Antihyperuricemic effects of thiadiazolopyrimidin-5-one analogues in oxonate treated rats

European Journal of Pharmacology

Volumn 776, Issue , 2016, Pages 99-105

  Sathisha, Kadanuru R ^a   Gopal, Shubha ^a   Rangappa, Kanchugarakoppal S ^a  

^a UNIVERSITY OF MYSORE   (India)

Author keywords

Gout; Hyperuricemia; Potassium oxonate; Thiadiazolopyrimidin 5 one analogues; Xanthine oxidase

Indexed keywords

7 METHYL 2 (PHENOXYMETHYL) 5H[1,3,4]THIADIAZOLO[3,2 A]PYRIMIDIN 5 ONE DERIVATIVE; ALLOPURINOL; ANTIGOUT AGENT; CREATININE; OTERACIL POTASSIUM; PYRIMIDINE DERIVATIVE; THIADIAZOLOPYRIMIDIN 5 ONE DERIVATIVE; UNCLASSIFIED DRUG; URIC ACID; XANTHINE OXIDASE INHIBITOR; [2 [[4 CHLORO 3 METHYLPHENOXY]METHYL] 7 METHYL 5H [1,3,4]THIADIAZOLO[3,2 A]PYRIMIDIN 5 ONE]; [2 [[4 CHLOROPHENOXY]METHYL] 7 METHYL 5H [1,3,4]THIADIAZOLO[3,2 A]PYRIMIDIN 5 ONE]; [2 [[4 METHOXYPHENOXY]METHYL] 7 METHYL 5H [1,3,4]THIADIAZOLO[3,2 A]PYRIMIDIN 5 ONE]; ENZYME INHIBITOR; OTERACIL; THIADIAZOLE DERIVATIVE; XANTHINE OXIDASE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIHYPERURICEMIC EFFECT; ARTICLE; CONTROLLED STUDY; CREATININE BLOOD LEVEL; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; HISTOPATHOLOGY; HYPERURICEMIA; KIDNEY NECROSIS; LIVER NECROSIS; MALE; MOLECULAR DOCKING; NONHUMAN; PRIORITY JOURNAL; RAT; URIC ACID BLOOD LEVEL; ANIMAL; BLOOD; CHEMICALLY INDUCED; CHEMISTRY; DRUG EFFECTS; ENZYME ACTIVE SITE; ENZYMOLOGY; KIDNEY; LIVER; METABOLISM; PATHOLOGY; WISTAR RAT;

ANIMALS; CATALYTIC DOMAIN; CREATININE; ENZYME INHIBITORS; HYPERURICEMIA; KIDNEY; LIVER; MALE; MOLECULAR DOCKING SIMULATION; OXONIC ACID; RATS; RATS, WISTAR; THIADIAZOLES; URIC ACID; XANTHINE OXIDASE;

EID: 84960878348     PISSN: 00142999     EISSN: 18790712     Source Type: Journal    
DOI: 10.1016/j.ejphar.2016.02.039     Document Type: Article

References (50)

