Synthesis and biological evaluation of cyanoguanidine derivatives of loratadine

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 19, 2012, Pages 6076-6080

  Liu, Wukun ^a,b   Zhou, Jinpei ^a   Zhang, Tong ^a   Zhang, Huibin ^a   Zhu, Haiyang ^a   Cheng, Yanhua ^a   Gust, Ronald ^b,c  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

^c UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

Anti inflammation; Antitumor; Benzo 5,6 cyclohepta 1,2 b pyridine; Cyanoguanidine derivatives; Loratadine

Indexed keywords

4 [(8 CHLORO 5,6 DIHYDRO 11H BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN 11 YLIDENE)] N CYANO N' 1 PHENYLETHYL 1 PIPERIDINECARBOXIMIDAMIDE; 4 [(8 CHLORO 5,6 DIHYDRO 11H BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN 11 YLIDENE)] N CYANO N' 1 PIPERIDINECARBOXIMIDAMIDE; 4 [(8 CHLORO 5,6 DIHYDRO 11H BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN 11 YLIDENE)] N CYANO N' 1 PIPERIDINECARBOXIMIDOTHIOIC ACID METHYL ESTER; 4 [(8 CHLORO 5,6 DIHYDRO 11H BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN 11 YLIDENE)] N CYANO N' 2 PHENYLETHYL 1 PIPERIDINECARBOXIMIDAMIDE; 4 [(8 CHLORO 5,6 DIHYDRO 11H BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN 11 YLIDENE)] N CYANO N' [2 (3,4 DIMETHOXYPHENYL)ETHYL] 1 PIPERIDINECARBOXIMIDAMIDE; 4 [(8 CHLORO 5,6 DIHYDRO 11H BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN 11 YLIDENE)] N CYANO N' [2 (3,4 METHYLENEDIOXYPHENYL)ETHYL] 1 PIPERIDINECARBOXIMIDAMIDE; 4 [(8 CHLORO 5,6 DIHYDRO 11H BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN 11 YLIDENE)] N CYANO N' BENZYL 1 PIPERIDINECARBOXIMIDAMIDE; 4 [(8 CHLORO 5,6 DIHYDRO 11H BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN 11 YLIDENE)] N CYANO N' BUTYL 1 PIPERIDINECARBOXIMIDAMIDE; 4 [(8 CHLORO 5,6 DIHYDRO 11H BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN 11 YLIDENE)] N CYANO N' CYCLOHEXYL 1 PIPERIDINECARBOXIMIDAMIDE; 4 [(8 CHLORO 5,6 DIHYDRO 11H BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN 11 YLIDENE)] N CYANO N' OCTYL 1 PIPERIDINECARBOXIMIDAMIDE; DESLORATADINE; DICYANODIAMIDE DERIVATIVE; FLUOROURACIL; GUANIDINE DERIVATIVE; IBUPROFEN; LONAFARNIB; LORATADINE; RUPATADINE; UNCLASSIFIED DRUG; XYLENE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL STRAIN MCF 7; COLON CARCINOMA; CONTROLLED STUDY; CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; IN VIVO STUDY; MOUSE; NONHUMAN; SWELLING;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; EAR DISEASES; GUANIDINES; HT29 CELLS; HUMANS; LORATADINE; MALE; MCF-7 CELLS; MICE; MICE, INBRED STRAINS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; XYLENES;

MUS;

EID: 84866370397     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.08.041     Document Type: Article

References (25)

