Design, synthesis, and docking studies of telmisartan analogs for the treatment of metabolic syndrome

Medicinal Chemistry Research

Volumn 18, Issue 8, 2009, Pages 611-628

  Mizuno, Cassia S ^a   Chittiboyina, Amar G ^a   Patny, Akshay ^a   Kurtz, Theodore W ^b   Pershadsingh, Harrihar A ^c,d   Speth, Robert C ^e   Karamyan, Vardan T ^e   Avery, Mitchell A ^a  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d Bethesda Pharmaceuticals Inc   (United States)

^e UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

AT1 antagonist; Hypertension; Metabolic syndrome; PPAR gamma; Telmisartan

Indexed keywords

4' [(1,7' DIMETHYL 2' PROPYL 1H,3'H 2,5' BIBENZO[D]IMIDAZOL 3' YL)METHYL]BIPHENYL 2,4 DICARBOXYLIC ACID; ANGIOTENSIN 1 RECEPTOR; DIMETHYL 4' [(1,7' DIMETHYL 2' PROPYL 1H,3'H 2,5' BIBENZO[D]IMIDAZOL 3' YL)METHYL]BIPHENYL 2,4 DICARBOXYLATE; MT 001; MT 002; MT 003; MT 003A; MT 004; MT 005; MT 006; MT 007; MT 008; MT 009; MT 010; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; ROSIGLITAZONE; TELMISARTAN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BINDING ASSAY; CONTROLLED STUDY; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; METABOLIC SYNDROME X; MOUSE; NONHUMAN;

EID: 70449518425     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-008-9153-9     Document Type: Article

References (21)

