Exploration of secondary and tertiary pharmacophores in unsymmetrical N,N′-diaryl urea inhibitors of soluble epoxide hydrolase

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 9, 2010, Pages 2740-2744

  Anandan, Sampath Kumar ^a   Gless, Richard D ^a  

^a Arete Therapeutics Inc   (United States)

Author keywords

Metabolic syndrome; N,N Unsymmetrical diaryl urea; sEH inhibitor

Indexed keywords

ENZYME INHIBITOR; EPOXIDE HYDROLASE; EPOXIDE HYDROLASE INHIBITOR; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG SOLUBILITY; DRUG STRUCTURE; IC 50; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION;

ENZYME INHIBITORS; EPOXIDE HYDROLASES; MODELS, CHEMICAL; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP; UREA;

EID: 77950864854     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.03.074     Document Type: Article

References (35)

1. Spector A.A., Fang X., Snyder G.D., and Weintraub N.L. Prog. Lipid Res. 434 (2004) 55
2. Lason B.T., Gutterman D.D., and Hatoum O.A. Eur. J. Clin. Invest. 36 (2006) 293
3. Zhang L.-N., Vincelette J., Cheng Y., Mehra U., Chen D., Anandan S.-K., Gless R., Webb H.K., and Wang Y.-X. Arterioscler. Thromb. Vasc. Biol. 29 (2009) 1265
4. Ulu A., Davis B.B., Tsai H.-J., Kim I.-H., Morisseau C., Inceoglu B., Fiehn O., Hammock B.D., and Weiss R.H. J. Cardiovasc. Pharm. 52 (2008) 314
5. Jung O., Brandes R.P., Kim I., Schweda F., Schmidt R., Hammock B.D., Busse R., and Fleming I. Hypertension 45 (2005) 759
6. Imig J.D., Zhao X., Zaharis C.Z., Olearczyk J.J., Pollock D.M., Newman J.W., Kim I.-H., Watanabe T., and Hammock B.D. Hypertension 46 (2005) 975
7. Yu Z., Xu F., Huse L.M., Morisseau C., Draper A.J., Newman J.W., Parker C., Graham L., Engler M.M., Hammock B.D., Zeldin D.C., and Kroetz D.L. Circ. Res. 87 (2000) 992
8. Wong, K.; Zhang, L.-N.; Vincelette, J.; Chen, D.; Mehra, U.; Chen, Y.; Gless, R.; Anandan, S.-K.; Webb, H. K.; MacIntyre, E.; Wang, X.-Y. 'A Novel Inhibitor of Soluble Epoxide Hydrolase, AR9281, Improves Glucose Homeostasis in Diet-Induced Obese Mice' presented at the American Diabetes Association Meeting 69th Scientific Session, New Orleans, LA, June, 2009.
9. Xu D., Li N., He Y., Timofeyev V., Lu L., Tsai H.-J., Kim I.-H., Tuteja D., Mateo R.K.P., Singapuri A., Davis B.B., Low R., Hammock B.D., and Chiamvimonvat N. Proc. Nat. Acad. Sci. 103 (2006) 18733
10. Zhao X., Yamamoto T., Newman J.W., Kim I.-H., Watanabe T., Hammock B.D., Stewart J., Pollock J.S., Pollock D.M., and Imig J.D. J. Am. Soc. Nephrol. 15 (2004) 1244
11. Imig J.D. Am. J. Physiol. Renal Physiol. 289 (2005) F496
12. Dorrance A.M., Rupp N., Pollock D.M., Newman J.W., Hammock B.D., and Imig J.D. J. Cardiovasc. Pharm. 46 (2005) 842
13. Liu Y., Webb H., and Kroetz D.L. FASEB J. 22 (2008) 479.19
