Discovery of indenopyrazoles as a new class of hypoxia inducible factor (HIF)-1 inhibitors

ACS Medicinal Chemistry Letters

Volumn 4, Issue 2, 2013, Pages 297-301

  Minegishi, Hidemitsu ^a   Fukashiro, Shinji ^a   Ban, Hyun Seung ^a,b   Nakamura, Hiroyuki ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

^b Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

Author keywords

HIF 1; indenopyrazole; inhibitor; transcriptional activity

Indexed keywords

HETERODIMER; HYPOXIA INDUCIBLE FACTOR 1 INHIBITOR; HYPOXIA INDUCIBLE FACTOR 1ALPHA; HYPOXIA INDUCIBLE FACTOR 1BETA; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL; CELL STRAIN HCT116; CELL STRAIN HEPG2; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; FEMALE; HELA CELL; HUMAN; HUMAN CELL; IC 50; PRIORITY JOURNAL;

EID: 84873970182     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml3004632     Document Type: Article

References (32)

1. Semenza, G. L. Targeting HIF-1 for Cancer Therapy Nat. Rev. Cancer 2003, 3, 721-732
2. 2 tension Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 5510-5514
3. Wang, G. L.; Semenza, G. L. Purification and characterization of hypoxia-inducible Factor 1 J. Biol. Chem. 1995, 270, 1230-1237
4. 2-dependent degradation domain via the ubiquitin-proteasome pathway Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 7987-92
5. 2 Sensing Science 2001, 292, 464-468
6. Jiang, B.-H.; Rue, E.; Wang, G. L.; Roe, R.; Semenza, G. L. Dimerization, DNA Binding, and Transactivation Properties of Hypoxia-inducible Factor 1 J. Biol. Chem. 1996, 271, 17771-17778
7. Zhong, H.; De Marzo, A. M.; Laughner, E.; Lim, M.; Hilton, D. A.; Zagzag, D.; Buechler, P.; Isaacs, W. B.; Semenza, G. L.; Simons, J. W. Overexpression of Hypoxia-inducible Factor 1α in Common Human Cancers and Their Metastases Cancer Res. 1999, 59, 5830-5835
8. 2-regulated gene expression FASEB J. 2002, 16, 1151-1162
9. Talks, K. L.; Turley, H.; Gatter, K. C.; Maxwell, P. H.; Pugh, C. W.; Ratcliffe, P. J.; Harris, A. L. The Expression and Distribution of the Hypoxia-Inducible Factors HIF-1α and HIF-2α in Normal Human Tissues, Cancers, and Tumor-Associated Macrophages Am. J. Pathol. 2000, 157, 411-421
10. Birner, P.; Schindl, M.; Obermair, A.; Breitenecker, G.; Oberhuber, G. Expression of Hypoxia-inducible Factor 1α in Epithelial Ovarian Tumors: Its Impact on Prognosis and on Response to Chemotherapy Clin. Cancer Res. 2001, 7, 1661-1668
11. Birner, P.; Gatterbauer, B.; Oberhuber, G.; Schindl, M.; Rössler, K.; Prodinger, A.; Budka, H.; Hainfellner, J. A. Expression of hypoxia-inducible factor-1α in oligodendrogliomas: Its impact on prognosis and neoangiogenesis Cancer 2001, 92, 165-171
12. Giatromanolaki, A.; Koukourakis, M. I.; Sivridis, E.; Turley, H.; Talks, K.; Pezzella, F.; Gatter, K. C.; Harris, A. L. Relation of hypoxia inducible factor 1α and 2α in operable non-small cell lung cancer to angiogenic/molecular profile of tumours and survival Br. J. Cancer 2001, 85, 881-890
13. Zagzag, D.; Zhong, H.; Scalzitti, J. M.; Laughner, E.; Simons, J. W.; Semenza, G. L. Expression of hypoxia-inducible factor 1α in brain tumors: Association with angiogenesis, invasion, and progression Cancer 2000, 88, 2606-2618
14. Birner, P.; Schindl, M.; Obermair, A.; Plank, C.; Breitenecker, G.; Oberhuber, G. Overexpression of Hypoxia-inducible Factor 1α Is a Marker for an Unfavorable Prognosis in Early-Stage Invasive Cervical Cancer Cancer Res. 2000, 60, 4693-4696
15. Folkman, J. Angiogenesis: An organizing principle for drug discovery? Nat. Rev. Drug Discovery 2007, 6, 273-286
16. 2 availability on human cancer Nat. Rev. Cancer 2008, 8, 967-975
17. Ban, H. S.; Uto, Y.; Nakamura, H. Hypoxia-inducible factor inhibitors: A survey of recent patented compounds (2004-2010) Expert Opin. Ther. Pat. 2011, 21, 131-146
