart, D. Mechanism of Inhibition of HIV-1 Reverse Transcriptase by Non-nucleoside Inhibitors. Nature Struct. Biol. 1995, 2, 303-308.
30. Rittinger, K.; Divita, G.; Goody, R. Human Immunodeficiency Virus Reverse Transcriptase Substrate-Induced Conformational Changes and the Mechanism of Inhibition by Nonnucleoside Inhibitors. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 8046-8049.
31. Mellors, J. W.; Larder, B. A.; Schinazi, R. F. Mutations in HIV-1 Reverse Transcription and Protease Associated with Drug Resistance, Int. Antiviral News 1995, 3, 8-13.
32. 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.
33. Patil, A. D.; Freyer, A. J.; Eggleston, D. S.; Haltiwanger, R. C.; Bean, M. F.; Taylor, P. B.; Caranfa, M. J.; Breen, A. L.; Bartus, H. R.; Johnson, R. K.; Hertzberg, R. P.; Westley, J. W. The Inophyllums, Novel Inhibitors of HTV-1 Reverse Transcriptase Isolated from the Malaysian Tree, Calophyllum inophyllum Linn. J. Med. Chem. 1993, 36, 4131-4138.
34. 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.
35. 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.
36. Taylor, P. B.; Culp, J. S.; Debouck, C.; Johnson, R. K.; Patil, A. D.; Woolf, D. J.; Brooks, I.; Hertzberg, R. P. Kinetic and Mutational Analysis of Human Immunodeficiency Virus Type 1 Reverse Transcriptase Inhibition by Inophyllums, a Novel Class of Non-nucleoside Inhibitors. J. Biol. Chem. 1994, 269, 6325-6331.
37. Buckheit, R. W., Jr.; Fliakas-Boltz, V.; Decker, W. D.; Roberson, J. L.; Stup, T. L.; Pyle, C. A.; White, E. L.; McMahon, J. B.; Currens, M. J.; Boyd, M. R.; Bader, J. P. Comparative Anti-HIV Evaluation of Diverse HTV-1-specific Reverse Transcriptase Inhibitor-resistant Virus Isolates Demonstrates the Existence of Distinct Phenotypic Subgroups. Antiviral Res. 1995, 26, 117-132.
38. De Clercq, E. How to Overcome Resistance of HIV-1-specific Reverse Transcriptase Inhibitors. AIDS 1994, 8, 1020-1021.
39. 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.
40. Chenera, B.; West, M. L.; Finkelstein, J. A.; Dreyer, G. B. Total Synthesis of (±)-Calanolide A, a Non-Nucleoside Inhibitor of HIV-1 Reverse Transcriptase. J. Org. Chem. 1993, 58, 5605-5606 and the supplementary material provided.
41. Palmer, C. J.; Josephs, J. L. Synthesis of the Calophyllum Coumarins. Tetrahedron Lett. 1994, 35, 5363-5366.
42. Rama Rao, A. V.; Gaitonde, A. S.; Prakash, K. R. C.; Prahlada Rao, S. A Concise Synthesis of Chiral 2-Methyl Chroman-4-ones: Stereoselective Build-up of the Chromanol Moiety of Anti-HIV Agent, Calanolide A. Tetrahedron Lett. 1994, 35, 6347-6350.
43. Deshpande, P. P.; Tagliaferri, F.; Victory, S. P.; Yan, S.; Baker, D. C. Synthesis of Optically Active Calanolides A and B. J. Org. Chem. 1995, 58, 2964-2965.
44. Sethna, S.; Phadke, R. The Pechmann Reaction. Org. React. 1953, 7, 1-58.
45. Crombie, L.; Jones, R. C. F.; Palmer, C. J. Synthesis of the Mammea Coumarins. Part 1. The Coumarins of the Mammea A. B, and C Series. J. Chem. Soc., Perkin Trans, 1 1987, 317-331 and references cited therein.
46. Josephy, P. D.; Damme, A. V. Reaction of Gibbs Reagent with Para-Substituted Phenols. Anal. Chem. 1984, 56, 813-814.
47. Friedel Crafts and Related Reactions; Olah, G. A., Ed.; Wiley: New York, 1963; Vol. 3.
48. Ahluwalia, V. K.; Kumar, D.; Sunita, D. Studies in 4-Phenyl-coumarins: Some Unusual Observations. Indian J. Chem. 1975, 13, 546-548.
