In vitro platelet-activating factor receptor binding inhibitory activity of pinusolide derivatives: A structure-activity study

Journal of Medicinal Chemistry

Volumn 41, Issue 14, 1998, Pages 2626-2630

  Han, Byung Hoon ^a   Yang, Hyun Ok ^a   Kang, Young Hwa ^a   Suh, Dae Yeon ^a   Go, Hyun Jung ^a   Song, Wan Jin ^a   Kim, Yong Chul ^a   Park, Man Ki ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; PINUSOLIDE; THROMBOCYTE ACTIVATING FACTOR; THROMBOCYTE ACTIVATING FACTOR ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG SOLUBILITY; MEDICINAL PLANT; RECEPTOR BINDING; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BLOOD PLATELETS; DITERPENES; PLATELET ACTIVATING FACTOR; PLATELET AGGREGATION INHIBITORS; PLATELET MEMBRANE GLYCOPROTEINS; RABBITS; RECEPTORS, CELL SURFACE; RECEPTORS, G-PROTEIN-COUPLED; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0003027380     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970569j     Document Type: Article

References (30)

1. (a) Benveniste, J.; Henson, P. M.; Cochrane, C. G. Leucocyte dependent histamine release from rabbit platelets: The role of IgE, basophils and a platelet activating factor. J. Exp. Med. 1972, 136, 1356-1377.
2. (b) Braquet, P.; Tougui, L.; Shen, T. Y.; Vargaftig, B. B. Perspectives in platelet-activating factor research. Pharmacol. Rev. 1987, 39, 97-145.
3. (a) Hanahan, D. J. Platelet activating factor: A biologically active phosphoglyceride. Annu. Rev. Biochem. 1987, 55, 483-509.
4. (b) Prescott, S. M.; Zimmerman, G. A.; McIntyre, T. M. Platelet-activating factor. J. Biol. Chem. 1991, 265, 17381-17384.
5. (c) Koltai, M.; Hosford, D.; Braquet, P. G. Platelet-activating factor and its antagonists in allergic and inflammatory disorders. Clin. Allergy Immunol. 1996, 8, 463-489.
6. (d) Yin, M.; Buurman, W. A.; Daemen, J.-W. H. C.; Kootstra, G. The PAF antagonist TCV-309 reduces graft PMN infiltration and enhances early function of 24-hour-preserved rat kidneys with long warm ischemia. Transplantation 1996, 61, 1443-1446.
7. (a) Honda, Z.; Nakamura, M.; Miki, I.; Minami, M.; Watanabe, T.; Seyama, Y.; Okado, H.; Toh, H.; Ito, K.; Miyamoto, T.; Shimizu, T. Cloning by functional expression of platelet-activating factor receptor from guinea-pig lung. Nature 1991, 349, 342-346.
8. (b) Nakamura, M.; Honda, Z.; Izumi, T.; Sakanaka, C.; Mutoh, H.; Minami, M.; Bito, H.; Seyama, Y.; Matsumoto, T.; Noma, M.; Shimizu, T. Molecular cloning and expression of platelet-activating factor receptor from human leukocytes. J. Biol. Chem. 1991, 266, 20400-20405.
9. (a) Kawakami, Y.; Kitani, H.; Yuasa, S.; Abe, M.; Moriwaki, M.; Kagoshima, M.; Terasawa, M.; Tahara, T. Structural optimization of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4] diazepines as antagonists for platelet activating factor: pharmacological contribution of substituents at the 2-and 6-positions of a condensed ring system. Eur. J. Med. Chem. 1996, 31, 683-692.
10. (b) Sugano, M.; Sato, A.; Saito, K.; Takaishi, S.; Matsushita, Y.; Iijima, Y. Structure-activity relationships of phomactin derivatives as platelet activating factor antagonists. J. Med. Chem. 1996, 39, 5281-5284.
11. (c) Chung, S. K.; Ban, S. H.; Kim, S. H.; Kim, B. E.; Woo, S. H. Synthesis and bioactivities of heterocyclic lipids as PAF antagonists. 2. Bioorg. Med. Chem. Lett. 1995, 5, 1097-1102.
