Novel aminopeptidase N inhibitors derived from 1,3,4-thiadiazole scaffold

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 14, 2008, Pages 6663-6668

  Tu, GuoGang ^a,b   Li, ShaoHua ^b   Huang, HuiMing ^b   Li, Gang ^b   Xiong, Fang ^b   Mai, Xi ^b   Zhu, HuaWei ^a   Kuang, BinHai ^b   Xu, Wen Fang ^a  

^a SHANDONG UNIVERSITY   (China)

^b NANCHANG UNIVERSITY   (China)

Author keywords

Aminopeptidase N; Enzyme inhibitors; Peptidomimetics

Indexed keywords

BESTATIN; MICROSOMAL AMINOPEPTIDASE; N [5 (4 BROMOPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(4 COUMAROYL)AMINO]PROPANAMIDE; N [5 (4 BROMOPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(4 METHOXYCINNAMOYL)AMINO]PROPANAMIDE; N [5 (4 BROMOPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(CINNAMOYL)AMINO]PROPANAMIDE; N [5 (4 CHLOROPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(4 COUMAROYL)AMINO]PROPANAMIDE; N [5 (4 CHLOROPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(4 METHOXYCINNAMOYL)AMINO]PROPANAMIDE; N [5 (4 CHLOROPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(CINNAMOYL)AMINO]PROPANAMIDE; N [5 (4 FLUOROPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(4 COUMAROYL)AMINO]PROPANAMIDE; N [5 (4 FLUOROPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(4 METHOXYCINNAMOYL)AMINO]PROPANAMIDE; N [5 (4 FLUOROPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(CINNAMOYL)AMINO]PROPANAMIDE; N [5 (4 METHOXYPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(4 COUMAROYL)AMINO]PROPANAMIDE; N [5 (4 METHOXYPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(CINNAMOYL)AMINO]PROPANAMIDE; N [5 (4 METHYLPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(4 COUMAROYL)AMINO]PROPANAMIDE; N [5 (4 METHYLPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(4 METHOXYCINNAMOYL)AMINO]PROPANAMIDE; N [5 (4 METHYLPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(CINNAMOYL)AMINO]PROPANAMIDE; N [5 (4 NITROROPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(4 COUMAROYL)AMINO]PROPANAMIDE; N [5 (4 NITROROPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(4 METHOXYCINNAMOYL)AMINO]PROPANAMIDE; N [5 (4 NITROROPHENYL) 1,3,4 THIADIAZOL 2 YL] 2 [(CINNAMOYL)AMINO]PROPANAMIDE; N [5 PHENYL 1,3,4 THIADIAZOL 2 YL] 2 [(4 COUMAROYL)AMINO]PROPANAMIDE; N [5 PHENYL 1,3,4 THIADIAZOL 2 YL] 2 [(4 METHOXYCINNAMOYL)AMINO]PROPANAMIDE; N [5 PHENYL 1,3,4 THIADIAZOL 2 YL] 2 [(CINNAMOYL)AMINO]PROPANAMIDE; THIADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INHIBITION; IC 50; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANGIOGENESIS INHIBITORS; ANTIGENS, CD13; BINDING SITES; DRUG SCREENING ASSAYS, ANTITUMOR; ESCHERICHIA COLI; MOLECULAR STRUCTURE; NEOPLASM PROTEINS; PROTEASE INHIBITORS; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP; THIADIAZOLES;

EID: 47349104618     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.05.081     Document Type: Article

References (31)

