Discovery and structure-activity relationships of phenyl benzenesulfonylhydrazides as novel indoleamine 2,3-dioxygenase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 15, 2014, Pages 3403-3406

  Cheng, Ming Fu ^a   Hung, Ming Shiu ^a   Song, Jen Shin ^a   Lin, Shu Yu ^a   Liao, Fang Yu ^a   Wu, Mine Hsine ^a   Hsiao, Wenchi ^a   Hsieh, Chia Ling ^a   Wu, Jian Sung ^a   Chao, Yu Sheng ^a   Shih, Chuan ^a   Wu, Su Ying ^a   Ueng, Shau Hua ^a  

^a NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

Author keywords

Indoleamine 2,3 dioxygenase; Molecular docking; Structure activity relationship; Sulfonylhydrazide

Indexed keywords

ANTINEOPLASTIC AGENT; HYDRAZIDE DERIVATIVE; INDOLEAMINE 2,3 DIOXYGENASE INHIBITOR; IRON; PHENYL BENZENESULFONYLHYDRAZIDE; SULFONE; UNCLASSIFIED DRUG; 4-((2-(4-BROMOPHENYL)HYDRAZINYL)SULFONYL)BENZOIC ACID; ENZYME INHIBITOR; INDOLEAMINE 2,3 DIOXYGENASE; PHENYLHYDRAZINE DERIVATIVE; SULFONAMIDE; BENZENE DERIVATIVE; HALOGEN; HYDROGEN; PHENYL GROUP;

ARTICLE; CROSS COUPLING REACTION; DRUG POTENCY; DRUG SYNTHESIS; ENZYMATIC ASSAY; HELA CELL LINE; HUMAN; HUMAN CELL; HYDROGEN BOND; HYDROPHOBICITY; IC 50; STRUCTURE ACTIVITY RELATION; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG DEVELOPMENT; HIGH THROUGHPUT SCREENING; METABOLISM; SYNTHESIS; ANTINEOPLASTIC ACTIVITY; CONTROLLED STUDY; DRUG BINDING SITE; DRUG CONFORMATION; EC50; ENZYME ACTIVITY; FEMALE; IC50;

DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DISCOVERY; ENZYME INHIBITORS; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; INDOLEAMINE-PYRROLE 2,3,-DIOXYGENASE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHENYLHYDRAZINES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84904059888     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2014.05.084     Document Type: Article

References (33)

