Synthesis of (aryloxyacetylamino)-isonicotinic/nicotinic acid analogues as potent hypoxia-inducible factor (HIF)-1α inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 22, 2007, Pages 6305-6310

  Boovanahalli, Shanthaveerappa K ^a   Jin, Xuejun ^a   Jin, Yinglan ^a   Kim, Jin Hwan ^a   Dat, Nguyen Tien ^a   Hong, Young Soo ^a   Lee, Jeong Hyung ^a,b   Jung, Sang Hun ^c   Lee, Kyeong ^a   Lee, Jung Joon ^a  

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

^b Kangwon National University   (South Korea)

^c Chungnam National University   (South Korea)

Author keywords

HIF 1; HIF inhibitor; Hypoxia; Hypoxia inducible factor; Isonicotinic nicotinic acid analogues

Indexed keywords

ACETIC ACID DERIVATIVE; AMINE; ERYTHROPOIETIN; GLYCERALDEHYDE 3 PHOSPHATE DEHYDROGENASE; HYPOXIA INDUCIBLE FACTOR 1ALPHA; ISONICOTINIC ACID; NICOTINIC ACID DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; VASCULOTROPIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; EPO GENE; GENE; GENE TARGETING; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; STRUCTURE ACTIVITY RELATION; VEGF GENE; WESTERN BLOTTING;

CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; HYPOXIA-INDUCIBLE FACTOR 1, ALPHA SUBUNIT; ISONICOTINIC ACIDS; MOLECULAR STRUCTURE; NEOPLASMS; NIACIN;

EID: 35148841507     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.09.005     Document Type: Article

References (40)