1. Riemann D., Kehlen A., and Langner J. Immunol. Today 20 (1999) 83
2. Hooper N.M. FEBS Lett. 354 (1994) 1
3. Delmas B., Gelfi J., L'Haridon R., Vogel L.K., Sjostrom H., Noren O., and Laude H. Nature 357 (1992) 417
4. Nakanishi K., Yaoi K., Nagino Y., Hara H., Kitami M., Atsumi S., Miura N., and Sato R. FEBS Lett. 519 (2002) 215
5. Yeager C.L., Ashmun R.A., Williams R.K., Cardellichio C.B., Shapiro L.H., Look A.T., and Holmes K.V. Nature 357 (1992) 420
6. Hattori A., and Tsujimoto M. Biol. Pharm. Bull. 27 (2004) 777
7. Irazusta J., Valdivia A., Fernandez D., Agirregoitia E., Ochoa C., and Casis L. J. Androl. 25 (2004) 733
8. Kanayama N., Kajiwara Y., Goto J., el Maradny E., Maehara K., Andou K., and Terao T. J. Leukocyte Biol. 57 (1995) 129
9. Larsen S.L., Pedersen L.O., Buus S., and Stryhn A. J. Exp. Med. 184 (1996) 183
10. Mitsui T., Nomura S., Itakura A., and Mizutani S. Biol. Pharm. Bull. 27 (2004) 768
11. Shipp M.A., and Look A.T. Blood 82 (1993) 1052
12. Pulido-Cejudo G., Conway B., Proulx P., Brown R., and Izaguirre C.A. Antiviral Res. 36 (1997) 167
13. Fujii H., Nakajima M., Saiki I., Yoneda J., Azuma I., and Tsuruo T. Clin. Exp. Metastasis 13 (1995) 337
14. Ishii K., Usui S., Sugimura Y., Yoshida S., Hioki T., Tatematsu M., Yamamoto H., and Hirano K. Int. J. Cancer 92 (2001) 49
15. Tomanek R.J., and Schatteman G.C. Anat. Rec. 261 (2000) 126
16. Bhagwat S.V., Lahdenranta J., Giordano R., Arap W., Pasqualini R., and Shapiro L.H. Blood 97 (2001) 652
17. Hashida H., Takabayashi A., Kanai M., Adachi M., Kondo K., Kohno N., Yamaoka Y., and Miyake M. Gastroenterology 122 (2002) 376
18. Sato Y. Biol. Pharm. Bull. 27 (2004) 5
19. Antczak C., De Meester I., and Bauvois B. Bioessays 23 (2001) 251
20. Lohn M., Mueller C., and Langner J. Leuk. Lymphoma 43 (2002) 407
21. Saiki I., Fujii H., Yoneda J., Abe F., Nakajima M., Tsuruo T., and Azuma I. Int. J. Cancer 54 (1993) 137
22. Becker J.W., Marcy A.I., Rokosz L.L., Axel M.G., Burbaum J.J., Fitzgerald P.M.D., Cameron P.M., Esser C.K., Hagmann W.K., Hermes J.D., and Springer J.P. Protein Sci. 4 (1995) 1966
23. Rzeski W., Matysiak J., and Kandefer-Szerszeń M. Bioorg. Med. Chem. 15 (2007) 3201
24. Akao Y., Maruyama H., Matsumoto K., Ohguchi K., Nishizawa K., Sakamoto T., Araki Y., Mishima S., and Nozawa Y. Biol. Pharm. Bull. 26 (2003) 1057
25. Foroumadi A., Daneshtalab M., and Shafiee A. Arzneimittel-Forschung 49 (1999) 1035
26. Levy M., and Palmer A.H. J. Biol. Chem. 146 (1942) 493
27. Song K.S., Ishikawa Y., Kobayashi S., Sankawa U., and Ebizuka Y. Phytochemistry 31 (1992) 823
28. Kim H., Burley S.K., and Lipscomb W.N. J. Mol. Biol. 230 (1993) 722
29. Wallace A.C., Laskowski R.A., and Thornton J.M. Protein Eng. 8 (1995) 127
30. Lejczak B., Kafarski P., and Zygmunt J. Biochemistry 28 (1989) 3549
31. Baragi V.M., Shaw B.J., Renkiewicz R.R., Kuipers P.J., Welgus H.G., Mathrubutham M., Cohen J.R., and Rao S.K. Matrix Biol. 19 (2000) 267