Design, synthesis, and docking studies of novel telmisartan-glitazone hybrid analogs for the treatment of metabolic syndrome

Medicinal Chemistry Research

Volumn 18, Issue 7, 2009, Pages 589-610

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

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

AT1 antagonist; Glitazones; Hypertension; Metabolic syndrome; PPAR gamma; Telmisartan; Type 2 diabetes

Indexed keywords

ANGIOTENSIN 1 RECEPTOR; ANGIOTENSIN II ANTAGONIST; HTR 01; HTR 02; HTR 03; HTR 04; HTR 05; METHYL 2 [2 (5 CYCLOHEXYL N METHYLPENTANAMIDO)ETHOXY] 5 [(2,4 DIOXOTHIAZOLIDIN 5 YL)METHYL]BENZOATE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST; ROSIGLITAZONE; TELMISARTAN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIHYPERTENSIVE ACTIVITY; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG BINDING; DRUG DESIGN; DRUG MECHANISM; DRUG SYNTHESIS; METABOLIC SYNDROME X; MOLECULAR DOCKING; MOLECULAR MODEL; MOUSE; NONHUMAN; RAT;

EID: 70349243286     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-008-9152-x     Document Type: Article

References (18)

1. AJ Balmforth AJ Lee P Warburton D Donnelly SG Ball 1997 The conformational change responsible for AT1 receptor activation is dependent upon two Juxtaposed asparagine residues on transmembrane helixes III and VII J Biol Chem 272 4245 4251 10.1074/jbc.272.7.4245 9020140 10.1074/jbc.272.7.4245 1:CAS:528:DyaK2sXht1Oksbo%3D (Pubitemid 27078494)
2. SC Benson HA Pershadsingh CI Ho A Chittiboyina P Desai M Pravenec N Qi J Wang MA Avery TW Kurtz 2004 Identification of telmisartan as a unique angiotensin II receptor antagonist with selective PPARgamma-modulating activity Hypertension 43 993 1002 10.1161/01.HYP.0000123072.34629.57 15007034 10.1161/01.HYP.0000123072.34629.57 1:CAS:528:DC%2BD2cXjt1GmtrY%3D (Pubitemid 38579904)
3. 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 14744958 10.1161/01.CIR.0000111245.75752.C6 (Pubitemid 38133916)
4. Harrold M (2002) Foye's principles of medicinal chemistry, 5th edn. Lippincott Williams & Wilkins, Philadelphia, pp 533-561
5. 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 12021402 10.1124/mol.61.6.1404 1:CAS:528:DC%2BD38XksVWrtLo%3D (Pubitemid 34575751)
6. FH Messerli 2002 Vasodilatory edema: a common side effect of antihypertensive therapy Curr Cardiol Rep 4 479 482 10.1007/s11886-002-0110-9 12379167 10.1007/s11886-002-0110-9
7. National Institutes of Health, Treatment of Insulin Resistance in Hypertensive, Obese Adolescents. http://clinicaltrials.gov/show/NCT00185705. Accessed 6 January, 2009
8. Ohnota M, Orita K, Aizawa Y, Yoshida N, Sakamaki T (2001) Process for the preparation of thiazolidinedione derivatives. WO 2001096321
9. T Okubo F Tsuchiko T Wakasawa T Nambara 1988 Preparation and antigenic properties of 2-hydroxyestrone-[C-15]-bovine serum albumin conjugate Chem Pharm Bull (Tokyo) 36 3519 3514 1:CAS:528:DyaL1MXhsFCltLo%3D
10. 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)
11. HA Pershadsingh 2006 Treating the metabolic syndrome using angiotensin receptor antagonists that selectively modulate peroxisome proliferator-activated receptor-gamma Int J Biochem Cell Biol 38 766 781 10.1016/j.biocel.2005.08.006 16298156 10.1016/j.biocel.2005.08.006 1:CAS:528:DC%2BD28Xit1Ohtbc%3D (Pubitemid 43372054)
12. 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 8258826 10.1021/jm00077a007 1:CAS:528:DyaK2cXpsVOgsw%3D%3D (Pubitemid 24024676)
13. AM Rouhi 2004 Metabolic syndrome Chem Eng News 82 83 99
14. M Schupp J Janke R Clasen T Unger U Kintscher 2004 Angiotensin type 1 receptor blockers induce peroxisome proliferator-activated receptor-gamma activity Circulation 109 2054 2057 10.1161/01.CIR.0000127955.36250.65 15117841 10.1161/01.CIR.0000127955.36250.65 1:CAS:528:DC%2BD2cXjsVWqsrs%3D (Pubitemid 38620211)
15. 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 14556962 10.1016/S0167-0115(03)00172-1 1:CAS:528:DC%2BD3sXnvVKqs70%3D (Pubitemid 37211436)
16. RC Speth JW Harding 2001 Radiolabeling of angiotensin peptides Methods Mol Med 51 275 295 1:CAS:528:DC%2BD3cXot1Wru7c%3D
17. 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
18. E Vedejs JS Stults 1988 Synthesis of azocine derivatives from thio aldehyde Diels-Alder adducts J Org Chem 53 2226 2232 10.1021/jo00245a019 10.1021/jo00245a019 1:CAS:528:DyaL1cXitVCntbg%3D