Abstract
Inhibitory effect on tumor necrosis factor-α (TNF-α) production by sinomenine derivatives with embedment of small drug-like nitrogen hetereocyclic moieties has been studied in this work. Several new sinomenine derivatives having chlorophenyl substituent have been found to exhibit much more potent TNF-α inhibitory activity than natural sinomenine and other derivatives.
Similar content being viewed by others
References
Wermuth CG. The Practice of Medicinal Chemistry, 2nd ed. San Diego: Academic Press. 2003
Keller TH, Pichota A, Yin Z. A practical view of ‘ruggability’. Curr Opin Chem Biol, 2006, 10: 357–361
Knorr L, Horlein H. Über ein neues chlorokodid. XVI. Mitteilung: Zur kenntnis des morphins von Ludwig Knorr. Chem Ber, 1907, 40: 4883–4889
Wang Y, Fang Y, Huang W, Zhou X, Wang M, Zhong B, Peng D. Effect of sinomenine on cytokine expression of macrophages and synoviocytes in adjuvant arthritis rats. J Ethnopharmacol, 2005, 98: 37–43
Zhao Y, Li J, Yu KQ, Liu Y, Chen XG. Sinomenine inhibits maturation of monocyte-derived dendritic cells through blocking activation of NF-kappa B. Int J Immunopharmacol, 2007, 7: 637–645
Ou, YQ, Chen LH, Li, XJ, Lin ZB, Li WD. Sinomenine influences capacity for invasion and migration in activated human monocytic THP-1 cells by inhibiting the expression of MMP-2, MMP-9, and CD147. Acta Pharm Sinica, 2009, 30: 435–441
Previous modifications on sinomenine, see: Wu F, Feng X, Wu K, Cheng G, Huang Y, Ye X, Qiu P, Zheng X. Sinomenine structure-modified compound and its preparation method. CN1876634-A, 2007
Luo J, Zeng H, Li Y, Yin S. 1-Substituted amine methyl diversine derivative and its preparation method. CN1948291-A, 2007
Whittall J, Mather P. New 1,7-dibromodihydrocodeinone dimethylketal and its derivatives useful in the manufacture of a medicament for the treatment or prophylaxis of pain. WO2004022564-A3 (AU2003263301-A8), 2004
Qin G, Tang X, Wang R, Zhou T, Lestage P, Caignard D, Renard P. New sinomenine derivatives useful for treatment of deficiencies of memory associated with cerebral aging and with neurodegenerative diseases. WO2004048340-A1 (CN1504469-A), 2004
Yakida A, Sukegawa Y. Intestinal disorder preventative and treating agent-comprises Stephania plant-derived alkaloid, useful for treating e.g. enteritis, Crohn’s disease etc. JP8301778-A, 1997
Ibuka T, Kitano M. Studies on the alkaloids of Menispermaceous plants. CCXXXIX. Synthesis of hasubanan derivative from sinomenine. Chem Pharm Bull, 1967, 15: 1944–1947
Shionogi & Co. Ltd. Purification of morphinan derivatives. JP64021845-B, 1966
Shionogi & Co. Ltd., 6-Methylenemorphinan derivatives. JP65010153-B, 1966
Shionogi & Co. Ltd., 6,7-Dihydroxymorphinan derivatives. JP65010217-B, 1966
Wu F, Zheng X, Qiu P, Qiu S. Sinomenine salt compound and its preparation method. CN1995019-A, 2008
Pan Y, Li Y, Bu Q, Huang L, Wang J, Li J. 17-Sulfonyl sinomenine, has potential medicinal application prospect providing structure formula, preparation method and concrete steps. CN1785977-A, 2006
Pan Y, Li Y, Bu Q, Huang L, Wang J, Li J. N-Alkyl sinomenine has potential medicinal application prospect. CN1785976-A, 2006
Christians U, Kaever VW. New compound N-demethyl-sinomenine. WO9942105-A (US6372756-B1), 1999
Tang Q, Luo J, Zhu Q, Li Y, Yin S. Synthesis and anti-inflammatory activities investigation of sinomenine derivatives on ring C. Nat Prod Res, 2006, 20: 1015–1023
Yao ZJ, Zhou HB. Derivative of sinomenine with pyrazine cycle being connected to C cycle, its synthetic method and application. CN1687065-A (ZL 200510024478.9), 2006
Yao ZJ, Zhou HB. Sinomenine derivative with C cycle connected to five-membered heterocycle and its preparation. CN1687070-A (ZL 200510024479. 3), 2006
Lou YT, Zhou HB, Zou J, Yan LC, Bi EG, Sun B, Yao ZJ. Modification of poorly bioactive sinomenine into more potent immunosuppressive agents by embedding of drug-like fragments. Tetrahedron Lett, 2010, 51: 485–488
Yan LC, Bi EG, Lou YT, Wu XD, Liu ZD, Zou J, Wang Y, Ma Z, Lin GM, Sun SH, Bian C, Chen AZ, Yao ZJ, Sun B. Novel sinomenine derivative 1032 improves immune suppression in experimental autoimmune encephalomyelitis. Biochem. Biophys Res Comm, 2010, 391: 1093–1098
Smolen JS, Steiner G. Therapeutic strategies for rheumatoid arthritis. Nat Rev Drug Discov, 2003, 2, 473–488
Ye XR, Yan KX, Wu KM, Feng XZ, Huang YM, Qiu P. Synthesis and anti-inflammatory analgesic activities of sinomenine derivatives. Acta Pharm Sinica, 2004, 39, 180–183
Iijima I, Minamikawa J, Jacobson AE, Rice KC. Studies in the (+)-morphinan series. 4. A markedly improved synthesis of (+)-morphine. J Org Chem, 1978, 43: 1462–1463
Qin GW, Tang XC, Wang R, Zhou TX, Lestage P, Caignard DH, Renard P. New sinomenine derivatives useful for treatment of deficiencies of memory associated with cerebral aging and with neurodegenerative diseases. WO2004048340, 2004
Fleischhacker W, Viebock F, Zeidler F. Strukturund konfigurationsbeweis für das diketon aus 14-bromcodeinon. Monatsh. Chem, 1970, 101: 1215–1222
Breedveld FC. Antagonisten van tumornecrosisfactor: Infliximab, adalimumab en etanercept. Ned Tijdschr Geneeskd, 2005, 149: 2273–2277
Manthey CL, Wang SW, Kinney SD, Yao Z. SB202190, a selective inhibitor of p38 mitogen-activated protein kinase, is a powerful regulator of LPS-induced mRNAs in monocytes. J Leukocyte Biol, 1998, 64: 409–417
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Wang, M., Ma, L., Lou, Y. et al. Sinomenine derivatives with embedment of nitrogen-containing heterocycles exhibiting potent TNF-αinhibitory activity. Sci. China Chem. 55, 2537–2547 (2012). https://doi.org/10.1007/s11426-012-4588-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-012-4588-8