Aminophenoxazinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). synthesis of exfoliazone and chandrananimycin A

Journal of Medicinal Chemistry

Volumn 56, Issue 8, 2013, Pages 3310-3317

  Pasceri, Raffaele ^a   Siegel, David ^b   Ross, David ^b   Moody, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1,8 DIMETHYL 3H PHENOXAZIN 3 ONE; 2 AMINO 1,9 DIMETHYL 3H PHENOXAZIN 3 ONE; 2 AMINO 3H PHENOXAZIN 3 ONE; 2 AMINO 8 [(TETRAHYDROPYRAN 2 YLOXY)METHYL] 3H PHENOXAZIN 3 ONE; 2 AMINO 8 HYDROXYMETHYL 3H PHENOXAZIN 3 ONE; 2 AMINO 8 METHYL 3H PHENOXAZIN 3 ONE; 2 AMINO 9 HYDROXY 3H PHENOXAZIN 3 ONE; 2 AMINOPHENOL; AMINOPHENOXAZINONE DERIVATIVE; CARBOXYLIC ACID; CHANDRANANIMYCIN A; CINNABARINIC ACID; DIMETHYL 2 AMINO 3 OXO 3H PHENOXAZINE 1,9 DICARBOXYLIC ACID; DIMETHYL 2 AMINO 4,6 DIMETHYL 3 OXO 3H PHENOXAZINE 1,9 DICARBOXYLIC ACID; EXFOLIAZONE; INDOLEAMINE 2,3 DIOXYGENASE; INDOLEAMINE 2,3 DIOXYGENASE INHIBITOR; METHYL 2 AMINO 3 OXO 8 [(TETRAHYDROPYRAN 2 YLOXY)METHYL] 3H PHENOXAZINE 1 CARBOXYLIC ACID; METHYL 2 AMINO 8 (HYDROXYMETHYL) 3 OXO 3H PHENOXAZINE 1 CARBOXYLIC ACID; PHENOXAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; INHIBITION KINETICS;

AMINOPHENOLS; HUMANS; INDOLEAMINE-PYRROLE 2,3,-DIOXYGENASE; OXAZINES;

EID: 84876836937     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400049z     Document Type: Article

References (38)

