메뉴 건너뛰기




Volumn 59, Issue 1, 2016, Pages 419-430

Phenyl Benzenesulfonylhydrazides Exhibit Selective Indoleamine 2,3-Dioxygenase Inhibition with Potent in Vivo Pharmacodynamic Activity and Antitumor Efficacy

Author keywords

[No Author keywords available]

Indexed keywords

1 ACETYL 2,3 DIHYDRO 1H INDOLE 5 SULFONYL CHLORIDE; 1 ACETYL N' (4 BROMOPHENYL) 2,3 DIHYDRO 1H INDOLE 5 SULFONYL HYDRAZIDE; 2 AMINO N' (4 BROMOPHENYL) 1H BENZIMIDAZOLE 5 SULFONYL HYDRAZIDE; 2 OXO 1,2 DIHYDRO 6 QUINOLINESULFONYL CHLORIDE; 2 OXO 1,2,3,4 TETRAHYDROQUINOLINE 6 SULFONYL CHLORIDE; 2 OXO 2,3 DIHYDRO 1H BENZIMIDAZOLE 5 SULFONYL CHLORIDE; 2 OXO 2,3 DIHYDRO 1H INDOLE 5 SULFONYL CHLORIDE; 2 OXO 2,3,4,5 TETRAHYDRO 1H 1 BENZAZEPINE 7 SULFONYL CHLORIDE; 2,3 DIOXO 2,3 DIHYDRO 1H INDOLE 5 SULFONYL CHLORIDE; 3,3 DIFLUORO 2 OXO 2,3 DIHYDRO 1H NDOLE 5 SULFONYL CHLORIDE; 3,3 DIMETHYL 2 OXO 2,3 DIHYDRO 1H INDOLE 5 SULFONYL CHLORIDE; 4 (2 OXOPYRROLIDIN 1 YL)BENZENESULFONYL CHLORIDE; ANTINEOPLASTIC AGENT; BENZENE DERIVATIVE; CYCLOPHOSPHAMIDE; HYDRAZIDE DERIVATIVE; INDOLEAMINE 2,3 DIOXYGENASE INHIBITOR; KYNURENINE; N' (4 BROMOPHENYL) 1 METHYL 2 OXO 2,3 DIHYDRO 1H INDOLE 5 SULFONYL HYDRAZIDE; N' (4 BROMOPHENYL) 1,3 DIMETHYL 2 OXO 2,3 DIHYDRO 1H BENZIMIDAZOLE 5 SULFONYL HYDRAZIDE; N' (4 BROMOPHENYL) 2 OXO 1,2,3,4 TETRAHYDROQUINOLINE 6 SULFONYL HYDRAZIDE; N' (4 BROMOPHENYL) 2 OXO 2,3 DIHYDRO 1H BENZIMIDAZOLE 5 SULFONYL HYDRAZIDE; N' (4 BROMOPHENYL) 2 OXO 2,3 DIHYDRO 1H INDOLE 5 SULFONYL HYDRAZIDE; N' (4 BROMOPHENYL) 2,3 DIOXO 2,3 DIHYDRO 1H INDOLE 5 SULFONOHYDRAZIDE; N' (4 BROMOPHENYL) 3,3 DIFLUORO 2 OXO 2,3 DIHYDRO 1H INDOLE 5 SULFONYL HYDRAZIDE; N' (4 BROMOPHENYL) 3,3 DIMETHYL 2 OXO 2,3 DIHYDRO 1H INDOLE 5 SULFONYL HYDRAZIDE; N' (4 BROMOPHENYL) 4 (2 OXOPYRROLIDIN 1 YL)BENZENESULFONYL HYDRAZIDE; PHENYL BENZENESULFONYL HYDRAZIDE; TRYPTOPHAN; UNCLASSIFIED DRUG; UNINDEXED DRUG; ENZYME INHIBITOR; INDOLEAMINE 2,3 DIOXYGENASE;

EID: 84955140232     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b01640     Document Type: Article
Times cited : (75)

References (51)
  • 1
    • 84875261622 scopus 로고    scopus 로고
    • Indoleamine 2,3 dioxygenase and metabolic control of immune responses
    • Munn, D. H.; Mellor, A. L. Indoleamine 2,3 dioxygenase and metabolic control of immune responses Trends Immunol. 2013, 34, 137-143 10.1016/j.it.2012.10.001
    • (2013) Trends Immunol. , vol.34 , pp. 137-143
    • Munn, D.H.1    Mellor, A.L.2
  • 2
    • 84926652188 scopus 로고    scopus 로고
    • Tryptophan-degrading enzymes in tumoral immune resistance
    • van Baren, N.; Van den Eynde, B. J. Tryptophan-degrading enzymes in tumoral immune resistance Front. Immunol. 2015, 6, 34 10.3389/fimmu.2015.00034
    • (2015) Front. Immunol. , vol.6 , pp. 34
    • Van Baren, N.1    Van Den Eynde, B.J.2
  • 3
    • 63849112500 scopus 로고    scopus 로고
    • The role of indoleamine 2,3-dioxygenase in the induction of immune tolerance: Focus on hematology
    • Curti, A.; Trabanelli, S.; Salvestrini, V.; Baccarani, M.; Lemoli, R. M. The role of indoleamine 2,3-dioxygenase in the induction of immune tolerance: focus on hematology Blood 2009, 113, 2394-2401 10.1182/blood-2008-07-144485