1. R.A. Smith, V. Cokkinides, D. Brooks, D. Saslow, M. Shah, and O.W. Brawley CA Cancer J. Clin. 61 2011 8
2. E.W. Gelfand, S. Appajosyula, and S. Meeves Curr. Med. Res. Opin. 20 2004 73
3. D.K. Agrawal Clin. Exp. Allergy 34 2004 1342
4. Y. Wang, J. Wang, Y. Lin, L.F. Si-Ma, D.H. Wang, L.G. Chen, and D.K. Liu Bioorg. Med. Chem. Lett. 21 2011 4454
5. G.Z. Liu, H.W. Xu, G.W. Chen, P. Wang, Y.N. Wang, H.M. Liu, and D.Q. Yu Bioorg. Med. Chem. 18 2010 1626
6. B.P. Soule, N.L. Simone, W.G. DeGraff, R. Choudhuri, J.A. Cook, and J.B. Mitchell Radiat. Oncol. 5 2010 8
7. J.S. Chen, S.Y. Lin, W.L. Tso, G.C. Yeh, W.S. Lee, H. Tseng, L.C. Chen, and Y.S. Ho Mol. Carcinog. 45 2006 461
8. T. Robak, A. Szmigielska-Kaplon, A. Pluta, O. Grzybowska-Izydorczyk, A. Wolska, M. Czemerska, and A. Wierzbowska Curr. Med. Chem. 18 2011 638
9. C. Castaneda, K.L. Meadows, R. Truax, M.A. Morse, S.H. Kaufmann, W.P. Petros, Y. Zhu, P. Statkevich, D.L. Cutler, and H.I. Hurwitz Cancer Chemother. Pharmacol. 67 2011 455
10. H.Y. Zhu, A.B. Cooper, J. Desai, G. Njoroge, P. Kirschmeier, W.R. Bishop, C. Strickland, A. Hruza, R.J. Doll, and V.M. Girijavallabhan Bioorg. Med. Chem. Lett. 20 2010 1134
11. A.D. Basso, A. Mirza, G. Liu, B.J. Long, W.R. Bishop, and P. Kirschmeier J. Biol. Chem. 280 2005 31101
12. W. Liu, J. Zhou, T. Zhang, H. Zhu, H. Qian, H. Zhang, W. Huang, and R. Gust Bioorg. Med. Chem. Lett. 22 2012 2701
13. B.C. Sasse, U.R. Mach, J. Leppaenen, T. Calmels, and H. Stark Bioorg. Med. Chem. 15 2007 7258
14. J.J. Piwinski, J.K. Wong, M.J. Green, A.K. Ganguly, M.M. Billah, R.E. West Jr., and W. Kreutner J. Med. Chem. 34 1991 457
15. R. Geyer, and A. Buschauer Arch. Pharm. 344 2011 775
16. P. Igel, S. Dove, and A. Buschauer Bioorg. Med. Chem. Lett. 20 2010 7191
17. T. Birnkammer, A. Spickenreither, I. Brunskole, M. Lopuch, N. Kagermeier, G. Bernhardt, S. Dove, R. Seifert, S. Elz, and A. Buschauer J. Med. Chem. 55 2012 1147
18. E. Binderup, F. Bjorkling, P.V. Hjarnaa, S. Latini, B. Baltzer, M. Carlsen, and L. Binderup Bioorg. Med. Chem. Lett. 15 2005 2491
19. S.L. Li, C.H. Huang, C.C. Lin, Z.N. Huang, J.H. Chern, H.Y. Lien, Y.Y. Wu, C.H. Cheng, C.Y. Chang, and J.J. Chuu Invest. New Drugs 29 2011 195
20. R. Wolin, M. Connolly, J. Kelly, J. Weinstein, S. Rosenblum, A. Afonso, L. James, P. Kirschmeier, and W.R. Bishop Bioorg. Med. Chem. Lett. 8 1998 2521
21. A.B. Cooper, C.L. Strickland, J. Wang, J. Desai, P. Kirschmeier, R. Patton, W.R. Bishop, P.C. Weber, and V. Girijavallabhan Bioorg. Med. Chem. Lett. 12 2002 601
22. X. Florence, S. Sebille, P. Tullio, P. Lebrun, and B. Pirotte Bioorg. Med. Chem. 17 2009 7723
23. Y. Shi, J. Zhang, M. Shi, S.P. O'Connor, S.N. Bisaha, C. Li, D. Sitkoff, A.T. Pudzianowski, S. Chong, H.E. Klei, K. Kish, J. Yanchunas Jr., E.C. Liu, K.S. Hartl, S.M. Seiler, T.E. Steinbacher, W.A. Schumacher, K.S. Atwal, and P.D. Stein Bioorg. Med. Chem. Lett. 19 2009 4034
24. W. Liu, J. Zhou, K. Bensdorf, H. Zhang, H. Liu, Y. Wang, H. Qian, Y. Zhang, A. Wellner, G. Rubner, W. Huang, C. Guo, and R. Gust Eur. J. Med. Chem. 46 2011 907
25. W. Liu, J. Zhou, Y. Liu, H. Liu, K. Bensdorf, C. Guo, and R. Gust Arch. Pharm. 344 2011 487