Novel nitric oxide-releasing isochroman-4-one derivatives: Synthesis and evaluation of antihypertensive activity

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 23, 2012, Pages 6848-6855

  Bai, Renren ^a   Yang, Xue ^a   Zhu, Yao ^a   Zhou, Zhiwen ^a   Xie, Weijia ^a   Yao, Hequan ^a   Jiang, Jieyun ^b   Liu, Jie ^a   Shen, Mingqin ^c   Wu, Xiaoming ^a   Xu, Jinyi ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b UNIVERSITY OF KENTUCKY   (United States)

^c Jiangsu Provincial Institute of Traditional Chinese Medicine   (China)

Author keywords

Antihypertensive activity; Hybrids; Isochroman 4 one derivatives; Nitric oxide (NO); Structure modification

Indexed keywords

2 (6 METHOXY 3 METHYL 4 OXOISOCHROMAN 7 YLOXY)ETHYLNITRATE; 2 (7 METHOXY 3 METHYL 4 OXOISOCHROMAN 6 YLOXY)ETHYLNITRATE; 2 (7 METHOXY 3 METHYL 4 OXOISOCHROMAN 8 YLOXY)ACETIC ACID; 2 (7 METHOXY 3 METHYL 4 OXOISOCHROMAN 8 YLOXY)ETHYLNITRATE; 2 (NITROOXY)ETHYL 2 (6 METHOXY 3 METHYL 4 OXOISOCHROMAN 7 YLOXY)ACETATE; 2 (NITROOXY)ETHYL 2 (7 METHOXY 3 METHYL 4 OXOISOCHROMAN 6 YLOXY)ACETATE; 2 (NITROOXY)ETHYL 2 (7 METHOXY 3 METHYL 4 OXOISOCHROMAN 8 YLOXY)ACETATE; 3 (6 METHOXY 3 METHYL 4 OXOISOCHROMAN 7 YLOXY)PROPYLNITRATE; 3 (7 METHOXY 3 METHYL 4 OXOISOCHROMAN 6 YLOXY)PROPYLNITRATE; 3 (7 METHOXY 3 METHYL 4 OXOISOCHROMAN 8 YLOXY)PROPYLNITRATE; 3 (NITROOXY)PROPYL 2 (6 METHOXY 3 METHYL 4 OXOISOCHROMAN 7 YLOXY)ACETATE; 3 (NITROOXY)PROPYL 2 (7 METHOXY 3 METHYL 4 OXOISOCHROMAN 6 YLOXY)ACETATE; 3 (NITROOXY)PROPYL 2 (7 METHOXY 3 METHYL 4 OXOISOCHROMAN 8 YLOXY)ACETATE; 4 (6 METHOXY 3 METHYL 4 OXOISOCHROMAN 7 YLOXY)BUTYLNITRATE; 4 (7 METHOXY 3 METHYL 4 OXOISOCHROMAN 6 YLOXY)BUTYLNITRATE; 4 (7 METHOXY 3 METHYL 4 OXOISOCHROMAN 8 YLOXY)BUTYLNITRATE; 4 (NITROOXY)BUTYL 2 (6 METHOXY 3 METHYL 4 OXOISOCHROMAN 7 YLOXY)ACETATE; 4 (NITROOXY)BUTYL 2 (7 METHOXY 3 METHYL 4 OXOISOCHROMAN 6 YLOXY)ACETATE; 4 (NITROOXY)BUTYL 2 (7 METHOXY 3 METHYL 4 OXOISOCHROMAN 8 YLOXY)ACETATE; 8 (2 BROMOETHOXY) 7 METHOXY 3 METHYLISOCHROMAN 4 ONE; 8 (3 BROMOPROPOXY) 7 METHOXY 3 METHYLISOCHROMAN 4 ONE; 8 (4 BROMOBUTOXY) 7 METHOXY 3 METHYLISOCHROMAN 4 ONE; CAPTOPRIL; ISOCHROMAN DERIVATIVE; NITRIC OXIDE DONOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIHYPERTENSIVE ACTIVITY; ARTICLE; BLOOD PRESSURE REGULATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HYPERTENSION; IN VITRO STUDY; IN VIVO STUDY; MALE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIHYPERTENSIVE AGENTS; BLOOD PRESSURE; CHROMONES; HUMANS; HYPERTENSION; MALE; NITRIC OXIDE; NITRIC OXIDE DONORS; RATS; RATS, INBRED SHR;

EID: 84869096407     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.09.043     Document Type: Article

References (26)