    • (2009) Blood , vol.113 , pp. 2394-2401
    • Curti, A.1    Trabanelli, S.2    Salvestrini, V.3    Baccarani, M.4    Lemoli, R.M.5
  • 4
    • 19344377474 scopus 로고    scopus 로고
    • GCN2 kinase in T cells mediates proliferative arrest and anergy induction in response to indoleamine 2,3-dioxygenase
    • Munn, D. H.; Sharma, M. D.; Baban, B.; Harding, H. P.; Zhang, Y.; Ron, D.; Mellor, A. L. GCN2 kinase in T cells mediates proliferative arrest and anergy induction in response to indoleamine 2,3-dioxygenase Immunity 2005, 22, 633-642 10.1016/j.immuni.2005.03.013
    • (2005) Immunity , vol.22 , pp. 633-642
    • Munn, D.H.1    Sharma, M.D.2    Baban, B.3    Harding, H.P.4    Zhang, Y.5    Ron, D.6    Mellor, A.L.7
  • 5
    • 34848915783 scopus 로고    scopus 로고
    • Plasmacytoid dendritic cells from mouse tumor-draining lymph nodes directly activate mature Tregs via indoleamine 2,3-dioxygenase
    • Sharma, M. D.; Baban, B.; Chandler, P.; Hou, D.-Y.; Singh, N.; Yagita, H.; Azuma, M.; Blazar, B. R.; Mellor, A. L.; Munn, D. H. Plasmacytoid dendritic cells from mouse tumor-draining lymph nodes directly activate mature Tregs via indoleamine 2,3-dioxygenase J. Clin. Invest. 2007, 117, 2570-2582 10.1172/JCI31911
    • (2007) J. Clin. Invest. , vol.117 , pp. 2570-2582
    • Sharma, M.D.1    Baban, B.2    Chandler, P.3    Hou, D.-Y.4    Singh, N.5    Yagita, H.6    Azuma, M.7    Blazar, B.R.8    Mellor, A.L.9    Munn, D.H.10
  • 6
    • 0142137237 scopus 로고    scopus 로고
    • Evidence for a tumoral immune resistance mechanism based on tryptophan degradation by indoleamine 2,3-dioxygenase
    • Uyttenhove, C.; Pilotte, L.; Théate, I.; Stroobant, V.; Colau, D.; Parmentier, N.; Boon, T.; Van den Eynde, B. J. Evidence for a tumoral immune resistance mechanism based on tryptophan degradation by indoleamine 2,3-dioxygenase Nat. Med. 2003, 9, 1269-1274 10.1038/nm934
    • (2003) Nat. Med. , vol.9 , pp. 1269-1274
    • Uyttenhove, C.1    Pilotte, L.2    Théate, I.3    Stroobant, V.4    Colau, D.5    Parmentier, N.6    Boon, T.7    Van Den Eynde, B.J.8
  • 7
    • 81255138408 scopus 로고    scopus 로고
    • Indoleamine 2,3-dioxygenase expression in human cancers: Clinical and immunologic perspectives
    • Godin-Ethier, J.; Hanafi, L. A.; Piccirillo, C. A.; Lapointe, R. Indoleamine 2,3-dioxygenase expression in human cancers: clinical and immunologic perspectives Clin. Cancer Res. 2011, 17, 6985-6991 10.1158/1078-0432.CCR-11-1331
    • (2011) Clin. Cancer Res. , vol.17 , pp. 6985-6991
    • Godin-Ethier, J.1    Hanafi, L.A.2    Piccirillo, C.A.3    Lapointe, R.4
  • 8
    • 16244408626 scopus 로고    scopus 로고
    • Inhibition of indoleamine 2,3-dioxygenase, an immunoregulatory target of the cancer suppression gene Bin1, potentiates cancer chemotherapy
    • Muller, A. J.; DuHadaway, J. B.; Donover, P. S.; Sutanto-Ward, E.; Prendergast, G. C. Inhibition of indoleamine 2,3-dioxygenase, an immunoregulatory target of the cancer suppression gene Bin1, potentiates cancer chemotherapy Nat. Med. 2005, 11, 312-319 10.1038/nm1196