1. F. Bonomini, S. Tengattini, A. Fibiano, R. Bianchi, and R. Rezzani Atherosclerosis and oxidative stress Histol. Histopathol. 23 2008 381 390
2. C. B-Rao, A. Kulkarni-Almeida, K.V. Katkar, S. Khanna, U. Ghosh, A. Keche, P. Shah, A. Srivastava, V. Korde, K.V. Nemmani, N.J. Deshmukh, A. Dixit, M.K. Brahma, U. Bahirat, L. Doshi, R. Sharma, and H. Sivaramakrishnan Identification of novel isocytosine derivatives as xanthine oxidase inhibitors from a set of virtual screening hits Biorgan. Med. Chem. 20 2012 2930 2939
3. K. Chih-Yi, K. Erl-Shyh, C. Kuei-Chuan, L. Huei-Jane, H. Tsai-Feng, and W. Chau-Jong Hibiscus sabdariffa L. extracts reduce serum Uric acid levels oxonate-induced rats J. Funct. Foods 4 2012 375 381
4. H.K. Choi, K. Atkinson, E.W. Karlson, W. Willett, and G. Curhan Purine-rich foods, dairy and protein intake, and the risk of gout in men N. Engl. J. Med. 350 2004 1093 1103
5. H.K. Choi, D.B. Mount, A.M. Reginato, American College of Physicians, and American Physiological Society Pathogenesis of gout Ann. Intern. Med. 143 2005 499 516
6. H.K. Choi, and E.S. Ford Prevalence of the metabolic syndrome in individuals with hyperuricemia Am. J. Med. 120 2007 442 447
7. N. Dalbeth, and A. So Hyperuricaemia and gout: state of the art and future perspectives Ann. Rheum. Dis. 69 2010 1738 1743
8. H. Duskin-Bitan, E. Cohen, E. Goldberg, T. Shochat, A. Levi, and M. Garty The degree of asymptomatic hyperuricemia and the risk of gout. A retrospective analysis of a large cohort Clin. Rheumatol. 33 2014 549 553
9. B.T. Emmerson The management of gout N. Engl. J. Med. 334 1996 445 451
10. A. Fukunari, K. Okamoto, T. Nishino, B.T. Eger, E.F. Pai, M. Kamezawa, I. Yamada, and N. Kato Y-700 [1-[3-Cyano-4-(2,2-dimethylpropoxy)phenyl]-1H-pyrazole-4-carboxylic acid]: a potent xanthine oxidoreductase inhibitor with hepatic excretion J. Pharmacol. Exp. Ther. 311 2004 519 528
11. S. Gupta, L.M. Rodrigues, A.P. Esteves, A.M. Oliveira-campos, M.S. Nascimento, N. Nazareth, H. Cidade, M.P. Neves, E. Fernandes, M. Pinto, N.M. Cerqueira, and N. Bras Synthesis of N-aryl-5-amino-4-cyanopyrazole derivatives as potent xanthine oxidase inhibitors Eur. J. Med. Chem. 43 2008 771 780
12. P.I. Hair, P.L. McCormack, and G.M. Keating Febuxostat Drugs 68 2008 1865 1874
13. J.F. Hsieh, S.H. Wu, Y.L. Yang, K.F. Choong, and S.T. Chen The screening and characterization of 6-aminopurine-based xanthine oxidase inhibitors Biorgan. Med. Chem. 15 2007 3450 3456
14. J. Huang, S. Wang, M. Zhu, J. Chen, and X. Zhu Effects of genistein, apigenin, quercetin, rutin and astilbin on serum uric acid levels and xanthine oxidase activities in normal and hyperuricemic mice Food Chem. Toxicol. 49 2011 1943 1947
15. S. Ishibuchi, H. Morimoto, T. Oe, T. Ikebe, H. Inone, A. Fukunari, M. Kamezawa, I. Yamada, and Y. Naka Synthesis and structure-activity relationships of 1-Phenylpyrazoles as xanthine oxidase inhibitors Biorgan. Med. Chem. Lett. 11 2001 879 882
16. R.J. Johnson, M.S. Segal, T. Srinivas, A. Ejaz, W. Mu, C. Roncal, L.G. Sanchez-Lozada, M. Gersch, B. Rodriguez-Iturbe, D.H. Kang, and J.H. Acosta Essential hypertension, progressive renal disease, and uric acid: a pathogenetic link? J. Am. Soc. Nephrol. 16 2005 1909 1919
