Synthesis and biological evaluation of novel aryl-2H-pyrazole derivatives as potent non-purine xanthine oxidase inhibitors

Chemical and Pharmaceutical Bulletin

Volumn 63, Issue 8, 2015, Pages 603-607

  Sun, Zhi Gang ^a   Zhou, Xiao Jing ^a   Zhu, Ming Li ^a   Ding, Wen Ze ^a   Li, Zhen ^a   Zhu, Hai Liang ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

Inhibitory; Pyrazole; Xanthine oxidase

Indexed keywords

1 [5 (BENZO[ D ][1,3]DIOXOL 5 YL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 2 (3,4 DIMETHOXYPHENYL)ETHAN 1 ONE; 1 [5 (BENZO[D][1,3] DIOXOL 5 YL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 2 (4 FLUORPHENYL)ETHAN 1 ONE; 1 [5 (BENZO[D][1,3]DIOXOL 5 YL) 3 (3,4 DIMETHOXYPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL] 2 (3,4,5 TRIMETHOXYPHENYL)ETHAN 1 ONE; 1 [5 (BENZO[D][1,3]DIOXOL 5 YL) 3 (3,4 DIMETHOXYPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL] 2 (4 METHOXYPHENYL)ETHAN 1 ONE; 1 [5 (BENZO[D][1,3]DIOXOL 5 YL) 3 (3,4 DIMETHOXYPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL] 2 PHENYLETHAN 1 ONE; 1 [5 (BENZO[D][1,3]DIOXOL 5 YL) 3 (4 BROMOPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL] 2 (PYRIDIN 3 YL)ETHAN 1 ONE; 1 [5 (BENZO[D][1,3]DIOXOL 5 YL) 3 (4 ETHOXYPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL] 2 (3,4,5 TRIMETHOXYPHENYL)ETHAN 1 ONE; 1 [5 (BENZO[D][1,3]DIOXOL 5 YL) 3 (4 METHOXYPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL] 2 (3,4 DIMETHOXYPHENYL)ETHAN 1 ONE; 1 [5 (BENZO[D][1,3]DIOXOL 5 YL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 2 (3 METHOXYPHENYL)ETHAN 1 ONE; 1 [5 (BENZO[D][1,3]DIOXOL 5 YL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 2 (4 BROMOPHENYL)ETHAN 1 ONE; 1 [5 (BENZO[D][1,3]DIOXOL 5 YL) 3 PHENYL 4,5 DIHYDRO 1H PYRAZOL 1 YL] 2 (4 CHLOROPHENYL)ETHAN 1 ONE; 1 [5 (BENZO[D][1,3]DIOXOL5 YL) 3 (3,4 DIMETHOXYPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL] 2 (4 BROMOPHENYL)ETHAN 1 ONE; ALLOPURINOL; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; XANTHINE OXIDASE; XANTHINE OXIDASE INHIBITOR; ENZYME INHIBITOR; PYRAZOLE;

ARTICLE; BIOASSAY; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVE SITE; GOUT; IN VITRO STUDY; MOLECULAR DOCKING; MOLECULAR MODEL; SCREENING; STRUCTURE ACTIVITY RELATION; ANIMAL; ANTAGONISTS AND INHIBITORS; BOVINE; CHEMISTRY; DRUG EFFECTS; METABOLISM; SYNTHESIS;

ANIMALS; CATALYTIC DOMAIN; CATTLE; ENZYME INHIBITORS; MOLECULAR DOCKING SIMULATION; PYRAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP; XANTHINE OXIDASE;

EID: 84940397193     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.c15-00282     Document Type: Article

References (17)

1. Borges F., Fernandes E., Roleira F., Curr. Med. Chem., 9, 195-217 (2002).
2. Ferrari A. M., Sgobba M., Gamberini M. C., Rastelli G., Eur. J. Med. Chem., 42, 1028-1031 (2007).
3. Hille R., Eur. J. Inorg. Chem., 2006, 1913-1926 (2006).
4. Pacher P., Nivorozhkin A., Szabó C., Pharmacol. Rev., 58, 87-114 (2006).
5. Biagi G., Giorgi I., Pacchini F., Livi O., Scartoni V., Il Farmaco, 56, 809-813 (2001).
6. Oettl K., Reibnegger G., Protein Structure and Molecular Enzymology, 1430, 387-395 (1999).
7. Nepali K., Agarwal A., Sapra S., Mittal V., Kumar R., Banerjee U. C., Gupta M. K., Satti N. K., Suri O. P., Dhar K. L., Bioorg. Med. Chem., 19, 5569-5576 (2011).
8. Ishibuchi S., Morimoto H., Oe T., Ikebe T., Inoue H., Fukunari A., Kamezawa M., Yamada I., Naka Y., Bioorg. Med. Chem. Lett., 11, 879-882 (2001).
9. Van Hoorn D. E., Nijveldt R. J., Van Leeuwen P. A., Hofman Z., M'Rabet L., De Bont D. B., Van Norren K., Eur. J. Pharmacol., 451, 111-118 (2002).
10. Okamoto K., Matsumoto K., Hille R., Eger B. T., Pai E. F., Nishino T., Proc. Natl. Acad. Sci. U. S. A., 101, 7931-7936 (2004).
11. Shen L., Ji H.-F., Bioorg. Med. Chem. Lett., 19, 5990-5993 (2009).
12. Liu X.-H., Ruan B.-F., Liu J.-X., Song B.-A., Jing L.-H., Li J., Yang Y., Zhu H.-L., Qi X.-B., Bioorg. Med. Chem. Lett., 21, 2916-2920 (2011).
13. Hayat F., Salahuddin A., Umar S., Azam A., Eur. J. Med. Chem., 45, 4669-4675 (2010).
14. Nepali K., Singh G., Turan A., Agarwal A., Sapra S., Kumar R., Banerjee U. C., Verma P. K., Satti N. K., Gupta M. K., Suri O. P., Dhar K. L., Bioorg. Med. Chem., 19, 1950-1958 (2011).
15. Luo Y., Zhang S., Qiu K.-M., Liu Z.-J., Yang Y.-S., Fu J., Zhong W.-Q., Zhu H.-L., Bioorg. Med. Chem. Lett., 23, 1091-1095 (2013).
16. Xu F., Zhao X., Yang L., Wang X., Zhao J., Molecules, 19, 13422-13431 (2014).
17. Enroth C., Eger B. T., Okamoto K., Nishino T., Nishino T., Pai E. F., Proc. Natl. Acad. Sci. U. S. A., 97, 10723-10728 (2000).