Efficient syntheses of a series of trehalose dimycolate (TDM)/trehalose dicorynomycolate (TDCM) analogues and their interleukin-6 level enhancement activity in mice sera

Journal of Organic Chemistry

Volumn 72, Issue 5, 2007, Pages 1627-1633

  Nishizawa, Mugio ^a   Yamamoto, Hirofumi ^a   Imagawa, Hiroshi ^a   Barbier Chassefière, Véronique ^b   Petit, Emmanuel ^b   Azuma, Ichiro ^c   Papy Garcia, Dulce ^b  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^b Universite de Paris 12 Val de Marne ^*  (France)

^c HOKKAIDO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IMMUNOADJUVANT ACTIVITY; MYCOBACTERIUM TUBERCULOSIS; TREHALOSE DICORYNOMYCOLATE (TDCM); TREHALOSE DIMYCOLATE (TDM);

CELLS; DISEASES; LIPIDS; SYNTHESIS (CHEMICAL); TOXICITY; TUMORS;

AROMATIC COMPOUNDS;

CORD FACTOR; IMMUNOLOGICAL ADJUVANT; INTERLEUKIN 6; MYCOLIC ACID; TREHALOSE DICORYNOMYCOLATE; UNCLASSIFIED DRUG;

ALKYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CYTOKINE PRODUCTION; INHIBITION KINETICS; LUNG METASTASIS; MYCOBACTERIUM TUBERCULOSIS; REDUCTION KINETICS; SERODIAGNOSIS; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANIMALS; CARBOHYDRATE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CORD FACTORS; INTERLEUKIN-6; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICE; MOLECULAR SEQUENCE DATA; MYCOBACTERIUM TUBERCULOSIS; STIMULATION, CHEMICAL; TREHALOSE;

EID: 33847637118     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062018j     Document Type: Article

References (36)

1. Hirano, T.; Yasukawa, K.; Harada, H.; Taga, T.; Watanabe, Y.; Matsuda, T.; Kashiwamura, S.; Nakajima, K.; Koyama, K.; Iwamatsu, A.; Tsunasawa, S.; Sakiyama, F.; Matsui, H.; Takahara, Y.; Taniguchi, T.; Kitamoto, T. Nature 1986, 324, 73-76.
2. Hirano, T. International Review of Immunology; 1998; Vol. 16, pp 249-284.
3. (a) Ito, H. Curr. Drug Targets: Inflammation Allergy 2003, 2, 125-130.
4. (b) Matsumoto, T. Rinaho Byori 1999, 47, 494-500.
5. (a) Lowe, G. D. Ann. Periodontol. 2000, 6, 1-8.
6. (b) Volante, E.; Moretti, S.; Pisani, F.; Bevilacqua, G. J. Matern. Fetal Neonat. Med. 2004, 16, 13-16.
7. Riedel, F. Anticancer Res. 2005, 25, 2761-2764.
8. Nishino, N. Autoimmunity 2005, 38, 359-367.
9. Spellman, K.; Burns, J.; Nichols, D.; Winters, N.; Ottersberg, S.; Tenborg, M. Altern. Med. Rev. 2006, 11, 128-150.
10. (a) Bloch, H. J. Exp. Med. 1950, 91, 197-217.
11. (b) Noll, H.; Bloch, H.; Asselineau, J.; Lederer, E. Biochim. Biophys. Acta 1956, 20, 299-399.
12. Ryll, R.; Kumazawa, Y.; Yano, I. Microbiol. Immunol. 2001, 45, 801-811.
13. Azuma, I.; Yamamura, Y. J. Biochem 1962, 52, 82-91.
14. Numata, F.; Nishimura, K.; Ishida, H.; Ukei, S.; Tone, Y.; Ichihara, C.; Saiki, I.; Sekikawa, I.; Azuma, I. Chem. Pharm. Bull. 1985, 33, 4544-4555.
15. (a) Ioneda, T.; Lenz, M.; Pudles, J. Biochem. Biophys. Res. Commun. 1963, 13, 110-114.
16. (b) Senn, M.; Ioneda, T.; Pudles, J.; Lederer, E. Eur. J. Biochem. 1967, 1, 353-356.
17. (c) Puzo, G.; Tissie, G.; Aurelle, H.; Lacave, C.; Prome, J. C. Eur. J. Biochem. 1979, 98, 99-105.
18. Datta, A. K.; Takayama, K. Carbohydr. Res. 1993, 245, 151-158.
19. (a) Tocanne, J.-F.; Asselineau, C. Bull. Soc. Chim. Fr. 1968, 4519-4525.
20. (b) Kitano, Y.; Kobayashi, Y.; Sato, F. J. Chem. Soc., Chem. Commun. 1985, 498-499.
21. (c) Utaka, M.; Higashi, H.; Takeda, A. J. Chem. Soc., Chem. Commun. 1987, 1368-1369.
22. Nishizawa, M.; Minagawa, R.; García, D. M.; Hatakeyama, S.; Yamada, H. Tetrahedron Lett. 1994, 35, 5891-5894.
23. Nishizawa, M.; García, D. M.; Minagawa, R.; Noguchi, Y.; Imagawa, H.; Yamada, H.; Watanabe, R.; Yoo, Y. C.; Azuma, I. Synlett 1996, 452-454.
24. Watanabe, R.; Yoo, Y. C.; Hata, K.; Motobe, M.; Koike, Y.; Nishizawa, M.; García, D. M.; Noguchi, Y.; Imagawa, H.; Yamada, H.; Azuma, I. Vaccine 1999, 17, 1484-1492.
25. Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856-5858.
26. (a) Frater, G. Helv. Chim. Acta 1979, 62, 2825-2828.
27. (b) Wallace, G. A.; Heathcock, C. H. J. Org. Chem. 2001, 66, 450-454.
28. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
29. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
30. Hatakeyama, S.; Mori, H.; Kitano, K.; Yamada, H.; Nishizawa, M. Tetrahedron Lett. 1994, 35, 4367-4370. When the reaction was carried out at 0 °C or at room temperature, cleavage of the tert-butyl ester group also took place. See also ref 24.
31. TMSOTf-catalyzed cleavage of prenyl ester was developed recently in our group, and the same procedure was applied for the cleavage of tert-butyl ester. Nishizawa, M.; Yamamoto, H.; Seo, K.; Imagawa, H.; Sugihara, T. Org. Lett. 2002, 4, 1947-1949.
32. Imagawa, H.; Tsuchihashi, T.; Singh, R. K.; Yamamoto, H.; Sugihara, T.; Nishizawa, M. Org. Lett. 2003, 5, 153-155.
33. Bodem, E. P.; Keck, G. E. J. Org. Chem. 1985, 50, 2394-2395.
34. (a) Rondinone, C. M. Endocrine 2006, 29, 81-90.
35. (b) Hu, Y.; Sun, H.; Drake, J.; Kittrell, F.; Abba, M. C.; Deng, L.; Gaddis, S.; Sahin, A.; Baggerly, K.; Medina, D.; Aldaz, C. M. Cancer Res. 2004, 64, 7748-7755.
36. Vormittag, R.; Hsieh, K.; Kaider, A.; Minar, E.; Bialonczyk, C.; Hirschl, M.; Mannhalter, C.; Pabinger, I. Thromb Haemostasis 2006, 95, 802-806.