Design, synthesis and preliminary evaluation of novel pyrrolidine derivatives as matrix metalloproteinase inhibitors

European Journal of Medicinal Chemistry

Volumn 43, Issue 10, 2008, Pages 2130-2139

  Cheng, Xian Chao ^a   Wang, Qiang ^a   Fang, Hao ^a   Tang, Wei ^b   Xu, Wen Fang ^a  

^a SHANDONG UNIVERSITY   (China)

^b University of Tokyo   (Japan)

Author keywords

IC50; MMP 2 inhibitors; Pyrrolidine derivatives; Synthesis

Indexed keywords

1 ACETYL 4 (CINNAMAMIDO) N HYDROXYPYRROLIDINE 2 CARBOXAMIDE; 4 (3,4,5 TRIMETHOXYBENZAMIDO) 1 ACETYL N HYDROXYPYRROLIDINE 2 CARBOXAMIDE; ENZYME INHIBITOR; GELATINASE INHIBITOR; HYDROXAMIC ACID DERIVATIVE; LY 52; MATRIX METALLOPROTEINASE INHIBITOR; MICROSOMAL AMINOPEPTIDASE; N [5 (HYDROXYCARBAMOYL) 1 ACETYLPYRROLIDIN 3 YL]NICOTINAMIDE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

AMINO ACID SEQUENCE; ANTIGENS, CD13; DRUG DESIGN; ENZYME INHIBITORS; MATRIX METALLOPROTEINASE 2; MATRIX METALLOPROTEINASES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRROLIDINES;

EID: 53149148170     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2007.12.020     Document Type: Article

References (18)

1. Murphy G.J.P., Murphy G., and Reynolds J.J. FEBS Lett. 289 1 (1991) 4-7
2. Bjorklund M., and Koivunen E. Biochim. Biophys. Acta 1755 (2005) 37-69
3. Polette M., Nawrocki-Raby B., Gilles C., Clavel C., and Birembaut P. Crit. Rev. Oncol. Hematol. 49 (2004) 179-186
4. Verma R.P., and Hansch C. Bioorg. Med. Chem. 15 (2007) 2223-2268
5. Nagase H., Visse R., and Murphy G. Cardiovasc. Res. 69 (2006) 562-573
6. Kontogiorgis C.A., Papaioannou P., and Hadjipavlou-Litina D.J. Curr. Med. Chem. 12 (2005) 339-355
7. Fisher J.F., and Mobashery S. Cancer Metastasis Rev. 25 (2006) 115-136
8. Li Y.L., and Xu W.F. Bioorg. Med. Chem. 12 (2004) 5171-5180
9. Qu X., Yuan Y., Xu W., Chen M., Cui S., Meng H., Li Y., Makuuchi M., Nakata M., and Tang W. Anticancer Res. 26 5A (2006) 3573-3578
10. Jordis U., Sauter F., and Siddiqi S.M. Indian J. Chem. 28B (1989) 294-296
11. Kemp D.S., Curran T.P., Davis W.M., Boyd J.G., and Muendel C. J. Org. Chem. 56 (1991) 6672-6682
12. Meena, and Kumar V.A. Bioorg. Med. Chem. 11 (2003) 3393-3399
13. Tsuzuki Y., Chiba K., and Hino K. Tetrahedron: Asymmetry 12 (2001) 1793-1799
14. Younes S., Labssita Y., Baziard-Mouysset G., Payard M., Rettori M.C., Renard P., Pfeiffer B., and Caignard D.H. Eur. J. Med. Chem. 35 (2000) 107-121
15. Pikul S., Dunham K.L.M., Almstead N.G., De B., Natchus M.G., Anastasio M.V., McPhail S.J., Snider C.E., Taiwo Y.O., Chen L., Dunaway C.M., Gu F., and Mieling G.E. J. Med. Chem. 42 (1999) 87-94
16. 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) 267-273
17. Lejczak B., Kafarski P., and Zygmunt J. Biochemistry 28 8 (1989) 3549-3555
18. Xu W., and Li Q. Curr. Med. Chem. Anti-Cancer Agents 5 (2005) 281-301