17. R.S. Kadam, and K.R. Iyer Isolation of different animal liver xathine oxidase containing fractions and determination of kinetic parameters for xanthine Indian J. Pharm. Sci. 69 2007 41 45
18. J. Kanellis, S. Watanabe, J.H. Li, D.H. Kang, P. Li, and T. Nakagawa Uric acid stimulates monocyte chemoattractant protein-1 production in vascular smooth muscle cells via mitogen-activated protein kinase and cyclooxygenase-2 Hypertension 41 2003 1287 1293
19. C.O. Kappe Biologically active dihydropyrimidones of the Biginelli-Type A literature survey Eur. J. Med. Chem. 35 2000 1043 1052
20. I.H. Krakoff Use of allopurinol in preventing hyperuricemia in leukemia and lymphoma Cancer 19 1966 1489 1496
21. H.M. Kramer, and G. Curhan The association between gout and nephrolithiasis: the national health and nutrition examination survey III. 1988-1994 Am. J. Kidney Dis. 40 2002 37 42
22. V.P. Krivonogov, G.A. Tolstikov, and Yu.I. Murinov Synthesis and antioxidant activity of pyrimidine acyclonucleosides Khim-Farm. Zh. 27 1983 41 44
23. V.P. Krivonogov, G.A. Tolstikov, and Yu.I. Murinov Synthesis and study of immunotropic and anti-inflammatory activity of some pyrimidine derivatives part:V Khim-Farm. Zh. 31 1997 24 27
24. R. Kumar, Darpan., S. Sharma, and R. Singh Xanthine oxidase inhibitors: a patent survey Expert. Opin. Ther. Pat. 21 2011 1071 1108
25. A.S. Lewis, L. Murphy, C. Mccalla, M. Fleary, and S. Purcell Inhibition of mammalian xanthine oxidase by folate compounds and amethopterin J. Biol. Chem. 259 1984 12 15
26. C.M. Lin, C.S. Chen, C.T. Chen, Y.C. Liang, and J.K. Lin Molecular modeling of flavonoids that inhibits xanthine oxidase Biochem. Biophys. Res. Commun. 294 2002 167 172
27. K.C. Lin, H.Y. Lin, and P. Chou Community based epidemiological study on hyperuricemia and gout in Kin-Hu, Kinmen J. Rheumatol. 27 2000 1045 1050
28. X. Liu, R. Chen, Y. Shang, B. Jiao, and C. Huang Lithospermic acid as a novel xanthine oxidase inhibitor has anti-inflammatory and hypouricemic effects in rats Chem. Biol. Interact. 176 2008 137 142
29. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall Protein measurement with the folin phenol reagent J. Biol. Chem. 193 1951 265 275
30. N. Masuoka, and I. Kubo Characterization of xanthine oxidase inhibition by anacardic acids Biochim. Biophys. Acta 1688 2004 245 249
31. V.A. Myshkin, E.G. Khaibullina, and E.K. Alekhin Synthesis and antioxidant activity of pyrimidine acyclonucleosides Zdr. Bashkort 25 1994 411 413
32. K. Nepali, A. Agarwal, S. Sapra, V. Mittal, R. Kumar, U.C. Banerjee, M.K. Gupta, N.K. Satti, O.P. Suri, and K.L. Dhar N-(1,3-Diaryl-3-oxopropyl)amides as a new template for xanthine oxidase inhibitors Biorgan. Med. Chem. 19 2011 5569 5576
33. K. Nepali, G. Singh, A. Turan, A. Agarwal, S. Sapra, R. Kumar, U.C. Banerjee, P.K. Verma, N.K. Satti, M.K. Gupta, O.P. Suri, and K.L. Dhar A rational approach for the design and synthesis of 1-acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles as a new class of potential non-purine xanthine oxidase inhibitors Biorgan. Med. Chem. 19 2011 1950 1958
34. Y. Niu, H. Zhu, J. Liu, H. Fan, L. Sun, W. Lu, X. Liu, and L. Li 3,5,2',4'-Tetrahydroxychalcone, a new non-purine xanthine oxidase inhibitor Chem. Biol. Interact. 189 2011 161 166