1. Hollstein, U. Actinomycin-chemistry and mechanism of action Chem. Rev. 1974, 74, 625-652
2. Imai, S.; Shimazu, A.; Furihata, K.; Hayakawa, Y.; Seto, H. Isolation and structure of a new phenoxazine antibiotic, exfoliazone, produced by Streptomyces exfoliatus J. Antibiot. 1990, 43, 1606-1607
3. Imai, S.; Noguchi, T.; Seto, H. Studies on cell-growth stimulating substances of low-molecular-weight. 2. Exfoliazone and lavanducyanin, potent growth-promoting substances of rat-liver cell-line, rln-8, produced by Streptomyces exfoliatus and Streptomyces aeriouvifer J. Antibiot. 1993, 46, 1232-1238
4. Ren, J.; Liu, D.; Tian, L.; Wei, Y.; Proksch, P.; Zeng, J.; Lin, W. Venezuelines A-G, new phenoxazine-based alkaloids and aminophenols from Streptomyces venezuelae and the regulation of gene target Nur77 Bioorg. Med. Chem. Lett. 2013, 23, 301-304
5. Gomes, P. B.; Nett, M.; Dahse, H.-M.; Sattler, I.; Martin, K.; Hertweck, C. Bezerramycins A-C, antiproliferative phenoxazinones from Streptomyces griseus featuring carboxy, carboxamide or nitrile substituents Eur. J. Org. Chem. 2010, 231-235
6. Gripenberg, J. Fungus Pigments. 8. The structure of cinnabarin and cinnabarinic acid Acta Chem. Scand. 1958, 12, 603-610
7. Gomes, P. B.; Nett, M.; Dahse, H.-M.; Hertweck, C. Pitucamycin: structural merger of a phenoxazinone with an epoxyquinone antibiotic J. Nat. Prod. 2010, 73, 1461-1464
8. Maskey, R. P.; Li, F. R. C.; Qin, S.; Fiebig, H. H.; Laatsch, H. Chandrananimycins A-C: production of novel anticancer antibiotics from a marine Actinomadura sp isolate M048 by variation of medium composition and growth conditions J. Antibiot. 2003, 56, 622-629
9. Thuy, T. T.; Lam, T. H.; Huong, N. T. T.; Nhung, L. T. H.; Ninh, P. T.; Anh, N. T. H.; Thao, T. T. P.; Sung, T. V. Natural phenoxazine alkaloids from Peristrophe bivalvis (L.) Merr Biochem. Syst. Ecol. 2012, 44, 205-207
10. Carr, G.; Tay, W.; Bottriell, H.; Andersen, S. K.; Mauk, A. G.; Andersen, R. J. Plectosphaeroic acids A, B, and C, indoleamine 2,3-dioxygenase inhibitors produced in culture by a marine isolate of the fungus Plectosphaerella cucumerina Org. Lett. 2009, 11, 2996-2999
11. Prendergast, G. C. Immune escape as a fundamental trait of cancer: focus on IDO Oncogene 2008, 27, 3889-3900
12. Botting, N. P. Chemistry and neurochemistry of the kynurenine pathway of tryptophan metabolism Chem. Soc. Rev. 1995, 401-412
13. Muller, A. J.; Scherle, P. A. Targeting the mechanisms of tumoral immune tolerance with small-molecule inhibitors Nature Rev. Cancer 2006, 6, 613-625
14. 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 Nature Med. 2005, 11, 312-319
15. Muller, A. J.; Prendergast, G. C. Marrying immunotherapy with chemotherapy: why say IDO? Cancer Res. 2005, 65, 8065-8068
16. Muller, A. J.; Prendergast, G. C. Indoleamine 2,3-dioxygenase in immune suppression and cancer Curr. Cancer Drug Targets 2007, 7, 31-40
17. Smith, C.; Chang, M. Y.; Parker, K. H.; Beury, D. W.; DuHadaway, J. B.; Flick, H. E.; Boulden, J.; Sutanto-Ward, E.; Soler, A. P.; Laury-Kleintop, L. D.; Mandik-Nayak, L.; Metz, R.; Ostrand-Rosenberg, S.; Prendergast, G. C.; Muller, A. J. IDO is a nodal pathogenic driver of lung cancer and metastasis development Cancer Discovery 2012, 2, 722-735
18. Vecsei, L.; Szalardy, L.; Fulop, F.; Toldi, J. Kynurenines in the CNS: recent advances and new questions Nature Rev. Drug Discovery 2013, 12, 64-82
19. Kumar, S.; Jaller, D.; Patel, B.; LaLonde, J. M.; DuHadaway, J. B.; Malachowski, W. P.; Prendergast, G. C.; Muller, A. J. Structure based development of phenylimidazole-derived inhibitors of indoleamine 2,3-dioxygenase J. Med. Chem. 2008, 51, 4968-4977