12. (a) Batt, J. P.; Lamouri, A.; Tavet, F.; Heymans, F.; Dive, G.; Godfroid, J.-J. New hypothesis of the conformation of the PAF-receptor from studies on the geometry of selected platelet-activating factor-antagonists. J. Lipid Mediators 1991, 4, 343-346.
13. (b) Godfroid, J.-J.; Dive, G.; Lamotte-Brasseur, J.; Batt, J. P.; Heymans, F. PAF receptor structure: A hypothesis. Lipids 1991, 26, 1162-1166.
14. (a) Yang, H. O.; Suh, D.-Y.; Han, B. H. Isolation and characterization of platelet-activating factor receptor binding antagonists from Biota orientalis. Planta Med. 1995, 61, 37-40.
15. (b) Yang, H. O.; Kang, Y. H.; Suh, D.-Y.; Han, B. H. Biological and pharmacological effects of pinusolide, a novel platelet activating factor antagonist. Planta Med. 1995, 61, 519-522.
16. Yang, H. O.; Han, B. H. Pinusolidic acid: A platelet-activating factor inhibitor from Biota orientalis. Planta Med. 1998, 64, 73-74.
17. McMurry, J. E.; Donovan, S. F. A method for the synthesis of β-alkylidenebutyrolactones, 3-substituted butenolides, and 3-substituted furans. Tetrahedron Lett. 1977, 33, 2869-2872.
18. (a) Kakis, F. J.; Fetizon, M.; Douchkine, N.; Golfier, M.; Mourgues, P.; Prange, T. Mechanistic studies regarding the oxidation of alcohols by silver carbonate on Celite. J. Org. Chem. 1974, 39, 523-533.
19. (b) Chakraborty, T. K.; Chandrasekaran, S. Efficient transformation of (Z)-2-butene-1,4-diols to α,β-butenolides: a simple synthesis of (±)-eldanolide. Tetrahedron Lett. 1984, 25, 2891-2894.
20. (a) Bergbreiter, D. E.; Rainville, D. P. Stereochemistry of hydroboration-oxidation of terminal alkenes. J. Org. Chem. 1978, 41, 3031-3033.
21. (b) Kabalka, G. W.; Newton, R. J., Jr.; Jacobus, J. Stereochemistry of the hydroboration of alkenes. J. Org. Chem. 1978, 43, 1567-1569.
22. Mukherjee, D.; Wu, Y.-D.; Fronczek, F. R.; Houk, K. N. Experimental tests of models to predict nucleophilic addition stereochemistries. J. Am. Chem. Soc. 1988, 110, 3328-3330.
23. Hassall, C. H. The Baeyer-Villiger oxidation of aldehydes and ketones. Org. React. (N. Y.) 1957, 9, 73-106.
24. Song, W.-J.; Suh, D.-Y.; Rang, Y.-H.; No, K.; Han, B. H. Oxidation of pinusolide, via an iodohydrin intermediate, to 17-hydroxy-8,13-labdadien-6,15-olid-9-oic acid methyl ester by treatment with iodic acid or periodic acid in aqueous acetone. Bull. Kor. Chem. Soc. 1998, 19.
25. Corey, E. J.; Schmidt, G. Useful procedures for the oxidation of alcohols involving pyridinium dichromate in aprotic media. Tetrahedron Lett. 1979, 5, 399-402.
26. (a) Chung, S.-K. Selective reduction of mono- and disubstituted olefins by sodium borohydride and cobalt(II). J. Org. Chem. 1979, 44, 1014-1016.
27. 4. Tetrahedron Lett. 1984, 25, 2501-2504.
28. (a) Valone, F. H.; Coles, E.; Reinhold, V. R.; Goetzl, E. J. Specific binding of phospholipid platelet activating factor by human platelets. J. Immunol. 1982, 129, 1637-1641.
29. (b) Kloprogge, E.; Akkerman, N. Binding kinetics of PAF-acether (1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine) to intact human platelets. Biochem. J. 1984, 223, 901-909.
30. Terashita, Z.; Tsushima, S.; Yoshioka, Y.; Nomura, H.; Inada, Y.; Nishikawa, K. CV 3988-a specific antagonist of platelet activating factor (PAF). Life Sci. 1983, 32, 1975-1982.