Synthesis, in vitro and in silico evaluation of l-tyrosine containing PPARα/γ dual agonists

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 3, 2007, Pages 1547-1555

  Kumar, Rakesh ^a   Ramachandran, Uma ^a   Khanna, Smriti ^a   Bharatam, Prasad V ^a   Raichur, Suryaprakash ^b   Chakrabarti, Ranjan ^b  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

^b DR REDDY'S LABORATORIES LTD   (India)

Author keywords

Dual agonists; l Tyrosine; Molecular docking; PPAR; Transactivation

Indexed keywords

2 (1 METHYL 3 OXO 3 PHENYLPROPENYLAMINO) 3 [4 [2 (4 TRIFLUOROMETHYLPHENYL)ETHOXY]PHENYL]PROPIONIC ACID; 2 (2 BENZOYLCYCLOHEX 1 ENYLAMINO) 3 [4 (2 CARBAZOL 9 YLETHOXY)PHENYL] PROPIONIC ACID; 2 (2 BENZOYLCYCLOHEX 1 ENYLAMINO) 3 [4 [2 (9H CARBAZOL 4 YLOXY)ETHOXY]PHENYL]PROPIONIC ACID; 3 [4 (2 CARBAZOL 9 YLETHOXY)PHENYL] 2 (1 METHYL 3 OXO 3 PHENYLPROPENYLAMINO)PROPIONIC ACID; 3 [4 [2 (2,8 BISTRIFLUOROMETHYLQUINOLIN 4 YLOXY)ETHOXY]PHENYL] 2 (1 METHYL 3 OXO 3 PHENYLPROPENYLAMINO)PROPIONIC ACID; 3 [4 [2 (9H CARBAZOL 2 YLOXY)ETHOXY]PHENYL] 2 (1 METHYL 3 OXO 3 PHENYLPROPENYLAMINO)PROPIONIC ACID; 3 [4 [2 (9H CARBAZOL 4 YLOXY)ETHOXY]PHENYL] 2 (1 METHYL 3 OXO 3 PHENYLPROPENYLAMINO)PROPIONIC ACID; 3 [4 [2 [4 (4 CHLOROBENZOYL)PHENOXY]ETHOXY]PHENYL] 2 (1 METHYL 3 OXO 3 PHENYLPROPENYLAMINO)PROPIONIC ACID; 3 [4 [3 (9H CARBAZOL 4 YLOXY)PROPOXY]PHENYL] 2 (1 METHYL 3 OXO 3 PHENYLPROPENYLAMINO)PROPIONIC ACID; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA AGONIST; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST; PIRINIXIC ACID; ROSIGLITAZONE; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; TRANSACTIVATION;

COMPUTATIONAL BIOLOGY; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PPAR ALPHA; PPAR GAMMA; STRUCTURE-ACTIVITY RELATIONSHIP; TYROSINE;

EID: 33846027478     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.06.063     Document Type: Article

References (27)

1. Joe M.C., and Arshag D.M. Drugs 60 (2000) 95
2. Rotella D.P. J. Med. Chem. 47 (2004) 4111
3. Ramarao P., and Kaul C.L. Drugs Today 35 (1999) 895
4. Skyler J.S. J. Med. Chem. 47 (2004) 4113
5. Willson T.M., Brown P.J., Sternbach D.D., and Henke B.R. J. Med. Chem. 43 (2000) 527
6. Adams A.D., Yuen W., Hu Z., Santini C., Jones A.B., MacNaul K.L., Berger J.P., Doebber T.W., and Moller D.E. Bioorg. Med. Chem. Lett. 13 (2003) 931
7. Kasuga J., Hashimoto Y., and Miyachi H. Bioorg. Med. Chem. Lett. 16 (2006) 771
8. Kasuga J., Makishima M., Hashimoto Y., and Miyachi H. Bioorg. Med. Chem. Lett. 16 (2006) 554
9. Miller A.R., and Etgen G.J. Expert. Opin. Investig. Drugs 12 (2003) 1489
10. Nomura M., Tanase T., Ide T., Tsunoda M., Suzuki M., Uchiki H., Murakami K., and Miyachi H. J. Med. Chem. 46 (2003) 3581
11. Liu K., Xu L., Berger J.P., MacNaul K.L., Zhou G., Doebber T.W., Forrest M.J., Moller D.E., and Jones A.B. J. Med. Chem. 48 (2005) 2262
12. Koyama H., Miller D.J., Boueres J.K., Desai R.C., Jones A.B., Berger J.P., MacNaul K.L., Kelly L.J., Doebber T.W., Wu M.S., Zhou G., Wang P., Ippolito M.C., Chao Y.S., Agarwal A.K., Franklin R., Heck J.V., Wright S.D., Moller D.E., and Sahoo S.P. J. Med. Chem. 47 (2004) 3255
13. Lohray B.B., Lohray V.B., Bajji A.K., Kalchar S., Poondra R.R., Padakanti S., Chakrabarti R., Vikramdithyan R.K., Misra P., Juluri S., Rao N.V.S.M., and Rajagopalan R. J. Med. Chem. 44 (2001) 2675
14. Chakrabarti R., Misra P., Vikramadithyan R.K., Premkumar M., Hiriyan J., Datla S.R., Damarla R.K.B., Suresh J., and Rajagopalan R. Eur. J. Pharmacol. 491 (2004) 195
15. Henke B.R. J. Med. Chem. 47 (2004) 4118
16. Ramachandran U., Kumar R., and Mittal A. Mini-Rev. Med. Chem. 6 (2006) 563
17. Nolte R.T., Wisley G.B., Westin S., Cobb J.E., Lambert M.H., Kurokawa R., Rosenfeld M.G., Willson T.M., Glass C.K., and Milburn M.V. Nature 395 (1998) 137
18. Cronet P., Petersen J.F.W., Folmer R., Blomberg N., Sjoblom K., Karlsson U., Lindstedt E.-L., and Bamberg K. Structure 9 (2001) 699
19. Kumar R., Ramachandran U., Srinivasan K., Rao P.R., Raichur S., and Chakrabarti R. Bioorg. Med. Chem. 13 (2005) 4279
20. Ramachandran, U.; Kumar, R.; Mital, A.; Ramarao, P.; Srinivasan, K.; Dey, C. S.; Ishrath, A.; Chawla, H. P. S.; Kaul, C. L.; WTO Patent 2003, DEL/1268.
21. Kaneto H., Kajimoto Y., Miyagawa J., Matsuoka T., Fujitani Y., Umayahara Y., Hanafusa T., Matsuzawa Y., Yamasaki Y., and Hori M. Diabetes 48 (1999) 2398
22. Henke B.R., Blanchard S.G., Brackeen M.F., Brown K.K., Lehmann J.M., Parks D.J., Collins J.L., and Willson T.M. J. Med. Chem. 41 (1998) 5020
23. Collins J.L., Blanchard S.G., Boswell G.E., Parks D.J., Tong W.Q., and Lenhard J.M. J. Med. Chem. 41 (1998) 5037
24. Cobb J.E., Blanchard S.G., Brown K.K., Cooper J.P., Oliver W., Parks D.J., and Tong W.Q. J. Med. Chem. 41 (1998) 5055
25. Roman, D.; Andrew, K. WO 2001, 01/57001A1.
26. Khanna S., Sobhia M.E., and Bharatam P.V. J. Med. Chem. 48 (2005) 3015
27. Chakrabarti R., Vikramadithyan R.K., Misra P., Hiriyan J., Suryaprakash R., Damarla R.K., Cynthia G., Suresh J., and Rajagopalan R. Br. J. Pharmacol. 140 (2003) 527