1. 1 receptor activation is dependent upon two juxtaposed asparagine residues on transmembrane helices III and VII Biol Chem 272 7 4245 4251 10.1074/jbc.272.7.4245 10.1074/jbc.272.7.4245 1:CAS:528:DyaK2sXht1Oksbo%3D (Pubitemid 27078494)
2. GA Bray FL Greenway 1999 Current and potential drugs for treatment of obesity Endocr Rev 20 805 875 10.1210/er.20.6.805 10.1210/er.20.6.805 1:CAS:528:DC%2BD3cXntV2iug%3D%3D 10605627
3. Chakravarty PK, Patchett AA, Camara VJ, Walsh TF, Greenlee WJ (1990) Preparation and formulation of benzimidazoles as angiotensin II antagonists. European patent 0400835A
4. TE Delea JS Edelsberg M Hagiwara G Oster LS Phillips 2003 Use of thiazolidinediones and risk of heart failure in people with type 2 diabetes: a retrospective cohort study Diabetes Care 26 2983 2989 10.2337/diacare.26.11.2983 10.2337/diacare.26.11.2983 1:CAS:528:DC%2BD3sXpsFert78%3D 14578227 (Pubitemid 37339487)
5. RH Eckel SM Grundy PZ Zimmet 2005 The metabolic syndrome Lancet 365 1415 1428 10.1016/S0140-6736(05)66378-7 10.1016/S0140-6736(05)66378-7 1:CAS:528:DC%2BD2MXjsVegtbg%3D 15836891 (Pubitemid 40523737)
6. CS Flordellis I Ilias AG Papavassiliou 2005 New therapeutic options for the metabolic syndrome: what's next? Trends End Metab 16 254 260 10.1016/j.tem.2005.06.001 10.1016/j.tem.2005.06.001 1:CAS:528: DC%2BD2MXmvVKnt7w%3D (Pubitemid 41058756)
7. SM Grundy HB Brewer Jr JI Cleeman SC Smith Jr C Lenfant 2004 Definition of metabolic syndrome: report of the National Heart, Lung, and Blood Institute/American Heart Association conference on scientific issues related to definition Circulation 109 433 438 10.1161/01.CIR.0000111245.75752.C6 10.1161/01.CIR.0000111245.75752.C6 14744958 (Pubitemid 38133916)
8. Harrold M (2002) Foye's principles of medicinal chemistry, 5th edn. Lippincott Williams & Wilkins, Philadelphia, pp 533-561
9. K-L Hoe JM Saavedra 2002 Site-directed mutagenesis of the gerbil and human angiotensin II AT1 receptors identifies amino acid residues attributable to the binding affinity for the nonpeptidic antagonist losartan Mol Pharmacol 61 1404 1415 10.1124/mol.61.6.1404 10.1124/mol.61.6.1404 1:CAS:528: DC%2BD38XksVWrtLo%3D 12021402 (Pubitemid 34575751)
10. BB Kahn JS Flier 2000 Obesity and insulin resistance J Clin Invest 106 473 481 10.1172/JCI10842 10.1172/JCI10842 1:CAS:528:DC%2BD3cXlvFCltbw%3D 10953022
11. FH Messerli 2002 Vasodilatory edema: a common side effect of antihypertensive therapy Curr Cardiol Rep 4 479 482 10.1007/s11886-002-0110-9 10.1007/s11886-002-0110-9 12379167
12. AH Mokdad ES Ford BA Bowman WH Dietz F Vinicor VS Bales JS Marks 2003 Prevalence of obesity, diabetes, and obesity-related health risk factors JAMA 289 76 79 10.1001/jama.289.1.76 10.1001/jama.289.1.76 12503980 (Pubitemid 36026281)
13. KMV Narayan JP Boyle TJ Thompson SW Sorensen DF Williamson 2003 Lifetime risk for diabetes mellitus in the United States JAMA 290 1884 1890 10.1001/jama.290.14.1884 10.1001/jama.290.14.1884 1:CAS:528:DC%2BD3sXotVWnsr4%3D 14532317 (Pubitemid 37430605)
14. Pascal R, Sola R, Labeguere F, Jouin P (2000) Synthesis of the novel amino acid 4-amino-3-(aminomethyl)benzoic acid (AmAbz) and its protected derivatives as building blocks for pseudopeptide synthesis. Eur J Org Chem 22:3755-3761. doi:10.1002/1099-0690(200011)2000:22<3755::AID-EJOC3755>3.0. CO;2-I
15. A Patny PV Desai MA Avery 2006 Ligand-supported homology modeling of the human angiotensin II type 1 (AT1) receptor: insights into the molecular determinants of telmisartan binding Proteins Struct Funct Bioinf 65 824 842 10.1002/prot.21196 10.1002/prot.21196 1:CAS:528:DC%2BD28Xht1eisLvO (Pubitemid 44772882)
16. UJ Ries G Mihm B Narr KM Hasselbach H Wittneben M Entzeroth JC van Meel W Wienen NH Hauel 1993 6-Substituted benzimidazoles as new nonpeptide angiotensin II receptor antagonists: synthesis, biological activity, and structure-activity relationships J Med Chem 36 4040 4051 10.1021/jm00077a007 10.1021/jm00077a007 1:CAS:528:DyaK2cXpsVOgsw%3D%3D 8258826 (Pubitemid 24024676)
17. AM Rouhi 2004 Metabolic syndrome Chem Eng News 82 83 99
18. RC Speth 2003 Sarcosine1, glycine8 angiotensin II is an AT1 angiotensin II receptor subtype selective antagonist Regul Pept 115 203 209 10.1016/S0167-0115(03)00172-1 10.1016/S0167-0115(03)00172-1 1:CAS:528: DC%2BD3sXnvVKqs70%3D 14556962 (Pubitemid 37211436)
19. RC Speth JW Harding 2001 Radiolabeling of angiotensin peptides Methods Mol Med 51 275 295 1:CAS:528:DC%2BD3cXot1Wru7c%3D
20. PFW Stouten C Frömmel H Nakamura C Sander 1993 An effective solvation term based on atomic occupancies for use in protein simulations Mol Simul 10 97 120 10.1080/08927029308022161 10.1080/08927029308022161 1:CAS:528:DyaK3sXmtF2rurY%3D
21. P Zimmet KGMM Alberti J Shaw 2001 Global and societal implications of the diabetes epidemic Nature 414 782 787 10.1038/414782a 10.1038/414782a 1:CAS:528:DC%2BD38Xhtlymtg%3D%3D 11742409 (Pubitemid 34000780)