49. Barton, D. H. B.; Donnelly, D. M. X.; Finet, J. P.; Guiry, P. J. Total Synthesis of Isorobustin. Tetrahedron Lett. 1990, 31, 7449-7452.
50. Szell. T. Synthesis of 2,3-Disubstituted Chromones: Cyclisation of the Enol-ester of o-Acyloxyphenyl Ketones. J. Chem. Soc. C 1967, 2041-2044.
51. Szell, T.; Kovacs, K.; Zarandy, M. S.; Erdohelyi, A. Cyclisation of the Enol Esters of o-Acyloxyphenyl Ketones, IV. A Kinetic Study of the Steps of the Kostanecki-Robinson Reaction. Helv. Chim. Acta 1969, 52, 2636-2641.
52. Gemal, A. L.; Luche, J.-L. Lanthanoids in Organic Synthesis. 6. The Reduction of α-Enones by Sodium Borohydride in the Presence of Lanthanoid Chlorides: Synthetic and Mechanistic Aspects. J. Am Chem. Soc. 1981, 103, 5454-5459.
53. Narisada, M.; Horibe, I.; Watanabe, F.; Takeda, K. Selective Reduction of Aryl Halides and α,β-Unsaturated Esters with Sodium Borohydride-Cuprous Chloride in Methanol and Its Application to Deuterium Labeling. J. Org. Chem. 1989, 54, 5308-5313.
54. Fung, N. Y. M.; de Mayo, P.; Schauble, J. H.; Weedon, A. C. Reduction by Tributyltin Hydride of Carbonyl Compounds Adsorbed on Silica Gel: Selective Reduction of Aldehydes. J. Org. Chem. 1978, 43, 3977-3979.
55. Cabrera, A.; Alper, H. Samarium(II) Iodide-HMPA: A Very Efficient System for the Selective Reduction of α,β-Unsaturated Carbonyl Compounds. Tetrahedron Lett. 1992, 33, 5007-5008.
56. 6. Compatibility with Halogen, Sulfonate, and γ-Oxygen and Sulfur Substituents. Tetrahedron Lett, 1990, 31, 3237-3240.
57. Tilak, B. D.; Muljiani, Z. Synthesis of Chromans and Benzopyrylium Salts Involving Hydride Transfer. Tetrahedron 1968, 24, 949-957.
58. Yamada, K. Reduction of Pyrones with Complex Metal Hydrides. Bull. Chem. Soc. Jpn. 1962, 35, 1329-1334 and references cited therein.
59. 2-Prompted Electron Transfer Process. Chem. Lett. 1991, 2117-2118.
60. Freeman, J. P.; Hawthorne, M. F. The Action of Lithium Aluminum Hydride and Organometallic Reagents on 4-Hydroxycoumarin. J. Am. Chem. Soc. 1956, 78, 3366-3369.
61. Aldol products were observed in the LDA reaction. These results will be published separately.
62. Naemura, K.; Fukuda, R.; Konishi, M.; Hirose, K.; Tobe, Y. LipaseYS-catalysed Acylation of Alcohols: a Predictive Active Site Model for Lipase YS to Identify which Enantiomer of a Primary or a Secondary Alcohol Reacts Faster in this Acylation. J. Chem. Soc., Perhin Trans. 1 1994, 1203-1256.
63. Parida, S.; Dordick, J. S. Tailoring Lipase Specificity by Solvent and Substrate Chemistries. J. Org. Chem, 1993, 58, 3238-3244.
64. After this work was completed, we became aware of similar work published in the literature; see: Cardellina, J. H., II; Bokesch, H. R.; McKee, T. C.; Boyd, M. R. Resolution and Comparative Anti-HIV Evaluation of the Enantiomers of Calanolides A and B. Bioorg. Med. Chem. Lett. 1995, 5, 1011-1014.
65. Pengsuparp, T.; Cai, L.; Constant, H.; Fong, H. S. S.; Lin, L.-Z.; Kinghorn, A. D.; Pezzuto, J. M.; Cordell, G. A.: Ingolfsdottir, K.; Wagner, H.; Hughes, S. H. Mechanistic Evaluation of New Plant-Derived Compounds That Inhibit HIV-1 Reverse Transcriptase. J. Nat. Prod. 1995, 58, 1024-1031.