20. Kumar, S.; Malachowski, W. P.; DuHadaway, J. B.; LaLonde, J. M.; Carroll, P. J.; Jaller, D.; Metz, R.; Prendergast, G. C.; Muller, A. J. Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors J. Med. Chem. 2008, 51, 1706-1718
21. 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
22. Le Roes-Hill, M.; Goodwin, C.; Burton, S. Phenoxazinone synthase: what's in a name? Trends Biotechnol. 2009, 27, 248-258
23. Bruyneel, F.; Enaud, E.; Billottet, L.; Vanhulle, S.; Marchand-Brynaert, J. Regioselective synthesis of 3-hydroxyorthanilic acid and its biotransformation into a novel phenoxazinone dye by use of laccase Eur. J. Org. Chem. 2008, 72-79
24. Horvath, T.; Kaizer, J.; Speier, G. Functional phenoxazinone synthase models-kinetic studies on the copper-catalyzed oxygenation of 2-aminophenol J. Mol. Catal. A: Chem. 2004, 215, 9-15
25. Angyal, S. J.; Bullock, E.; Hanger, W. G.; Howell, W. C.; Johnson, A. W. Actinomycin. 3. The reaction of actinomycin with alkali J. Chem. Soc. 1957, 1592-1602
26. Ruan, J. W.; Huang, Z. S.; Huang, J. F.; Du, C. J.; Huang, S. L.; Shi, Z.; Fu, L. W.; Gu, L. Q. Synthesis of phenoxazinone derivatives and antiproliferative activities on wild-type and drug-resistant tumor cells Chin. Chem. Lett. 2006, 17, 1141-1144
27. Giurg, M.; Piekielska, K.; Gebala, M.; Ditkowski, B.; Wolanski, M.; Peczynska-Czoch, W.; Mlochowski, J. Catalytic oxidative cyclocondensation of o -aminophenols to 2-amino-3 H -phenoxazin-3-ones Synth. Commun. 2007, 37, 1779-1789
28. Hick, L. A.; Manthey, M. K.; Truscott, R. J. W. Triphenodioxazine-1,8- dicarboxylic acid as an oxidation-product of 3-hydroxyanthranilic acid J. Heterocycl. Chem. 1991, 28, 1157-1160
29. Tomoda, A.; Shirasawa, E.; Nagao, S.; Minami, M.; Yoneyama, Y. Involvement of oxidoreductive reactions of intracellular hemoglobin in the metabolism of 3-hydroxyanthranilic acid in human erythrocytes Biochem. J. 1984, 222, 755-760
30. Rao, P. V. S.; Jegannathan, N. S.; Vaidyanathan, C. S. Enzymic conversion of 3-hydroxyanthranilic acid into cinnabarinic acid by the nuclear fraction of rat liver Biochem. J. 1965, 95, 628-632
31. Mangin, D. R.; Sulsky, R. B.; Ridd, J. A.; Caulfield, T. J.; Parker, R. A. Dual inhibitors of adipocyte fatty acid binding protein and keratinocyte fatty acid binding protein. U.S. Patent US 2003/0225091 A1, 2003.
32. Huang, S.-T.; Hsei, I. J.; Chen, C. Synthesis and anticancer evaluation of bis(benzimidazoles), bis(benzoxazoles), and benzothiazoles Bioorg. Med. Chem. 2006, 14, 6106-6119
33. Weinstein, B.; Goodman, L.; Baker, B. R.; Crews, O. P.; Leaffer, M. A. Potential anticancer agents. 70. Some simple derivatives of actinomycins J. Org. Chem. 1962, 27, 1389-1395
34. Ausin, C.; Ortega, J. A.; Robles, J.; Grandas, A.; Pedroso, E. Synthesis of amino- and guanidino-G-clamp PNA monomers Org. Lett. 2002, 4, 4073-4075
35. Fishman, J. B. The condensation of formaldehyde with ortho -nitrophenol J. Am. Chem. Soc. 1920, 42, 2288-2297
36. Austin, C. J. D.; Mizdrak, J.; Matin, A.; Sirijovski, N.; Kosim-Satyaputra, P.; Willows, R. D.; Roberts, T. H.; Truscott, R. J. W.; Polekhina, G.; Parker, M. W.; Jamie, J. F. Optimised expression and purification of recombinant human indoleamine 2,3-dioxygenase Protein Express. Purif. 2004, 37, 392-398
37. Takikawa, O.; Kuroiwa, T.; Yamazaki, F.; Kido, R. Mechanism of interferon-gamma action-characterization of indoleamine 2,3-dioxygenase in cultured human-cells induced by interferon-gamma and evaluation of the enzyme-mediated tryptophan degradation in its anticellular activity J. Biol. Chem. 1988, 263, 2041-2048
38. Gaspari, P.; Banerjee, T.; Malachowski, W. P.; Muller, A. J.; Prendergast, G. C.; DuHadaway, J.; Bennett, S.; Donovan, A. M. Structure-activity study of brassinin derivatives as indoleamine 2,3-dioxygenase inhibitors J. Med. Chem. 2006, 49, 684-692