35. K. Oettl, and G. Reibnegger Pteridines as inhibitors of xanthine oxidase: structural requirements Biochim. Biophys. Acta 1430 1999 387 395
36. K. Okamoto Inhibitors of xanthine oxidoreductase Nihon Rinsho 66 2008 748 753
37. A.E. Rashad, A.E. Mahmoud, and M.M. Ali Synthesis and anticancer effects of some novel pyrazolo[3,4-d]pyrimidine derivatives by generating reactive oxygen species in human breast adenocarcinoma cells Eur. J. Med. Chem. 46 2011 1019 1026
38. M. Riegersperger, A. Covic, and D. Goldsmith Allopurinol, uric acid, and oxidative stress in cardiorenal disease Int. Urol. Nephrol. 43 2011 441 449
39. K.R. Sathisha, S.A. Khanum, J.N. Chandra, F. Ayisha, S. Balaji, G.K. Marathe, S. Gopal, and K.S. Rangappa Synthesis and xanthine oxidase inhibitory activity of 7-methyl-2-(phenoxymethyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one derivatives Biorgan. Med. Chem. 19 2011 211 220
40. T. Sato, N. Ashizawa, K. Matsumoto, T. Iwanaga, H. Nakamura, T. Inoue, and O. Nagata Discovery of 3-(2-cyano-4-pyridyl)-5-(4-pyridyl)-1,2,4-triazole, FYX-051-a xanthine oxidoreductase inhibitor for the treatment of hyperuricemia [corrected] Biorgan. Med. Chem. Lett. 19 2009 6225 6229
41. L. Shen, and H.F. Ji Insights into the inhibition of xanthine oxidase by curcumin Biorgan. Med. Chem. Lett. 19 2009 5990 5993
42. T. Shimato, N. Ashizawa, K. Matzumoto, T. Nakazawa, and O. Nagata Simultaneous treatment with citrate prevents nephropathy induced by FYX-051, a xanthine oxidoreductase inhibitor, in rats Toxicol. Sci. 87 2005 267 276
43. R.A. Short, and K.R. Tuttle Clinical evidence for the influence of uric acid on hypertension, cardiovascular disease, and kidney disease: a statistical modeling perspective Semin. Nephrol. 25 2005 25 31
44. J. Sundstrom, L. Sullivan, R.B. D'Agostino, D. Levy, W.B. Kannel, and R.S. Vasan Relation of serum uric acid to longitudinal blood pressure tracking and hypertension incidence Hypertension 45 2005 28 33
45. M. Tomita, S. Mizuno, H. Yamanaka, Y. Hosoda, K. Sakuma, Y. Matuoka, M. Odaka, M. Yamaguchi, H. Yosida, H. Morisawa, and T. Murayama Does Hyperuricemia effect mortality? A prospective cohort study of Japanese male workers J. Epidemiol. 10 2000 403 409
46. 1 convenient and general synthesis of 3-substituted 7H-pyrazolo[4,3-e]-1,2,4-triazolo[4,3-c]pyrimidin-5(6H)-ones as a new class of potential xanthine oxidase inhibitors J. Chem. Soc. Park. Trans. 1 2000 33 42
47. S.L. Wallach The side effects of allopurinol Hosp. Pract. 33 1998 22
48. Y. Wang, J.X. Zhu, L.D. Kong, C. Yang, C.H. Cheng, and X. Zhang Administration of procyanidins from grape seeds reduces serum uric acid levels and decreases hepatic xanthine dehydrogenase/oxidase activities in oxonate-treated mice Basic. Clin. Pharmacol. Toxicol. 94 2004 232 237
49. S. Wang, J. Yan, J. Wang, J. Chen, T. Zhang, Y. Zhao, and M. Xue Synthesis of some 5-phenylisoxazole-3-carboxylic acid derivatives as potent xanthine oxidase inhibitors Eur. J. Med. Chem. 45 2010 2663 2670
50. J.X. Zhu, Y. Wang, L.D. Kong, C. Yang, and X.J. Zhang Effects of biota orientalis extract and its flavonoid constituents, quercetin and rutin on serum uric acid levels in oxonate-induced mice and xanthine dehydrogenase and xanthine oxidase activities in mouse liver J. Ethnopharmacol. 93 2004 133 140