Synthesis and immunosuppressive activity of 2-substituted 2- aminopropane-1,3-diols and 2-aminoethanols

Journal of Medicinal Chemistry

Volumn 43, Issue 15, 2000, Pages 2946-2961

  Kiuchi, Masatoshi ^a   Adachi, Kunitomo ^a   Kohara, Toshiyuki ^a   Minoguchi, Masanori ^a   Hanano, Tokushi ^a   Aoki, Yoshiyuki ^a   Mishina, Tadashi ^a   Arita, Masafumi ^a   Nakao, Noriyoshi ^a   Ohtsuki, Makio ^a   Hoshino, Yukio ^a   Teshima, Koji ^a   Chiba, Kenji ^a   Sasaki, Shigeo ^b   Fujita, Tetsuro ^c,d  

^a Welfide Corporation   (Japan)

^b Taito Company Research Laboratory   (Japan)

^c KYOTO UNIVERSITY   (Japan)

^d SETSUNAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FINGOLIMOD; IMMUNOSUPPRESSIVE AGENT;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG CONFORMATION; DRUG EFFECT; DRUG POTENCY; DRUG SYNTHESIS; IMMUNOREACTIVITY; IMMUNOSUPPRESSIVE TREATMENT; LYMPHOCYTE DEPLETION; NONHUMAN; ORGAN TRANSPLANTATION; RAT; SKIN ALLOGRAFT; STRUCTURE ACTIVITY RELATION;

ANIMALS; DRUG EVALUATION, PRECLINICAL; GRAFT REJECTION; IMMUNOSUPPRESSIVE AGENTS; INHIBITORY CONCENTRATION 50; LYMPH NODES; ORGAN SIZE; PROPYLENE GLYCOLS; RATS; RATS, INBRED F344; RATS, INBRED LEW; SKIN TRANSPLANTATION; SPHINGOSINE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; T-LYMPHOCYTES;

EID: 17144435270     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000173z     Document Type: Article

References (41)