    • (2005) Nat. Med. , vol.11 , pp. 312-319
    • Muller, A.J.1    DuHadaway, J.B.2    Donover, P.S.3    Sutanto-Ward, E.4    Prendergast, G.C.5
  • 9
    • 33846689594 scopus 로고    scopus 로고
    • Inhibition of indoleamine 2,3-dioxygenase in dendritic cells by stereoisomers of 1-methyl-tryptophan correlates with antitumor responses
    • Hou, D.-Y.; Muller, A. J.; Sharma, M. D.; DuHadaway, J. B.; Banerjee, T.; Johnson, M.; Mellor, A. L.; Prendergast, G. C.; Munn, D. H. Inhibition of indoleamine 2,3-dioxygenase in dendritic cells by stereoisomers of 1-methyl-tryptophan correlates with antitumor responses Cancer Res. 2007, 67, 792-801 10.1158/0008-5472.CAN-06-2925
    • (2007) Cancer Res. , vol.67 , pp. 792-801
    • Hou, D.-Y.1    Muller, A.J.2    Sharma, M.D.3    DuHadaway, J.B.4    Banerjee, T.5    Johnson, M.6    Mellor, A.L.7    Prendergast, G.C.8    Munn, D.H.9
  • 12
    • 84946425042 scopus 로고    scopus 로고
    • Challenges in the Discovery of Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors
    • references herein. DOI
    • Röhrig, U. F.; Majjigapu, S. R.; Vogel, P.; Zoete, V.; Michielin, O. Challenges in the Discovery of Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors. J. Med. Chem. 2015, and references herein. DOI: 10.1021/acs.jmedchem.5b00326.
    • (2015) J. Med. Chem.
    • Röhrig, U.F.1    Majjigapu, S.R.2    Vogel, P.3    Zoete, V.4    Michielin, O.5
  • 13
    • 84884545929 scopus 로고    scopus 로고
    • Indoleamine 2,3-dioxygenase inhibitors: A patent review
    • references herein
    • Dolušić, E.; Frédérick, R. Indoleamine 2,3-dioxygenase inhibitors: a patent review Expert Opin. Ther. Pat. 2013, 23, 1367-1381 and references herein. 10.1517/13543776.2013.827662
    • (2013) Expert Opin. Ther. Pat. , vol.23 , pp. 1367-1381
    • Dolušić, E.1    Frédérick, R.2
  • 14
    • 84939977228 scopus 로고    scopus 로고
    • Targeting key dioxygenases in tryptophan-kynurenine metabolism for immunomodulation and cancer chemotherapy
    • references herein
    • Austin, C. J.; Rendina, L. M. Targeting key dioxygenases in tryptophan-kynurenine metabolism for immunomodulation and cancer chemotherapy Drug Discovery Today 2015, 20, 609-617 and references herein. 10.1016/j.drudis.2014.11.007
    • (2015) Drug Discovery Today , vol.20 , pp. 609-617
    • Austin, C.J.1    Rendina, L.M.2
  • 16
    • 16244408626 scopus 로고    scopus 로고
    • Inhibition of indoleamine 2,3-dioxygenase, an immunoregulatory target of the cancer suppression gene bin1, potentiates cancer chemotherapy
    • Muller, A. J.; DuHadaway, J. B.; Donover, P. S.; Sutanto-Ward, E.; Prendergast, G. C. Inhibition of indoleamine 2,3-dioxygenase, an immunoregulatory target of the cancer suppression gene bin1, potentiates cancer chemotherapy Nat. Med. 2005, 11, 312-319 10.1038/nm1196
    • (2005) Nat. Med. , vol.11 , pp. 312-319
    • Muller, A.J.1    DuHadaway, J.B.2    Donover, P.S.3    Sutanto-Ward, E.4    Prendergast, G.C.5
  • 18