1. WHO website release: http://globocan.iarc.fr/Pages/fact-sheets-cancer. aspx.
2. I. Mellman, G. Coukos, and G. Dranoff Nature 480 2011 480
3. D.M. Pardoll Nat. Rev. Cancer 12 2012 252
4. M.E. Keir, M.J. Butte, G.J. Freeman, and A.H. Sharpe Annu. Rev. Immunol. 26 2008 677
5. J. Weber Semin. Oncol. 37 2010 430
6. S.L. Topalian et al. N. Eng. J. Med. 366 2012 2443
7. C. Uyttenhove, L. Pilotte, I. Théate, V. Stroobant, D. Colau, N. Parmentier, T. Boon, and B. Van den Eynde J. Nat. Med. 9 2003 1269
8. D.H. Munn Curr. Med. Chem. 18 2011 2240
9. S. Löb, A. Königsrainer, H.-G. Rammensee, G. Opelz, and P. Terness Nat. Rev. Cancer 9 2009 445
10. D.-Y. Hou, A.J. Muller, M.D. Sharma, J. DuHadaway, T. Banerjee, M. Johnson, A.L. Mellor, G.C. Prendergast, and D.H. Munn Cancer Res. 67 2007 792
11. H.K. Koblish, M.J. Hansbury, K.J. Bowman, G. Yang, C.L. Neilan, P.J. Haley, T.C. Burn, P. Waeltz, R.B. Sparks, E.W. Yue, A.P. Combs, P.A. Scherle, K. Vaddi, and J.S. Fridman Mol. Cancer Ther. 9 2010 489
12. P. Gaspari, T. Banerjee, W.P. Malachowski, A.J. Muller, G.C. Prendergast, J.B. DuHadaway, S. Bennett, and A.M. Donovan J. Med. Chem. 49 2006 684
13. A.J. Muller, J.B. DuHadaway, P.S. Donover, E. Sutanto-Ward, and G.C. Prendergast Nat. Med. 11 2005 312
14. S. Kumar, W.P. Malachowski, J.B. DuHadaway, J.M. LaLonde, P.J. Carroll, D. Jaller, R. Metz, G.C. Prendergast, and A.J. Muller J. Med. Chem. 51 2008 1706
15. G. Carr, M.K.W. Chung, A.G. Mauk, and R.J. Andersen J. Med. Chem. 51 2008 2634
16. S. Yang, X. Li, F. Hu, Y. Li, Y. Yang, J. Yan, C. Kuang, and Q. Yang J. Med. Chem. 56 2013 8321
17. C. Carvalho, D. Siegel, M. Inman, R. Xiong, D. Ross, and C.J. Moody Org. Biomol. Chem. 12 2014 2663
18. S. Kumar, D. Jaller, B. Patel, J.M. LaLonde, J.B. DuHadaway, W.P. Malachowski, G.C. Prendergast, and A.J. Muller J. Med. Chem. 51 2008 4968
19. Q. Huang, M. Zheng, S. Yang, C. Kuang, C. Yu, and Q. Yang Eur. J. Med. Chem. 46 2011 5680
20. U.F. Röhrig, S.R. Majjigapu, A. Grosdidier, S. Bron, V. Stroobant, L. Pilotte, D. Colau, P. Vogel, B.J. Van den Eynde, V. Zoete, and O. Michielin J. Med. Chem. 55 2012 5270
21. E. Dolušić, P. Larrieu, S. Blanc, F. Sapunaric, B. Norberg, L. Moineaux, D. Colette, V. Stroobant, L. Pilotte, D. Colau, T. Ferain, G. Frasr, M. Galeni, J.-M. Frère, B. Masereel, B. Van den Eynde, J. Wouters, and R. Frédérick Bioorg. Med. Chem. 19 2011 1550
22. Roehrig, U.; Loay, A.; Michielin, O.; Benoit Van, D. E.; Pilotte, L.; Stroobant, V.; Larrieu, P. WO patent, WO2009127669 A3, 2010.
23. K. Matsuno, H. Yamazaki, Y. Isaka, K. Takai, Y. Unno, N. Ogo, Y. Ishikawa, S. Fujii, O. Takikawa, and A. Asai Med. Chem. Commun. 3 2012 475
24. E.W. Yue, B. Douty, B. Wayland, M. Bower, X. Liu, L. Leffet, Q. Wang, K.J. Bowman, M.J. Hansbury, C. Liu, M. Wei, Y. Li, R. Wynn, T.C. Burn, H.K. Koblish, J.S. Fridman, B. Metcalf, P.A. Scherle, and A.P. Combs J. Med. Chem. 52 2009 7364
25. K. Matsuno, K. Takai, Y. Isaka, Y. Unno, M. Sato, O. Takikawa, and A. Asai Bioorg. Med. Chem. Lett. 20 2010 5126
26. Incyte website press release http://investor.incyte.com/phoenix.zhtml?c= 69764&p=irol-newsArticle&ID=1826050&highlight=.
27. R. Larock Comprehensive Organic Transformations 1989 VCH Publishers
28. T.W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis 3rd ed. 1999 John Wiley and Sons
29. L. Fieser, and M. Fieser Fieser and Fieser's Reagents for Organic Synthesis 1994 John Wiley and Sons
30. L. Paquette Encyclopedia of Reagents for Organic Synthesis 1995 John Wiley and Sons
31. N. Zhao, Y. Li, Y. Wang, and J. Wang J. Sulfur Chem. 27 2006 427
32. J. Leban, S. Pegoraro, M. Dormeyer, M. Lanzer, A. Aschenbrenner, and B. Kramer Bioorg. Med. Chem. Lett. 14 2004 1979
33. Lin, P.; Chang, L.; Edmondson, S. WO patent, WO2010129326 A1, 2010.