Synthesis and biological evaluation of unique stereodimers of sinomenine analogues as potential inhibitors of NO production

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 10, 2011, Pages 3096-3104

  Teng, Peng ^a   Liu, Hai Liang ^a   Deng, Zhang Shuang ^a   Shi, Zhi Bing ^a   He, Yun Mian ^a   Feng, Li Li ^a   Xu, Qiang ^a   Li, Jian Xin ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

Inhibitor; iNOS; Nitric oxide; Sinomenine; Stereodimer

Indexed keywords

17 DEMETHYL DISINOMENINE; 17 DEMETHYL SINOMENINE; 6 HYDROXYIMINO SINOMENINE; 6,7 QUINOXALINE DISINOMENINE; 6,7 QUINOXALINE SINOMENINE; 6BETA AMINO 7BETA METHOXY 7,8 DIHYDRO SINOMENINE; 7 DEMETHOXY 6 DESOXO 7, 8 DIHYDRO DISINOMENINE; 7 DEMETHOXY 6 DESOXO 7, 8 DIHYDRO SINOMENINE; NITRIC OXIDE; SINOMENINE; SINOMENINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL VIABILITY; CIRCULAR DICHROISM; CONTROLLED STUDY; CYTOKINE PRODUCTION; CYTOTOXICITY; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; MACROPHAGE; MOUSE; NONHUMAN; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; STRUCTURE ACTIVITY RELATION;

ANIMALS; ARTHRITIS, RHEUMATOID; CELL LINE; CELL SURVIVAL; DIMERIZATION; GENE EXPRESSION; MACROPHAGES; MICE; MORPHINANS; NITRIC OXIDE; NITRIC OXIDE SYNTHASE TYPE II; RNA, MESSENGER; STEREOISOMERISM;

MURINAE;

EID: 79956208522     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.04.006     Document Type: Article

References (41)