66. White, E. L.; Parker, W. B.; Macy, L. J.; Shaddix, S. C.; McCaleb, G.; Secrist, J. A., III; Vince, R.; Shannon, W. M. Comparison of the Effect of Carbovir, AZT, and Dideoxynucleoside Triphosphates on the Activity of Human Immunodeficiency Virus Reverse Transcriptase and Selected Human Polymerases. Biochem. Biophys. Res. Commun. 1989, 161, 393-398.
67. Parker, W. B.; White, E. L.; Shaddix, S. C.; Ross, L. J.; Buckheit, R. W., Jr.; Germany, J. M.; Secrist. J. A., III; Vince, R.; Shannon, W. M. Mechanism of Inhibition of Human Immunodeficiency Virus Type 1 Reverse Transcriptase and Human DNA Polymerases α, β, and γ by the 5′-Triphosphates of Carbovir, 3′-Azido-3′-deoxythymidine, 2′,3′-Dideoxyguanosine, and 3′-Deoxythymidine. J. Biol. Chem. 1991, 266, 1754-1762.
68. Pengsuparp, T.; Pezzuto, J. M. Unpublished observations.
69. 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. Bioorg. Med. Chem. Lett. 1994, 4, 1961-1964.
70. For the convenience of comparison and discussion, we suggest referring to soulattrolide as (-)-inophyllum P (4) from now on and referring to costatolide as (-)-calanolide B (3) as suggested in ref 64.
71. McKee, T. C.; Cardellina, J. H., II; Dreyer, G. B.; Boyd, M. R. The Pseudocalanolides: Structure Revision of Calanolides C and D. J. Nat. Prod. 1995, 58, 916-920.
72. Gustafson, K. R.; Bokesch, H. R.; Fuller, R. W.; Cardellina, J. H., II; Kadushin, M. R.; Soejarto, D. D.; Boyd, M. R. Calanone, a Novel Coumarin from Calophyllum teysmannii. Tetrahedron Lett. 1994, 35, 5821-5824.
73. Gunasekera, S. P.; Jayatilake, G. S.; Selliah, S. S., Sultanbawa, M. U. S. Chemical Investigation of Ceylonese Plants. Part 27. Extractives of Calophyllum cuneifolium Thw. and Calophyllum soulattri Burm. f. (Guttiferae). J. Chem. Soc., Perkin Trans, 1 1977, 1505-1511.
74. Gulakowski, R. J.; McMahon, J. B.; Staley, P. G.; Moran, R. A.; Boyd, M. R. A Semiautomated Multiparameter Approach for Anti-HIV Drug Screening. J. Virol. Methods 1991, 33, 87-100.
75. Clark, P. K.; Ferris, A. L.; Miller, D. A.; Hizi, A.; Kim, K-W.; Deringer-Boyer, S. M.; Mellini, M. L.; Clark, A. D., Jr.; Arnold, G. F.; Lebherg, W. B., III; Arnold. E.; Muschik, G. M.; Hughes, S. H. HIV-1 Reverse Transcriptase Purified from a Recombinant Strain of Escherichla coli. AIDS Res. Hum. Retroviruses 1990, 6, 753-764.
76. Hizi, A.; Tal, R.; Hughes, S. H. Mutational Analysis of the DNA Polymerase and Ribonuclease H Activities of Human Immunodeficiency Virus Type 2 Reverse Transcriptase Expressed in Escherichia coli. Virology 1991, 180, 339-346.
77. Tan, G. T.; Pezzuto, J. M.; Kinghorn, A. D. Evaluation of Natural Products as Inhibitors of Hum an Immunodeficiency Virus Type 1 (HIV-1) Reverse Transcriptase. J. Nat. Prod. 1991, 54, 143-154.
78. Tan, G. T.; Kinghorn, A. D.; Hughes, S. H.; Pezzuto, J. M. Psychotrine and Its O-Methyl Ether are Selective Inhibitors of Human Immunodeficiency Virus-1 Reverse Transcriptase. J. Biol. Chem. 1991, 266, 23529-23536.