Synthesis and biological activities of neoechinulin A derivatives: New aspects of structure-activity relationships for neoechinulin A

Chemical and Pharmaceutical Bulletin

Volumn 56, Issue 12, 2008, Pages 1738-1743

  Kuramochi, Kouji ^a   Ohnishi, Kensuke ^a   Fujieda, Satoshi ^a   Nakajima, Mitsuhiro ^a   Saitoh, Yoshihiko ^a   Watanabe, Nobuo ^a   Takeuchi, Toshifumi ^a   Nakazaki, Atsuo ^a   Sugawara, Fumio ^a   Arai, Takao ^a   Kobayashi, Susumu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Antioxidant; Neoechinulin A; Reactive nitrogen species; Reactive oxygen species; Structure activity relationship

Indexed keywords

3 (4 MORPHOLINYL)SYDNONIMINE; 3 [(2 TERT BUTYL 1 METHOXYMETHYL 1H INDOL 3 YL)METHYLENE] 2,5 PIPERAZINEDIONE; 3 [2 (1,1 DIMETHYL 2 PROPENYL) 1H INDOL 3 YL]METHYL 2,5 PIPERAZINEDIONE; 3 [[2 (1,1 DIMETHYL 2 PROPENYL) 6 METHOXYMETHYLOXY 1H INDOL 3 YL]METHYLENE] 2,5 PIPERAZINEDIONE; 3 NITROTYROSINE; ELECTROPHILE; ETHYL 2 (TERT BUTYLOXYCARBONYLAMINO) 3 [2 (1,1 DIMETHYL 2 PROPENYL)1H INDOL 3 YL]ACRYLATE; INDOLE; INDOLE ALKALOID; MORPHOLINE DERIVATIVE; NEOECHINULIN A; NEOECHINULIN A DERIVATIVE; PEROXYNITRITE; PIPERAZINEDIONE; PREECHINULIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; BRAIN HOMOGENATE; CELL PROTECTION; CELL STRAIN; CELL VIABILITY; CHEMICAL BOND; CHEMICAL REACTION; CONTROLLED STUDY; CYTOPATHOGENIC EFFECT; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; LIPID PEROXIDATION; NITRATION; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIOXIDANTS; BRAIN CHEMISTRY; CELL SURVIVAL; INDICATORS AND REAGENTS; INDOLE ALKALOIDS; LIPID PEROXIDATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLSIDOMINE; NITRATES; PC12 CELLS; PEROXYNITROUS ACID; PIPERAZINES; PROTECTIVE AGENTS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; TYROSINE;

EID: 57349134405     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.56.1738     Document Type: Article

References (29)

1. Beckman J. S., Beckman T. W., Chen J., Marshall P. A., Freeman B. A., Proc. Natl. Acad. Sci. U.S.A., 87, 1620-1624 (1990).
2. Darley-Usmar V. M., Hogg N. O., Leary V. J., Wilson M. T., Moncada S., Free Radic. Res. Commun., 17, 9-20 (1992).
3. Salgo M. G., Bermudez E., Squadrito G. L., Pryor W. A., Arch. Biochem. Biophys., 322, 500-505 (1995).
4. Radi R., Beckman J. S., Bush K. M., Freeman B. A., Arch. Biochem. Biophys., 288, 481-487 (1991).
5. Ischiropoulos H., al-Mehdi A. B., FEBS Lett., 364, 279-282 (1995).
6. Van der Viiet A. O., Neill C. A., Halliwell B., Cross C. E., Kaur H., FEBS Lett., 39, 89-92 (1994).
7. Good P. F., Hsu A., Werner P., Perl D. P., Olanow C. W., J. Neuropathol. Exp. Neurol., 57, 338-342 (1998).
8. Smith M. A., Richey Harris P. L., Sayre L. M., Beckman J. S., Perry G., J. Neurosci., 17, 2653-2657 (1997).
9. Good P. F., Werner P., Hsu A., Olanow C. W., Perl D. P., Am. J. Pathol., 149, 1-28 (1996).
10. Maruyama K., Ohuchi T., Yoshida K., Shibata Y., Sugawara F., Arai T., J. Biochem., 136, 81-87 (2004).
11. Aoki T., Kamisuki S., Kimoto M., Ohnishi K., Takakusagi Y., Kuramochi K., Takeda Y., Nakazaki A., Kuroiwa K., Ohuchi T., Sugawara F., Arai T., Kobayashi S., Synlett, 677-680 (2006).
12. Kimoto K., Aoki T., Shibata Y., Kamisuki S., Sugawara F., Kuramochi K., Nakazaki A., Kobayashi S., Kuroiwa K., Watanabe N., Arai T., J. Antibiot., 60, 614-621 (2007).
13. Iritani K., Matsubara S., Utimoto K., Tetrahedron Lett., 29, 1799-1802 (1988).
14. Kanmera T., Lee S., Aoyagi H., Izumiya N., Int. J. Pept. Protein Res., 16, 280-290 (1980).
15. Slight racemization of the diketopiperazine might occur in the condensation of 9 with 10 and deprotection of the protecting groups. However, we prepared compound 2 by this straightforward approach since we found that no significant difference in the activity between (-)-1 and (+)-1.
16. Kuramochi K., Aoki S., Nakazaki A., Kamisuki S., Takeno M., Ohnishi K., Takeda Y., Kimoto K., Watanabe N., Kamakura T., Arai T., Sugawara F., Kobayashi S., Synthesis, in press.
17. Houghton E., Saxton J. E., J. Chem. Soc. (C), 1969, 1003-1012 (1969).
18. Allen C. M., Biochemisty, 11, 2154-2160 (1972).
19. Allen C. M., J. Am. Chem. Soc., 95, 2386-2387 (1973).
20. Hamasaki T., Nagayama K., Hatsuda Y., Agric. Biol. Chem., 40, 203-205 (1976).
21. Oikawa Y., Yoshioka T., Yonemitsu O., Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 21, 22-27 (1978).
22. Schkeryanz J. M., Woo J. C. G., Danishefsky S. J., J. Am. Chem. Soc., 117, 7025-7026 (1995).
23. Schkeryanz J. M., Woo J. C. G., Siliphaivanh P., Depew K. M., Danishefsky S. J., J. Am. Chem. Soc., 121, 11964-11975 (1999).
24. Tatsuta K., Mukai H., Mitsumoto K., J. Antibiot., 54, 105-108 (2001).
25. Nonoyama N., Oshima H., Shoda C., Suzuki H., Bull. Chem. Soc. Jpn., 74, 2385-2395 (2001).
26. Lee J. M., Johnson D. A., J. Biochem. Mol. Biol., 37, 139-143 (2004).
27. Itoh K., Tong K. I., Yamamoto M., Free Radic. Biol. Med., 36, 1208-1213 (2004).
28. Saito Y., Nishio K., Numakawa Y., Ogawa Y., Yoshida Y., Noguchi N., Niki E., J. Neurochem., 102, 1625-1634 (2007).
29. De Long M. J., Prochaska H. J., Talalay P., Proc. Natl. Acad. Sci. U.S.A., 83, 787-791 (1986).