14. Parrish A.R., Chen G., Burghardt R.C., Watanabe T., Morisseau C., and Hammock B.D. Cell. Biol. Toxicol. 25 (2009) 217
15. Node K., Huo Y., Ruan X., Yang B., Spiecker M., Ley K., Zeldin D.C., and Liao J.K. Science 285 (1999) 1276
16. Schmelzer K.R., Kubala L., Newman J.W., Kim I.-H., Eiserich J.P., and Hammock B.D. Proc. Nat. Acad. Sci. 102 (2005) 9772
17. Smith K.R., Pinkerton K.E., Watanabe T., Pedersen T.L., Ma S.J., and Hammock B.D. Proc. Nat. Acad. Sci. 102 (2005) 2186
18. Govindarajan G., Whaley-Connell A., Mugo M., Stump C., and Sowers J.R. Am. J. Med. Sci. 330 (2005) 311
19. http://www.aretetherapeutics.com.
20. Morisseau C., Goodrow M.H., Newman J.W., Wheelock C.E., Dowdy D.L., and Hammock B.D. Biochem. Pharmacol. 63 (2002) 1599
21. Kim I.-H., Nishi K., Tsai H.-J., Bradford T., Koda Y., Watanabe T., Morisseau C., Blanchfield J., Toth I., and Hammock B.D. Biorg. Med. Chem. Lett. 15 (2007) 312
22. Kim I.-H., Morisseau C., Watanabe T., and Hammock B.D. J. Med. Chem. 47 (2004) 2110
23. Kim I.-H., Heirtzler F.R., Morisseau C., Nishi K., Tsai H.-J., and Hammock B.D. J. Med. Chem. 48 (2005) 3621
24. Li H.-Y., Jin Y., Morisseau C., Hammock B.D., and Lon Y.-Q. Bioorg. Med. Chem. 14 (2006) 6586
25. Jones P.D., Tsai H.-J., Do Z.N., Morisseau C., and Hammock B.D. Biorg. Med. Chem. Lett. 16 (2006) 5212
26. Hwang S.H., Morisseau C., Do Z., and Hammock B.D. Bioorg. Med. Chem. Lett. 16 (2006) 5773
27. Hwang S.H., Tsai H.-J., Liu J.-K., Morisseau C., and Hammock B.D. J. Med. Chem. 50 (2007) 3825
28. Kim I.-H., Tsai H.-J., Nishi K., Kasagami T., Morisseau C., and Hammock B.D. J. Med. Chem. 50 (2007) 5217
29. Kasagami T., Kim I.-H., Tsai H.-J., Nishi K., Hammock B.D., and Morisseau C. Bioorg. Med. Chem. 19 (2009) 1784
30. Marino J.P. Curr. Top. Med. Chem. 9 (2009) 452
31. Shen H.C., Ding F.-X., Wang S., Xu S., Chen H.-S., Tong X., Tong V., Mitra K., Kumar S., Zhang X., Chen Y., Zhou G., Pai L.-Y., Alonso-Galicia M., Chen X., Zhang B., Tata J.R., Berger J.P., and Colletti S.L. Bioorg. Med. Chem. 19 (2009) 3398
32. Shen H.C., Ding F.-X., Wang S., Deng Q., Zhang X., Chen Y., Zhou G., Xu S., Chen H.-S., Tong X., Tong V., Mitra K., Kumar S., Tsai C., Stevenson A.S., Pai L.-Y., Alonso-Galicia M., Chen X., Soisson S.M., Roy S., Zhang B., Tata J.R., Berger J.P., and Colletti S.L. J. Med. Chem. 52 (2009) 5009
33. Eldrup A.B., Solewymanzadeh F., Taylor S.J., Muegge I., Farrow N.A., Joseph D., McKellop K., Man C.C., Kulkulka A., and Lombaert S.D. J. Med. Chem. 52 (2009) 5880
34. Anandan S.-K., Webb H.K., Do Z.N., and Gless R.D. Bioorg. Med. Chem. Lett. 19 (2009) 4259
35. 50 value of ca. 3 nM. Jones P.D., Wolf N.M., Morisseau C., Whetstone P., Hock B., and Hammock B.D. Anal. Biochem. 343 (2005) 66