18. Koh, M. Y.; Spivak-Kroizman, T.; Venturini, S.; Welsh, S.; Williams, R. R.; Kirkpatrick, D. L.; Powis, G. Molecular mechanisms for the activity of PX-478, an antitumor inhibitor of the hypoxia-inducible factor-1α Mol. Cancer Ther. 2008, 7, 90-100
19. Le Cras, T. D.; Korfhagen, T. R.; Davidson, C.; Schmidt, S.; Fenchel, M.; Ikegami, M.; Whitsett, J. A.; Hardie, W. D. Inhibition of PI3K by PX-866 Prevents Transforming Growth Factor-α induced Pulmonary Fibrosis Am. J. Pathol. 2010, 176, 679-686
20. Greenberger, L. M.; Horak, I. D.; Filpula, D.; Sapra, P.; Westergaard, M.; Frydenlund, H. F.; Albæk, C.; Schrøder, H.; Ørum, H. A RNA antagonist of hypoxia-inducible factor-1α, EZN-2968, inhibits tumor cell growth Mol. Cancer Ther. 2008, 7, 3598-3608
21. Lee, K.; Lee, J. H.; Boovanahalli, S. K.; Jin, Y.; Lee, M.; Jin, X.; Kim, J. H.; Hong, Y.-S.; Lee, J. J. Aryloxyacetylamino)benzoic Acid Analogues: A New Class of Hypoxia-Inducible Factor-1 Inhibitors J. Med. Chem. 2007, 50, 1675-1684
22. Won, M.-S.; Im, N.; Park, S.; Boovanahalli, S. K.; Jin, Y.; Jin, X.; Chung, K.-S.; Kang, M.; Lee, K.; Park, S.-K.; Kim, H. M.; Kwon, B. M.; Lee, J. J.; Lee, K. A novel benzimidazole analogue inhibits the hypoxia-inducible factor (HIF)-1 pathway Biochem. Biophys. Res. Commun. 2009, 385, 16-21
23. Shimizu, K.; Maruyama, M.; Yasui, Y.; Minegishi, H.; Ban, H. S.; Nakamura, H. Boron-containing phenoxyacetanilide derivatives as hypoxia-inducible factor (HIF)-1α inhibitors Bioorg. Med. Chem. Lett. 2010, 20, 1453-1456
24. Ban, H. S.; Shimizu, K.; Minegishi, H.; Nakamura, H. Identification of HSP60 as a Primary Target of o -Carboranylphenoxyacetanilide, an HIF-1α Inhibitor J. Am. Chem. Soc. 2010, 132, 11870-11871
25. Ban, H. S.; Uno, M.; Nakamura, H. Suppression of hypoxia-induced HIF-1α accumulation by VEGFR inhibitors: Different profiles of AAL993 versus SU5416 and KRN633 Cancer Lett. 2010, 296, 17-26
26. Uno, M.; Ban, H. S.; Nakamura, H. 1-[4-(N -Benzylamino)phenyl]-3- phenylurea derivatives as a new class of hypoxia-inducible factor-1α inhibitors Bioorg. Med. Chem. Lett. 2009, 19, 3166-3169
27. Tang, J.; Luo, Z.; Zhou, G.; Song, C.; Yu, F.; Xiang, J.; Li, G. Cis-regulatory functions of overlapping HIF-1alpha/E-box/AP-1-like sequences of CD164 BMC Mol. Biol. 2011, 12, 44
28. Nugiel, D. A.; Vidwans, A.; Etzkorn, A.-M.; Rossi, K. A.; Benfield, P. A.; Burton, C. R.; Cox, S.; Doleniak, D.; Seitz, S. P. Synthesis and Evaluation of Indenopyrazoles as Cyclin-Dependent Kinase Inhibitors. 2. Probing the Indeno Ring Substituent Pattern J. Med. Chem. 2002, 45, 5224-5232
29. Ho, C. Y.; Ludovici, D. W.; Maharoof, U. S. M.; Mei, J.; Sechler, J. L.; Tuman, R. W.; Strobel, E. D.; Andraka, L.; Yen, H.-K.; Leo, G.; Li, J.; Almond, H.; Lu, H.; DeVine, A.; Tominovich, R. M.; Baker, J.; Emanuel, S.; Gruninger, R. H.; Middleton, S. A.; Johnson, D. L.; Galemmo, R. A. (6,7-Dimethoxy-2,4- dihydroindeno[1,2- c ]pyrazol-3-yl)phenylamines: Platelet-Derived Growth Factor Receptor Tyrosine Kinase Inhibitors with Broad Antiproliferative Activity against Tumor Cells J. Med. Chem. 2005, 48, 8163-8173
30. Hossain, C. F.; Kim, Y.-P.; Baerson, S. R.; Zhang, L.; Bruick, R. K.; Mohammed, K. A.; Agarwal, A. K.; Nagle, D. G.; Zhou, Y.-D. Saururus cernuus lignans-potent small molecule inhibitors of hypoxia-inducible factor-1 Biochem. Biophys. Res. Commun. 2005, 333, 1026-1033
31. Hanessian, S.; Reddy, G. J.; Chahal, N. Total Synthesis and Stereochemical Confirmation of Manassantin A, B, and B1 Org. Lett. 2006, 8, 5477-5480
32. Kim, H.; Kasper, A. C.; Moon, E. J.; Park, Y.; Wooten, C. M.; Dewhirst, M. W.; Hong, J. Nucleophilic Addition of Organozinc Reagents to 2-Sulfonyl Cyclic Ethers: Stereoselective Synthesis of Manassantins A and B Org. Lett. 2008, 11, 89-92