1. Part of this study was reported in our preliminary communications: Adachi, K.; Kohara, T.; Nakao, N.; Arita, M.; Chiba, K.; Mishina, T.; Sasaki, S.; Fujita, T. Design, Synthesis, and Structure - Activity Relationships of 2-Substituted-2-amino-1,3-propanediols: Discovery of a Novel Immunosuppressant, FTY720. Bioorg. Med. Chem. Lett. 1995, 5, 853-856.
2. Kiuchi, M.; Adachi, K.; Kohara, T.; Teshima, K.; Masubuchi, Y.; Mishina, T.; Fujita, T. Synthesis and Biological Evaluation of 2,2-Disubstituted 2-Aminoethanols: Analogues of FTY720. Bioorg. Med. Chem. Lett. 1998, 8, 101-106.
3. Borel, J. F. Pharmacology of Cyclosporine (Sandimmune) IV. Pharmacological Properties in vivo. Pharmacol. Rev. 1990, 41, 259-371.
4. Peters, D. H.; Fitton, A.; Plosker, G. L.; Faulds, D. Tacrolimus: A Review of its Pharmacology, and Therapeutic Potential in Hepatic and Renal Transplantation. Drugs 1993, 46, 746-794.
5. Schreiber, S. L. Chemistry and Biology of the Immunophilins and Their Immunosuppressive Ligands. Science 1991, 251, 283-287.
6. Liu, J.; Farmer, J. D., Jr.; Lane, W. S.; Friedman, J.; Weissman, I.; Schreiber, S. L. Calcineurin is a Common Target of Cyclophilin-Cyclosporin A and FKBP-FK506 Complexes. Cell 1991, 66, 807-815.
7. Schreiber, S. L. Immunophilin-Sensitive Protein Phosphatase Action in Cell Signaling Pathways. Cell 1992, 70, 365-368.
8. European FK506 Multicentre Liver Study Group. Randomised Trial Comparing Tacrolimus (FK506) and Cyclosporin in Prevention of Liver Allograft Rejection. Lancet 1994, 344, 423-428.
9. Slapak, M.; Geoghagen, T.; Digard, N.; Ahmed, K.; Sharman, V. L.; Crockett, R. The Use of Ciclosporine in Combination with Azathioprine and Steroids in Renal Transplantation. Transplant. Proc. 1985, 17, 1222-1226.
10. Kokado, Y.; Ishibashi, M.; Jiang, H.; Takahara, S.; Sonoda, T. Low-Dose Ciclosporin, Mizoribine, and Prednisolone in Renal Transplantation: A New Triple-Drug Therapy. Clin. Transplant. 1990, 4, 191-197.
11. Fujita, T.; Inoue, K.; Yamamoto, S.; Ikumoto, T.; Sasaki, S.; Toyama, R.; Chiba, K.; Hoshino, Y.; Okumoto, T. Fungal Metabolites. Part 11. A Potent Immunosuppressive Activity Found in Isaria sinclairii Metabolite. J. Antibiot. 1994, 47, 208-215.
12. Kluepfel, D.; Bagli, J.; Baker, H.; Charest, M.-P.; Kudelski, A.; Sehgal, S. N.; Vezina, C. Myriocin, a New Antifungal Antibiotic from Myriococcum albomyces. J. Antibiot. 1972, 25, 109-115.
13. Bagli, J. F.; Kluepfel, D.; St-Jacques, M. Elucidation of Structure and Stereochemistry of Myriocin. A Novel Antifungal Antibiotic. J. Org. Chem. 1973, 38, 1253-1260.
14. Craveri, R.; Manachini, P. L.; Aragozzini, F. Thermozymocidin New Antifungal Antibiotic From a Thermophilic Eumycete. Experientia 1972, 28, 867-868.
15. Aragozzini, F.; Manachini, P. L.; Craveri, R.; Rindone, B.; Scolastico, C. Isolation and Structure Determination of a New Antifungal α-Hydroxymethyl-α-Amino Acid. Tetrahedron 1972, 28, 5493-5498.
16. Miyake, Y.; Kozutsumi, Y.; Nakamura, S.; Fujita, T.; Kawasaki, T. Serine Palmitoyltransferase is the Primary Target of a Sphingosine-like Immunosuppressant, ISP-I/Myriocin. Biochem. Biophys. Res. Commun. 1995, 211, 396-403.
17. Chen, J. K.; Lane, W. S.; Schreiber, S. L. The Identification of Myriocin-Binding Proteins. Chem. Biol. 1999, 6, 221-235.
18. VanMiddlesworth, F., Dufresne, C.; Wincott, F. E.; Mosley, R. T.; Wilson, K. E. Determination of the Relative and Absolute Stereochemistry of Sphingofungins A, B, C, and D. Tetrahedron Lett. 1992, 33, 297-300.
19. VanMiddlesworth, F.; Giacobbe, R. A.; Lopez, M.; Garrity, G.; Bland, J. A.; Bartizal, K.; Fromtling, R. A.; Polishook, J.; Zweerink, M.; Edison, A. M.; Rozdilsky, W.; Wilson, K. E.; Monaghan, R. L. Sphingofungins A, B, C, and D.; A New Family of Antifungal Agents. I. Fermentation, Isolation, and Biological Activity. J. Antibiot. 1992, 45, 861-867.
20. Horn, W. S.; Smith, J. L.; Bills, G. F.; Raghoobar, S. L.; Helms, G. L.; Kurtz, M. B.; Marrinan, J. A.; Frommer, B. R.; Thornton, R. A.; Mandala, S. M. Sphingofungins E and F: Novel Serinepalmitoyl Transferase Inhibitors from Paecilomyces variotii. J. Antibiot. 1992, 45, 1692-1696.
21. Zweerink, M. M.; Edison, A. M.; Wells, G. B.; Pinto, W.; Lester, R. L. Characterization of a Novel, Potent, and Specific Inhibitor of Serine Palmitoyltransferase. J. Biol. Chem. 1992, 267, 25032-25038.
