Design, synthesis, and preliminary activity evaluation of novel peptidomimetics as aminopeptidase N/CD13 inhibitors

Archiv der Pharmazie

Volumn 344, Issue 8, 2011, Pages 494-504

  Li, Xun ^a   Wang, Junli ^a   Zhang, Lei ^a   Xu, Wenfang ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

Aminopeptidase N inhibitor; Antiproliferative activity; APN CD13; Peptidomimetics

Indexed keywords

4 (BENZYLOXY) N HYDROXY 1 (5 (HYDROXYAMINO) 5 OXO 2 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOYL)PYRROLIDINE 2 CARBOXAMIDE; 5 (1 METHOXY 1 OXO 3 PHENYLPROPAN 2 YLAMINO) 5 OXO 4 (3,4,5 TRIMETHOXY BENZAMIDO)PENTANOIC ACID; 5 (1 METHOXY 1 OXOBUTAN 2 YLAMINO) 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 (1 METHOXY 1 OXOHEXAN 2 YLAMINO) 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 (1 METHOXY 1 OXOPENTAN 2 YLAMINO) 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 (1 METHOXY 1 OXOPROPAN 2 YLAMINO) 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO) PENTANOIC ACID; 5 (2 METHOXY 2 OXOETHYLAMINO) 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 (3 HYDROXY 1 METHOXY 1 OXOPROPAN 2 YLAMINO) 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 [1 METHOXY 1 OXO 3 (PHENYLTHIO)PROPAN 2 YLAMINO] 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 [1 METHOXY 4 (METHYLTHIO) 1 OXOBUTAN 2 YLAMINO] 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 [3 (1H INDOL 3 YL) 1 METHOXY 1 OXOPROPAN 2 YLAMINO] 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 [3 (4 BROMOPHENYL) 1 METHOXY 1 OXOPROPAN 2 YLAMINO] 5 OXO 4 (3,4,5 TRIMETHOXY BENZAMIDO)PENTANOIC ACID; 5 [3 (4 CHLOROPHENYL) 1 METHOXY 1 OXOPROPAN 2 YLAMINO] 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 [3 (4 FLUOROPHENYL) 1 METHOXY 1 OXOPROPAN 2 YLAMINO] 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 [3 (4 HYDROXYPHENYL) 1 METHOXY 1 OXOPROPAN 2 YLAMINO] 5 OXO 4 (3,4,5 TRIMETHOXY BENZAMIDO)PENTANOIC ACID; 5 [3 [1 (BENZYLOXYCARBONYL) 1H IMIDAZOL 4 YL] 1 METHOXY 1 OXOPROPAN 2 YLAMINO] 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 [4 (BENZYLOXY) 2 (METHOXYCARBONYL)PYRROLIDIN 1 YL] 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 [5 (BENZYLOXYCARBONYL) 1 METHOXY 1 OXOPENTAN 2 YLAMINO] 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 [6 (BENZYLOXYCARBONYL) 1 METHOXY 1 OXOHEXAN 2 YLAMINO] 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 [6 (BENZYLOXYCARBONYL) 1 METHOXY 1 OXOHEXAN YLAMINO] 5 OXO 4 (3,4,5 TRIMETHOXYBENZAMIDO)PENTANOIC ACID; 5 OXO 5 (THIAZOL 2 YLAMINO) 4 (3,4,5 TRIHYDROXY BENZAMIDO)PENTANOIC ACID; 5 OXO 5 (THIAZOL 2 YLAMINO) 4 (3,4,5 TRIMETHOXY TRIMETHOXY BENZAMIDO)PENTANOIC ACID; BESTATIN; GELATINASE A; MICROSOMAL AMINOPEPTIDASE; N [5 (HYDROXYAMINO) 1 (2 (HYDROXYAMINO) 2 OXOETHYLAMINO 1,5 DIOXOPENTAN 2 YL] 3,4,5 TRIMETHOXYBENZAMIDE; PEPTIDOMIMETIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANTIGENS, CD13; DRUG DESIGN; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; PEPTIDOMIMETICS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80051516691     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.201100109     Document Type: Article