1. R. Bruckdorfer Mol. Aspects Med. 26 2005 3
2. B. Bruene Pharmacol. Res. 61 2010 265
3. Z.H. Huang, P.L. Huang, N. Panahian, T. Dalkara, M.C. Fishman, and M.A. Moskowitz Science 265 1994 1883
4. P.L. Huang, Z.H. Huang, H. Mashimo, K.D. Bloch, M.A. Moskowitz, J.A. Bevan, and M.C. Fishman Nature 377 1995 239
5. J.T. Groves, and C.C.Y. Wang Curr. Opin. Chem. Biol. 4 2000 687
6. C. Maccallini, A. Patruno, N. Besker, J.I. Ali, A. Ammazzalorso, B. De Filippis, S. Franceschelli, L. Giampietro, M. Pesce, M. Reale, M.L. Tricca, N. Re, M. Felaco, and R. Amoroso J. Med. Chem. 52 2009 1481
7. P. Vallance Fund. Clin. Pharmacol. 17 2003 1
8. J.S. Smolen, and G. Steiner Nat. Rev. Drug Disc. 2 2003 473
9. V. Strand, R. Kimberly, and J.D. Isaacs Nat. Rev. Drug Disc. 6 2007 75
10. M. Ohtsuka, F. Konno, H. Honda, T. Oikawa, M. Ishikawa, N. Iwase, K. Isomae, F. Ishii, H. Hemmi, and S. Sato J. Pharmacol. Exp. Ther. 303 2002 52
11. X.D. Hu, Y. Yang, X.G. Zhong, X.H. Zhang, Y.N. Zhang, Z.P. Zheng, Y. Zhou, W. Tang, Y.F. Yang, L.H. Hu, and J.P. Zuo J. Ethnopharmacol. 120 2008 447
12. R.J. Van't Hof, and S.H. Ralston Immunology 103 2001 255
13. M. Xu, L. Liu, C. Qi, B. Deng, and X. Cai Planta Med. 74 2008 1423
14. Y. Wang, Y.F. Fang, W.H. Huang, X. Zhou, M.H. Wang, B. Zhong, and D.Z. Peng J. Ethnopharmacol. 98 2005 37
15. B.D. Huang, A.S. He, M. Fu, P.Y. Sheng, and W.M. Liao J. Med. Plants Res. 4 2010 1830
16. Z.Q. Liu, K. Chan, H. Zhou, Z.H. Jiang, Y.F. Wong, H.X. Xu, and L. Liu Life Sci. 77 2005 3197
17. S.H. Song, X.Y. Shen, Y. Tang, Z.X. Wang, W.Y. Guo, G.S. Ding, Q.X. Wang, and Z.R. Fu Int. Immunopharmacol. 10 2010 679
18. G.D. Huang, J.B. Li, Y.H. Huang, D.F. Huang, L.J. Tang, S. Zhang, and Q. Li J. Emerg. Tradit. Chin. Med. 16 2007 416
19. H. Yamasaki Acta Med. Okayama 30 1976 1
20. K.S.H. Goto Bull. Chem. Soc. Jpn. 4 1929 107
21. K. Goto Bull. Chem. Soc. Jpn. 4 1929 129
22. Z. Zuo, X. Jimenez, L. Witte, and Z.P. Zhu Protein Eng. 13 2000 361
23. J.F. Amara, T. Clackson, V.M. Rivera, T. Guo, T. Keenan, S. Natesan, R. Pollock, W. Yang, N.L. Courage, D.A. Holt, and M.P. Gilman Natl. Acad. Sci. U.S.A. 94 1997 10618
24. Z.S. Deng, J.X. Li, P. Teng, P. Li, and X.R. Sun Org. Lett. 10 2008 1119
25. Z.S. Deng, Y. Zhao, C.C. He, J. Jin, Y.M. He, and J.X. Li Org. Lett. 10 2008 3879
26. J.I. Minamikawa, I. Tijima, and A. Brossi Heterocycles 10 1978 79
27. K.I.R. Goto Chem. Pharm. Bull. 1931 93
28. Christians, U. K., V. W. U.S. Patent, 6372756B1, 2002.
29. W.M. Cheng, F. Qiu, and X.S. Yao J. Asian Nat. Prod. Res. 9 2007 13
30. K. McCamley, J.A. Ripper, R.D. Singer, and P.J. Scammells J. Org. Chem. 68 2003 9847
31. I. Iijima, J.I. Minamikawa, A.E. Jacobson, A. Brossi, and K.C. Rice J. Org. Chem. 43 1978 1462
32. L.M. Sayre, and P.S. Portoghese J. Org. Chem. 45 1980 3366
33. D.D. Weller, and H. Rapoport J. Med. Chem. 19 1976 1171
34. M.D. Bachi, E.E. Korshin, R. Hoos, A.M. Szpilman, P. Ploypradith, S.J. Xie, T.A. Shapiro, and G.H. Posner J. Med. Chem. 46 2003 2516
35. P.S. Portoghese, H. Nagase, K.E. Maloneyhuss, C.E. Lin, and A.E. Takemori J. Med. Chem. 34 1991 1715
36. J.F. Li, Y. Zhao, M.M. Cai, X.F. Li, and J.X. Li Eur. J. Med. Chem. 44 2009 2796
37. K.S.H. Goto Bull. Chem. Soc. Jpn. 10 1935 597
38. Y.T. Lou, H.B. Zhou, J. Zou, L.C. Yan, E.G. Bi, B. Sun, and Z.J. Yao Tetrahedron Lett. 51 2010 485
39. Q.W. Xie, R. Whisnant, and C. Nathan J. Exp. Med. 177 1993 1779
40. M. Ciz, M. Pavelkova, L. Gallova, J. Kralova, L. Kubala, and A. Lojek Physiol. Res. 57 2008 393
41. K.S. Kang, N. Yamabe, H.Y. Kim, T. Okamoto, Y. Sei, and T. Yokozawa J. Ethnopharmacol. 113 2007 225