22. Sasaki, S.; Hashimoto, R.; Kiuchi, M.; Inoue, K.; Ikumoto, T.; Hirose, R.; Chiba, K.; Hoshino, Y.; Okumoto, T.; Fujita, T. Fungal Metabolites. Part 14. Novel Potent Immunosuppressants, Mycestericins, Produced by Mycelia sterilia. J. Antibiot. 1994, 47, 420-433.
23. Fujita, T.; Hamamichi, N.; Matsuzaki, T.; Kitao, Y.; Kiuchi, M.; Node, M.; Hirose, R. Determination of the Absolute Configurations and Total Synthesis of New Immunosuppressants, Mycestericins E and G. Tetrahedron Lett. 1995, 36, 8599-8602.
24. Fujita, T.; Hamamichi, N.; Kiuchi, M.; Matsuzaki, T.; Kitao, Y.; Inoue, K.; Hirose, R.; Yoneta, M.; Sasaki, S.; Chiba, K. Determination of Absolute Configuration and Biological Activity of New Immunosuppressants, Mycestericins D, E, F and G. J. Antibiot. 1996, 49, 846-853.
25. Fujita, T.; Inoue, K.; Yamamoto, S.; Ikumoto, T.; Sasaki, S.; Toyama, R.; Yoneta, M.; Chiba, K.; Hoshino, Y.; Okumoto, T. Fungal Metabolites. Part 12. Potent Immunosuppressant, 14-Deoxomyriocin, (2S,3R,4A)-(E)-2-Amino-3,4-dihydroxy-2-hydroxymethyleicos-6-enoic acid and Structure - Activity Relationships of Myriocin Derivatives. J. Antibiot. 1994, 47, 216-224.
26. Fujita, T.; Yoneta, M.; Hirose, R.; Sasaki, S.; Inoue, K.; Kiuchi, M.; Hirase, S.; Adachi, K.; Arita, M.; Chiba, K. Simple Compounds, 2-Alkyl-2-amino-1,3-propanediols Have Potent Immunosuppressive Activity. Bioorg. Med. Chem. Lett. 1995, 5, 847-852.
27. Fujita, T.; Hirose, R.; Yoneta, M.; Sasaki, S.; Inoue, K.; Kiuchi, M.; Hirase, S.; Chiba, K.; Sakamoto, H.; Arita, M. Potent Immunosuppressants, 2-Alkyl-2-aminopropane-1,3-diols. J. Med. Chem. 1996, 39, 4451-4459.
28. Moore, G. J. Designing Peptide Mimetics. TiPS 1994, 15, 124-129.
29. Kornblum, N.; Ungnade, H. E. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, pp 724-727.
30. Kornblum, N.; Ungnade, H. E. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, pp 724-727.
31. Miyakoshi, T.; Du, Y.; Kumanotani, J. Synthesis of 3- and 4-(ω-Phenylalkyl)catechols, the Sap Exuded from a Burmese Lac Tree, Melanorrhoea Usitate. Bull. Chem. Soc. Jpn. 1991, 64, 1054-1056.
32. Ogura, K.; Ito, Y.; Tsuchihashi, G. A New Synthesis of Arylacetic Esters Starting from Aromatic Aldehyde by the Use of Methyl (Methylthio)methyl Sulfoxide. Bull. Chem. Soc. Jpn. 1979, 52, 2013-2022.
33. Young, R. N.; Gauthier, J. Y.; Coombs, W. The Methyl Group as a Protecting Group for Arylthiols: A Mild and Efficient Method for the Conversion of Methyl Aryl Sulfides to Arylthiols. Tetrahedron Lett. 1984, 25, 1753-1756.
34. Fujita, T.; Hirose, R.; Hamamichi, N.; Kitao, Y.; Sasaki, S.; Yoneta, M.; Chiba, K. 2-Substituted 2-Aminoethanol: Minimum Essential Structure for Immunosuppressive Activity of ISP-I (Myriocin). Bioorg. Med. Chem. Lett. 1995, 5, 1857-1860.
35. Plaut, H.; Ritter, J. J. A New Reaction of Nitriles. VI. Unsaturated Amides. J. Am. Chem. Soc. 1951, 73, 4076-4077.
36. Krimen, L. I.; Cota, D. J. The Ritter Reaction. Org. React. 1969, 17, 213-325.
37. Yanagawa, Y.; Masubuchi, Y.; Chiba, K. FTY720, A Novel Immunosuppressant, Induces Sequestration of Circulating Mature Lymphocytes by Acceleration of Lymphocyte Homing in Rats, III. Increase in Frequency of CD62L-Positive T cells in Peyer's Patches by FTY720-Induced Lymphocyte Homing. Immunology 1998, 95, 591-594.
38. Chiba, K.; Yanagawa, Y.; Masubuchi, Y.; Kataoka, H.; Kawaguchi, T.; Ohtsuki, M.; Hoshino, Y. FTY720, a Novel Immunosuppressant, Induces Sequestration of Circulating Mature Lymphocytes by Acceleration of Lymphocyte Homing in Rats, I. FTY720 Selectively Decreases the Number of Circulating Mature Lymphocytes by Acceleration of Lymphocyte Homing. J. Immunol. 1998, 160, 5037-5044.
39. Chiba, K.; Yanagawa, Y.; Masubuchi, Y.; Kataoka, H.; Kawaguchi, T.; Ohtsuki, M.; Hoshino, Y. FTY720, a Novel Immunosuppressant, Induces Sequestration of Circulating Mature Lymphocytes by Acceleration of Lymphocyte Homing in Rats, II. FTY720 Prolongs Skin Allograft Survival by Decreasing T Cell Infiltration into Grafts But Not Cytokine Production in vivo. J. Immunol. 1998, 160, 5493-5499.
40. Chiba, K.; Yanagawa, Y.; Kataoka, H.; Kawaguchi, T.; Ohtsuki, M.; Hoshino, Y. FTY720, a Novel Immunosuppressant, Induces Sequestration of Circulating Lymphocytes by Acceleration of Lymphocyte Homing. Transplant. Proc. 1999, 31, 1230-1233.
41. Dorsch, S. E.; Roser, B. A Quantitative Lymph Node Weight Assay for Allogeneic Interactions in the Rat. AJEBAK 1974, 52, 253-264.