    • 42949087977 scopus 로고    scopus 로고
    • Synthesis of indoleamine 2,3-dioxygenase inhibitory analogues of the sponge alkaloid exiguamine A
    • Carr, G.; Chung, M. K. W.; Mauk, A. G.; Andersen, R. J. Synthesis of indoleamine 2,3-dioxygenase inhibitory analogues of the sponge alkaloid exiguamine A J. Med. Chem. 2008, 51, 2634-2637 10.1021/jm800143h
    • (2008) J. Med. Chem. , vol.51 , pp. 2634-2637
    • Carr, G.1    Chung, M.K.W.2    Mauk, A.G.3    Andersen, R.J.4
  • 21
    • 84876836937 scopus 로고    scopus 로고
    • Aminophenoxazinones as Inhibitors of Indoleamine 2,3-Dioxygenase (IDO). Synthesis of Exfoliazone and Chandrananimycin A
    • Pasceri, R.; Siegel, D.; Ross, D.; Moody, C. J. Aminophenoxazinones as Inhibitors of Indoleamine 2,3-Dioxygenase (IDO). Synthesis of Exfoliazone and Chandrananimycin A J. Med. Chem. 2013, 56, 3310-3317 10.1021/jm400049z
    • (2013) J. Med. Chem. , vol.56 , pp. 3310-3317
    • Pasceri, R.1    Siegel, D.2    Ross, D.3    Moody, C.J.4
  • 22
    • 84887959515 scopus 로고    scopus 로고
    • Discovery of Tryptanthrin Derivatives as Potent Inhibitors of Indoleamine 2,3-Dioxygenase with Therapeutic Activity in Lewis Lung Cancer (LLC) Tumor-Bearing Mice
    • Yang, S.; Li, X.; Hu, F.; Li, Y.; Yang, Y.; Yan, J.; Kuang, C.; Yang, Q. Discovery of Tryptanthrin Derivatives as Potent Inhibitors of Indoleamine 2,3-Dioxygenase with Therapeutic Activity in Lewis Lung Cancer (LLC) Tumor-Bearing Mice J. Med. Chem. 2013, 56, 8321-8331 10.1021/jm401195n
    • (2013) J. Med. Chem. , vol.56 , pp. 8321-8331
    • Yang, S.1    Li, X.2    Hu, F.3    Li, Y.4    Yang, Y.5    Yan, J.6    Kuang, C.7    Yang, Q.8
  • 23
    • 84947863491 scopus 로고    scopus 로고
    • Synthesis and Intracellular Redox Cycling of Natural Quinones and Their Analogues and Identification of Indoleamine-2,3-dioxygenase (IDO) as Potential Target for Anticancer Activity
    • Blunt, C. E.; Torcuk, C.; Liu, Y.; Lewis, W.; Siegel, D.; Ross, D.; Moody, C. J. Synthesis and Intracellular Redox Cycling of Natural Quinones and Their Analogues and Identification of Indoleamine-2,3-dioxygenase (IDO) as Potential Target for Anticancer Activity Angew. Chem., Int. Ed. 2015, 54, 8740-8745 10.1002/anie.201503323
    • (2015) Angew. Chem., Int. Ed. , vol.54 , pp. 8740-8745
    • Blunt, C.E.1    Torcuk, C.2    Liu, Y.3    Lewis, W.4    Siegel, D.5    Ross, D.6    Moody, C.J.7
  • 25
    • 80054920221 scopus 로고    scopus 로고
    • Structure-activity relationship and enzyme kinetic studies on 4-aryl-1H-1,2,3-triazoles as indoleamine 2,3-dioxygenase (IDO) inhibitors
    • Huang, Q.; Zheng, M.; Yang, S.; Kuang, C.; Yu, C.; Yang, Q. Structure-activity relationship and enzyme kinetic studies on 4-aryl-1H-1,2,3-triazoles as indoleamine 2,3-dioxygenase (IDO) inhibitors Eur. J. Med. Chem. 2011, 46, 5680-5687 10.1016/j.ejmech.2011.08.044
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 5680-5687
    • Huang, Q.1    Zheng, M.2    Yang, S.3    Kuang, C.4    Yu, C.5    Yang, Q.6
  • 32
    • 77955656666 scopus 로고    scopus 로고