1. Jones M.K., Szabo I.L., Kawanaka H., Husain S.S., and Tarnawski A.S. FASEB J. 16 (2002) 264
2. Wang G.L., Jiang B., Rue E.A., and Semenza G.L. Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 5510
3. Maxwell P.H., Dachs G.U., Gleadle J.M., Nicholls L.G., Harris A.L., Stratford I.J., Hankinson O., Pugh C.W., and Ratcliffe P.J. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 8104
4. Semenza G.L. Annu. Rev. Cell Dev. Biol. 15 (1999) 551
5. Jaakkola P., Mole D.R., Tian Y.-M., Wilson M.I., Gielbert J., Gaskell S.J., von Kriegsheim A., Hebestreit H.F., Mukherji M., Schofield C.J., Maxwell P.H., Pugh C.W., and Ratcliffe P.J. Science 292 (2001) 468
6. Semenza G.L. Trends Mol. Med. 8 (2002) S62
7. Harris A.L. Nat. Rev. Cancer 2 (2002) 38
8. Hickey M.M., and Simon C. Curr. Top. Dev. Biol. 76 (2006) 217
9. Carroll V.A., and Ashcroft M. Cancer Res. 66 (2006) 6264
10. Tian H., and McKnight S.L. Genes Dev. 11 (1997) 72
11. Makino Y., Kanopka A., Wilson W.J., Tanaka H., and Poellinger L. J. Biol Chem. 277 (2002) 39192
12. Zhong H., De Marzo A.M., Laughner E., Lim M., Hilton D.A., Zagzag D., Buechler P., Isaacs W.B., Semenza G.L., and Simons J.W. Cancer Res. 59 (1999) 5830
13. Birner P., Schindl M., Obermair A., Plank C., Breitenecker G., and Oberhuber G. Cancer Res. 60 (2000) 4693
14. Maxwell P.H., Dachs G.U., Gleadle J.M., Nicholls L.G., Harris A.L., Stratford I.J., Hankinson O., Pugh C.W., and Ratcliffe P.J. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 8104
15. Giaccia A., Siim B.G., and Johnson R.S. Nat. Rev. Drug Discov. 2 (2003) 1
16. Semenza G.L. Nat. Rev. Cancer 3 (2003) 721
17. Belozerov A.E., and Van Meir R.G. Anti-Cancer Drugs 16 (2005) 901
18. Rapisarda A., Uranchimeg B., Scudiero D.A., Selby M., Sausville E.A., Shoemaker R.H., and Melillo G. Cancer Res. 62 (2002) 4316
19. Shoemaker R.H., Scudiero D.A., Melillo G., Currens M.J., Monks A.P., Rabow A.A., Covell D.G., and Sausville E.A. Curr. Top. Med. Chem. 2 (2002) 229
20. YC-1: a potential anticancer drug targeting hypoxia-inducible factor 1. Yeo E.J., Chun Y.S., Cho Y.S., Kim J., Lee J.C., Kim M.S., and Park J.W. J. Natl. Cancer Inst. 95 (2003) 516
21. Isaacs J.S., Jung Y.J., Mimnaugh E.G., Martinez A., Cuttitta F., and Neckers L.M. J. Biol. Chem. 277 (2002) 29936
22. Mabjeesh N.J., Post D.E., Willard M.T., Kaur B., Van Meir E.G., Simons J.W., and Zhong H. Cancer Res. 62 (2002) 2478
23. Zagzag D., Nomura M., Friedlander D.R., Blanco C.Y., Gagner J.P., Nomura N., and Newcomb E.W. J. Cell. Physiol. 196 (2003) 394
24. Mabjeesh N.J., Escuin D., LaVallee T.M., Pribluda V.S., Swartz G.M., Johnson M.S., Willard M.T., Zhong H., Simons J.W., and Giannakakou P. Cancer Cell 3 (2003) 363
25. Welsh S.J., Williams R.R., Birmingham A., Newman D.J., Kirkpatrick D.L., and Powis G. Mol. Cancer Ther. 2 (2003) 235
26. Majumder P.K., Febbo P.G., Bikoff R., Berger R., Xue Q., McMahon L.M., Manola J., Brugarolas J., McDonnell T.J., Golub T.R., Loda M., Lane H.A., and Sellers W.R. Nat. Med. 10 (2004) 594
27. Tan C., de Noronha R.G., Roecker A.J., Pyrzynska B., Khwaja F., Zhang Z., Zhang H., Teng Q., Nicholson A.C., Giannakakou P., Zhou W., Olson J.J., Pereira M.M., Nicolaou K.C., and Van Meir E.G. Cancer Res. 65 2 (2005) 605
28. Kung A.L., Zabludoff S.D., France D.S., Freedman S.J., Tanner E.A., Vieira A., Cornell-Kennon S., Lee J., Wang B., Wang J., Memmert K., Naegeli H.U., Petersen F., Eck M.J., Bair K.W., Wood A.W., and Livingston D.M. Cancer Cell 6 (2004) 33
29. Mole D.R., Schlemminger I., McNeill L.A., Hewitson K.S., Pugh C.W., Ratcliffe P.J., and Schofield C.J. Bioorg. Med. Chem. Lett. 13 (2003) 2677
30. Epstein A.C.R., Gleadle J.M., McNeill L.A., Hewitson K.S., O'Rourke J., Mole D.R., Mukherji M., Metzen E., Wilson M.I., Dhanda A., Tian Y.M., Masson N., Hamilton D.L., Jaakkola P., Barstead R., Hodgkin J., Maxwell P.H., Pugh C.W., Schofield C.J., and Ratcliffe P. J. Cell 107 (2001) 43
31. Elkins J.M., Hewitson K.S., McNeill L.A., Seibel J.F., Schlemminger I., Pugh C.W., Ratcliffe P.J., and Schofield C.J. J. Biol. Chem. 278 (2003) 1802
32. Schlemminger I., Mole D.R., McNeill L.A., Dhanda A., Hewitson K.S., Tian Y.-M., Ratcliffe P.J., Pugh C.W., and Schofield C.J. Bioorg. Med. Chem. Lett. 13 (2003) 1451
33. Namal C.W., Shengde W., Angelique B., Richard K., Justin Sheville., Sean R., Kevin Xu., Matthew Pokross., Artem G.E., Richard W., and Marlene M. Bioorg. Med. Chem. Lett. 16 (2006) 5598
34. Namal C.W., Shengde W., Angelique B., Richard K., Justin S., Ritu T.B., Sean R., a Kevin X., Matthew P., Songtao Z., Richard W., Marlene M., Artem G.E., and Stephen E. Bioorg. Med. Chem. Lett. 16 (2006) 5616
35. Lee K., Lee J.H., Boovanahalli S.K., Jin Y., Lee M., Jin X., Kim J.H., Hong Y.-S., Lee J.H., and Lee J.J. J. Med. Chem. 50 (2007) 1675-1684
36. R = 17.2 min).
37. Wagner G.K., Kotschenreuther D., Zimmermann W., and Laufer S.A. J. Org. Chem. 68 (2003) 4527
38. Deardy L.W., Korytsky O.L., and Rowe J.E. Aust. J. Chem. 35 (1982) 2025
39. All the assays were performed under standard assay conditions by employing hypoxic condition as described by. Cai X.F., Jin X., Lee D., Yang Y.T., Lee K., Hong Y.-S., Lee J.H., and Lee J.J. J. Nat. Prod. 69 (2006) 1095
40. Semenza G.L. Biochem. Pharmacol. 59 (2000) 47-53