Synthesis and biological evaluation of four stereoisomers of PDMP-analogue, N-(2-decylamino-3-hydroxy-3-phenylprop- 1-yl)-β-valienamine, and related compounds

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 14, 1997, Pages 1915-1920

  Ogawa, Seiichiro ^a   Mito, Tamami ^a   Taiji, Eiichi ^a   Jimbo, Masayuki ^b   Yamagishi, Kiwamu ^b   Inokuchi, Jin Ichi ^b  

^a KEIO UNIVERSITY   (Japan)

^b SEIKAGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CERAMIDE GLUCOSYLTRANSFERASE; GLUCOSYLCERAMIDASE; GLUCOSYLTRANSFERASE; SYNTHETASE; TRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0030744022     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00341-7     Document Type: Article

References (20)

1. Radin, N. S.; Shayman, J. A.; Inokuchi, J.-i. Adv. Lipid Res. 1993, 26, 183.
2. Inokuchi, J.-i.; Jimbo, M.; Momosaki, K.; Shimeno, H.; Nagamatsu, A.; Radin, N. S. Cancer Res. 1990, 50, 6731.
3. Kyogashima, M.; Inoue, M.; Seto, A.; Inokuchi, J.-i. Cancer Lett. 1996, 101, 25, and references cited therein.
4. Tsunoda, H.; Inokuchi, J.-i.; Yamagishi, K.; Ogawa, S. Liebigs Ann. Chem. 1995, 279.
5. Tsunoda, H.; Ogawa, S. Liebigs Ann. Chem. 1995, 267.
6. Ogawa, S.; Ashiura, M.; Uchida, C.; Watanabe, S.; Yamazaki, C.; Yamagishi, K.; Inokuchi, J.-i. Bioorg. Med. Chem. Lett. 1996, 6, 929.
7. Ogawa, S.; Uchida, C.; Shibata, Y. Carbohydr. Res. 1992, 223, 279.
8. 1H NMR spectral analyses, being consistent with the assigned structures.
9. 2,3b 5.9 Hz H-3b).
10. 3).
11. Oyamada, H.; Jimbo, M. Jpn. Pat. Appl. JP 59576 (1996).
12. 3) δ 9.14 (d, 1 H, J 8.1 Hz, NHDNP), 9.03 (d, 1 H, J 2.6 Hz) and 8.05 (dd, 1 H, J 2.6, 9.5 Hz) (DNP), 7.45-7.15 (m, 5 H, Ph), 6.75 (d, 1 H, J 9.5 Hz, DNP), 5.39 (s, 1 H, H-5a), 5.25 (d, 1 H, J 2.2 Hz, H-3′), 4.62 (d, 1 H, J 7.7 Hz, H-4), 4.48 (d, 1 H, J 13.9 Hz, H-6a), 4.16 (d, 1 H, J 14.7 Hz, H-6b), 4.07-3.96 (m, 1 H, H-2′), 3.74 (dd, 1 H, J 8.8, 8.1 Hz, H-3), 3.67-3.60 (m, 1 H, H-1), 3.46 (dd, 1 H, J 8.8, 9.2 Hz, H-2), 3.36(dd, 1 H, J 5.7, 13.0 Hz, H-1′a), 3.23 (dd, 1 H, J 4.0, 13.2 Hz, H-1′b), 1.38-1.38 (4 s, 12 H, 4 x Me).
13. +, 479.3121. Found: 479.3114.
14. 25 -45° (c= 0.84, MeOH).
15. The ease with which removal of the DNP protecting groups underwent in the presence of the basic resin seemed to be depend on the stereochemistry of C-2 and 3, the over-all yields of the free bases being largely influenced.
16. 22 -16° (c = 1.2, MeOH).
17. 3).
18. Ogawa, S.; Shibata, Y. J. Chem. Soc., Chem. Commun. 1988, 605; Shibata, Y.; Ogawa, S. Carbohydr. Res. 1989, 189, 309.
19. Ogawa, S.; Shibata, Y. J. Chem. Soc., Chem. Commun. 1988, 605; Shibata, Y.; Ogawa, S. Carbohydr. Res. 1989, 189, 309.
20. 4, and counted without removing the precipitated protein.