Synthesis and biological study of 3-butyl-1-(2,6-dichlorophenyl)-1H-[1,2,4] triazol-5(4H)-one derivatives as anti-hypertension drugs

Letters in Drug Design and Discovery

Volumn 7, Issue 1, 2010, Pages 18-22

  Zhang, Yanchun ^a   Zhou, Jinpei ^a   Pan, Weihong ^a   Wu, Xiaoming ^a   Wang, Shuai ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Anti hypertension; AT1 antagonist; Nitric oxide donating; Synthesis

Indexed keywords

3 (NITROOXY)PROPYL 4' [[3 BUTYL 1 (2,6 DICHLOROPHENYL) 5 OXO 1H 1,2,4 TRIAZOL 4(5H) YL]METHYL]BIPHENYL 2 CARBOXYLATE; 4 [3 [4' [[3 BUTYL 1 (2,6 DICHLOROPHENYL) 5 OXO 1H 1,2,4 TRIAZOL 4(5H) YL]METHYL]BIPHENYLCARBONYLOXY]BUTOXY] 3 (PHENYLSULFONYL)[1,2,5]OXADIAZOLE 2 OXIDE; 4 [3 [4' [[3 BUTYL 1 (2,6 DICHLOROPHENYL) 5 OXO 1H 1,2,4 TRIAZOL 4(5H) YL]METHYL]BIPHENYLCARBONYLOXY]PROPOXY] 3 (PHENYLSULFONYL)[1,2,5]OXADIAZOLE 2 OXIDE; 4 [4 [4' [[3 BUTYL 1 (2,6 DICHLOROPHENYL) 5 OXO 1H 1,2,4 TRIAZOL 4(5H) YL]METHYL]BIPHENYLCARBONYLOXY]BUTOXY] 3 (PHENYLSULFONYL)[1,2,5]OXADIAZOLE 2 OXIDE; ANGIOTENSIN RECEPTOR ANTAGONIST; LOSARTAN; NITRIC OXIDE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTIHYPERTENSIVE ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG SYNTHESIS; MALE; NONHUMAN; PRIORITY JOURNAL; RABBIT; THORACIC AORTA; VASCULAR RING;

EID: 77949688617     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018010789869370     Document Type: Article

References (17)

1. Mohammad, A. Z.; Suzanne, O.; David, A. C. Drugs targeting the renin-angiotensin-aldosterone system. Nat. Rev. Drug Discov., 2002, 1, 621-636.
2. Conlin, P. R. Angiotensin II Antagonists in the Treatment of Hypertension: More Similarities than Differences. J. Clin. Hypertens., (Greenwich), 2000, 2(4), 253-257.
3. Ito, M. ACE: gene, biosynthesis and functions. Nippon Rinsho, 2005, 63(Suppl 3), 22-27.
4. Perret-Guillaume, C.; Joly, L.; Jankowski, P.; Benetos, A. Benefits of the RAS blockade: clinical evidence before the ONTARGET study. J. Hypertens., 2009, 27(Suppl 2), S3-S7.
5. Mathur, G.; Noronha, B.; Rodrigues, E.; Davis, G. The role of angiotensin II type 1 receptor blockers in the prevention and management of diabetes mellitus. Diabetes Obes. Metab., 2007, 9(5), 617-629.
6. Burnier, M.; Brunner, H. R. Angiotensin II receptor antagonists - antihypertensive agents. Expert Opin. Investig. Drugs, 1997, 6, 489-500.
7. Millatt, L. J.; Abdel-Rahman, E. M.; Siragy, H. M. Angiotensin II and nitric oxide: a question of balance. Regul. Pept., 1999, 81(1-3), 1-10.
8. Wessler, C.; Homann, A.; Fricke, U.; Lehmann, J. NO donors, part 8 [1]: synthesis and vasodilating activities of substituted benzylnitrates compared to cyclohexylmethylnitrate and GTN. Eur. J. Med. Chem., 2003, 38, 581-586.
9. Engelhardt, F. C.; Shi, Y. J.; Cowden, C. J.; Conlon, D. A.; Pipik, B.; Zhou, G.; McNamara, J. M.; Dolling, U. H. Synthesis of a NO-releasing prodrug of rofecoxib. J. Org. Chem., 2006, 71(2), 480-491.
10. Buonsanti, M. F.; Bertinaria, M.; Stilo, A. D.; Cena, C.; Fruttero, R.; Gasco, A. Nitric oxide donor beta2-agonists: furoxan derivatives containing the fenoterol moiety and related furazans. J. Med. Chem., 2007, 50(20), 5003-5011.
11. Chen, L.; Zhang, Y.; Kong, X.; Peng, S.; Tian, J. Synthesis and biological evaluation of nitric oxide-releasing derivatives of oleanolic acid as inhibitors of HepG2 cell apoptosis. Bioorg. Med. Chem. Lett., 2007, 17(11), 2979-2982.
12. Breschi, M. C.; Calderone, V.; Digiacomo, M.; Martelli, A.; Martinotti, E.; Minutolo, F.; Rapposelli, S.; Balsamo, A. NO-sartans: a new class of pharmacodynamic hybrids as cardiovascular drugs. J. Med. Chem., 2004, 47(23), 5597-5600.
13. Breschi, M. C.; Calderone, V.; Digiacomo, M.; Macchia, M.; Martelli, A.; Martinotti, E.; Minutolo, F.; Rapposelli, S.; Rossello, A.; Testai, L.; Balsamo, A. New NO-releasing pharmacodynamic hybrids of losartan and its active metabolite: design, synthesis, and biopharmacological properties. J. Med. Chem., 2006, 49(8), 2628-2639.
14. Li, Y. Q.; Ji, H.; Zhang, Y. H.; Shi, W. B.; Meng, Z. K.; Chen, X. Y.; Du, G. T. WB1106, a novel nitric oxide-releasing derivative of telmisartan, inhibits hypertension and improves glucose metabolism in rats. Eur. J. Pharmacol., 2007, 577(1-3), 100-108.
15. Xu, J.Y.; He, Q. H.; Wei, Z. Synthesis and Biological Activities of 4-Substituted-3-alky-4,5-dihydro-1-(3-chloro-4-fluorophenyl)-1,2,4-triazol-5 -one. Chin. J. Org. Chem., 2006, 26(1), 123-128.
16. Kubo, K.; Inada, Y.; Kohara, Y.; Sugiura, Y.; Ojima, M.; Itoh, K.; Furukawa, Y.; Nishikawa, K.; Naka, T. Nonpeptide angiotensin II receptor antagonists. Synthesis and biological activity of benzimidazoles. J. Med. Chem., 1993, 36(12), 1772-1784.
17. Villarroya, M.; Herrero, C. J.; Ruiz-Nuno, A.; de Pascual, R.; del Valle, M.; Michelena, P.; Grau, M.; Carrasco, E.; Lopez, M. G.; Garcia, A. G. PF9404C, a new slow NO donor with beta receptor blocking properties. Br. J. Pharmacol., 1999, 128(8), 1713-1722.