1. S. Moncada, and A.N. Higgs Engl. J. Med. 1993 2002 329
2. Y. Higashi, S. Sasaki, K. Nakagawa, M. Kimura, K. Noma, S. Sasaki, K. Hara, H. Matsuura, C. Goto, T. Oshima, and K. Chayama J. Am. Coll. Cardiol. 42 2003 256
3. H. Hu, S. Zharikov, and J.M. Patel Peptides 35 2012 78
4. M.-H. Tai, L.-L. Wang, K.L.H. Wu, and J.Y.H. Chan Free Radic. Biol. Med. 38 2005 450
5. S. Fiorucci, E. Antonelli, and A. Morelli Dig. Liver Dis. 35 2003 S61
6. M.A. Lovich, N.K. Bruno, C.P. Plant, A.E. Wei, G.B. Vasquez, B.J. Johnson, D.H. Fine, and R.J. Gilbert Nitric Oxide 24 2011 204
7. S.V. Bhandari, K.G. Bothara, A.A. Patil, T.S. Chitre, A.P. Sarkate, S.T. Gore, S.C. Dangre, and C.V. Khachane Bioorg. Med. Chem. 17 2009 390
8. Y.-Q. Li, H. Ji, Y.-H. Zhang, W.-B. Shi, Z.-K. Meng, X.-Y. Chen, G.-T. Du, and J.-D. Tian Eur. J. Pharmacol. 577 2007 100
9. M.C. Breschi, V. Calderone, M. Digiacomo, A. Martelli, E. Martinotti, F. Minutolo, S. Rapposelli, and A. Balsamo J. Med. Chem. 47 2004 5597
10. M. Jayachandran, T. Hayashi, D. Sumi, N.K. Thakur, H. Kano, L.J. Ignarro, and A. Iguchi Biochem. Bioph. Res. Commun. 280 2001 589
11. M. Villarroya, M.G. López, R. de Pascual, and A.G. García Cardiovasc. Drug Rev. 23 2005 149
12. S. Visentin, B. Rolando, A. Di Stilo, R. Fruttero, M. Novara, E. Carbone, C. Roussel, N. Vanthuyne, and A. Gasco J. Med. Chem. 47 2004 2688
13. Y. Iwanaga, Y. Gu, T. Dieterle, C. Presotto, P. Soldato, K.L. Peterson, E. Ongini, G. Condorelli, and J. Ross FASEB. J. 18 2004 587
14. Y.C. Li Curr. Opin. Invest. Drugs 8 2007 750
15. H. Qian, W.L. Huang, X.M. Wu, H.B. Zhang, J.P. Zhou, and W.C. Ye Chin. Chem. Lett. 18 2007 1227
16. J. Liu, H. Ren, J.Y. Xu, R.R. Bai, Q. Yan, W.L. Huang, X.M. Wu, J.H. Fu, Q.J. Wang, Q. Wu, and R. Fu Bioorg. Med. Chem. Lett. 2009 1822 19
17. R.R. Bai, J. Liu, Y. Zhu, X. Yang, C. Yang, L.Y. Kong, X.B. Wang, H.Y. Zhang, H.Q. Yao, M.Q. Shen, X.M. Wu, and J.Y. Xu Bioorg. Med. Chem. Lett. 22 2012 6490
18. D.H. Li, L. Wang, H. Cai, Y.H. Zhang, and J.Y. Xu Molecules 17 2012 7557
19. Y. Li, X.L. Wang, R. Fu, W.Y. Yu, X.L. Wang, Y.S. Lai, S.X. Peng, and Y.H. Zhang Bioorg. Med. Chem. Lett. 21 2011 4210
20. X.-Q. Zou, S.-M. Peng, C.-P. Hua, L.-F. Tan, Q. Yuan, H.-W. Deng, and Y.-J. Li Bioorg. Med. Chem. 18 2010 3020
21. W.K. Liu, C.Z. Liu, C.G. Gong, W.Y. Lin, and C.C. Guo Bioorg. Med. Chem. Lett. 19 2009 1647
22. X. Tang, X. Gu, H. Ai, G. Wang, H. Peng, Y. Lai, and Y. Zhang Bioorg. Med. Chem. Lett. 22 2012 801
23. Y. Ling, X. Ye, Z. Zhang, Y. Zhang, Y. Lai, H. Ji, S. Peng, and J. Tian J. Med. Chem. 54 2011 3251
24. W.-H. Huang, J. Sun, H. He, H.-W. Dong, and J.-T. Li Food Chem. 128 2011 968
25. N.-C. Yang, K.-Y. Jhou, and C.-Y. Tseng Food Chem. 132 2012 1796
26. C.F. Ng, C.M. Koon, D.W.S. Cheung, M.Y. Lam, P.C. Leung, C.B.S. Lau, and K.P. Fung J. Ethnopharmacol. 137 2011 1366