    • S-benzylisothiourea derivatives as small-molecule inhibitors of indoleamine-2,3-dioxygenase
    • Matsuno, K.; Takai, K.; Isaka, Y.; Unno, Y.; Sato, M.; Takikawa, O.; Asai, A. S-benzylisothiourea derivatives as small-molecule inhibitors of indoleamine-2,3-dioxygenase Bioorg. Med. Chem. Lett. 2010, 20, 5126-5129 10.1016/j.bmcl.2010.07.025
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 5126-5129
    • Matsuno, K.1    Takai, K.2    Isaka, Y.3    Unno, Y.4    Sato, M.5    Takikawa, O.6    Asai, A.7
  • 33
    • 81755161497 scopus 로고    scopus 로고
    • Purification and kinetic characterization of human indoleamine 2,3-dioxygenase 1 and 2 (IDO1 and IDO2) and discovery of selective IDO1 inhibitors
    • Meininger, D.; Zalameda, L.; Liu, Y.; Stepan, L. P.; Borges, L.; McCarter, J. D.; Sutherland, C. L. Purification and kinetic characterization of human indoleamine 2,3-dioxygenase 1 and 2 (IDO1 and IDO2) and discovery of selective IDO1 inhibitors Biochim. Biophys. Acta, Proteins Proteomics 2011, 1814, 1947-1954 10.1016/j.bbapap.2011.07.023
    • (2011) Biochim. Biophys. Acta, Proteins Proteomics , vol.1814 , pp. 1947-1954
    • Meininger, D.1    Zalameda, L.2    Liu, Y.3    Stepan, L.P.4    Borges, L.5    McCarter, J.D.6    Sutherland, C.L.7
  • 34
    • 84907902924 scopus 로고    scopus 로고
    • Crystal structures and structure-activity relationships of imidazothiazole derivatives as IDO1 inhibitors
    • Tojo, S.; Kohno, T.; Tanaka, T.; Kamioka, S.; Ota, Y.; Ishii, T.; Kamimoto, K.; Asano, S.; Isobe, Y. Crystal structures and structure-activity relationships of imidazothiazole derivatives as IDO1 inhibitors ACS Med. Chem. Lett. 2014, 5, 1119-1123 10.1021/ml500247w
    • (2014) ACS Med. Chem. Lett. , vol.5 , pp. 1119-1123
    • Tojo, S.1    Kohno, T.2    Tanaka, T.3    Kamioka, S.4    Ota, Y.5    Ishii, T.6    Kamimoto, K.7    Asano, S.8    Isobe, Y.9
  • 35
    • 84955113400 scopus 로고    scopus 로고
    • See https://www.clinicaltrials.gov/.
  • 48
    • 33749019472 scopus 로고    scopus 로고
    • A facile and efficient synthesis of aryl toluenesulfonhydrazides and aryl toluenesulfonates under solvent-free conditions
    • Zhao, N.; Li, Y.; Wang, Y.; Wang, J. A facile and efficient synthesis of aryl toluenesulfonhydrazides and aryl toluenesulfonates under solvent-free conditions J. Sulfur Chem. 2006, 27, 427-432 10.1080/17415990600863752
    • (2006) J. Sulfur Chem. , vol.27 , pp. 427-432
    • Zhao, N.1    Li, Y.2    Wang, Y.3    Wang, J.4
  • 49
    • 1642634633 scopus 로고    scopus 로고
    • Sulfonyl-phenyl-ureido benzamidines: A novel structural class of potent antimalarial agents
    • Leban, J.; Pegoraro, S.; Dormeyer, M.; Lanzer, M.; Aschenbrenner, A.; Kramer, B. Sulfonyl-phenyl-ureido benzamidines: a novel structural class of potent antimalarial agents Bioorg. Med. Chem. Lett. 2004, 14, 1979-1982 10.1016/j.bmcl.2004.01.083
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 1979-1982
    • Leban, J.1    Pegoraro, S.2    Dormeyer, M.3    Lanzer, M.4    Aschenbrenner, A.5    Kramer, B.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.