References (24)

1. H. Tsukamoto, K. Shibata, H. Kajiyama, M. Terauchi, A. Nawa, F. Kikkawa, BMC Cancer 2008, 8, 74.
2. M. Wickström, R. Larsson, P. Nygren, J. Gullbo, Cancer Sci. 2011, 102, 501-508.
3. S. V. Bhagwat, N. Petrovic, Y. Okamoto, L. H. Shapiro, Blood 2003, 101, 1818-1826.
4. Y. Luan, C. Ma, Z. Sui, X. Wang, J. Feng, N. Liu, F. Jing, Y. Wang, M. Li, H. Fang, W. Xu, Med. Chem. 2011, 7, 32-36.
5. X. P. Zhang, W. F. Xu, Curr. Med. Chem. 2008, 15, 2850-2865.
6. W. Xu, Q. Li, Curr. Med. Chem. Anticancer Agents 2005, 5, 281-301.
7. M. R. Jia, T. Wei, W. F. Xu, Front Neurosci. 2010, 4, 50.
8. M. B. Harbut, G. Velmourougane, G. Reiss, R. Chandramohanadas, D. C. Greenbaum, Bioorg. Med. Chem. Lett. 2008, 18, 5932-5936.
9. K. Ito, Y. Nakajima, Y. Onohara, M. Takeo, K. Nakashima, F. Matsubara, T. Ito, T. Yoshimoto, J. Biol. Chem. 2006, 281, 33664-33676.
10. A. Addlagatta, L. Gay, B. W. Matthews, Proc. Natl. Acad. Sci. USA 2006, 103, 13339-13344.
11. X. Li, J. Wang, J. Li, J. Wu, Y. Li, H. Zhu, R. Fan, W. Xu, Bioorg. Med. Chem. 2009, 17, 3053-3060.
12. X. Li, Y. Wang, J. Wu, Y. Li, Q. Wang, W. Xu, Bioorg. Med. Chem. 2009, 17, 3061-3071.
13. X. Li, J. L. Wang, W. F. Xu, J. Chem. Res. 2005, 2, 94-95.
14. S. W. Tang, T. C. Yang, W. C. Lin, W. H. Chang, C. C. Wang, M. K. Lai, J. Y. Lin, Carcinogenesis 2011, 32, 138-145.
15. Y. L. Liu, W. T. Bai, W. Luo, D. X. Zhang, Y. Yan, Z. K. Xu, F. L. Zhang, Tumour Biol. 2011, 32, 99-105.
16. J. Gabrilovac, D. Breljak, B. ÄŒupiÄ, Int. Immunopharmacol. 2008, 8, 613-623.
17. SYBYL 6.91, Tripos Associates, St. Louis, MO 2003.
18. N. M. Hooper, FEBS Lett. 1994, 354, 1-6.
19. Y. Feng, J. J. Likos, L. Zhu, H. Woodward, G. Munie, J. J. McDonald, A. M. Stevens, C. P. Howard, G. A. De Crescenzo, D. Welsch, H. S. Shieh, W. C. Stallings, Biochim. Biophys. Acta 2002, 1598, 10-23.
20. B. Lejczak, P. Kafarski, J. Zygmunt, Biochemistry 1989, 28, 3549-3555.
21. V. M. Baragi, B. J. Shaw, R. R. Renkiewicz, P. J. Kuipers, H. G. Welgus, M. Mathrubutham, J. R. Cohen, S. K. Rao, Matrix Biol. 2000, 19, 267-273.
22. GALAHADTM, Tripos Inc, St. Louis, MI, USA.
23. N. J. Richmond, C. A. Abrams, P. R. Wolohan, E. Abrahamian, P. Willett, R. D. Clark, J. Comput.-Aided Mol. Des. 2006, 20, 567-587.
24. H. M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T. N. Bhat, H. Weissig, I. N. Shindyalov, P. E. Bourne, Nucleic Acids Res. 2000, 28, 235-242.