An efficient and straight forward synthesis of (5S)-1-benzyl-5- (1H-imidazol-1-ylmethyl)-2-pyrrolidinone (MM1): a novel antihypertensive agent

Springer Science and Business Media LLC - Tập 21 Số 3 - Trang 321-324 - 2012
J. S. Prasad1, Manoher Bhushan Pathak1, Sharad Kumar Panday1
1Department of Chemistry, Faculty of Engineering and Technology, M. J. P. Rohilkhand University, Bareilly, UP, India

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Tài liệu tham khảo

Abston WT (1994) Non-peptide angiotensin II receptor antagonists. Expert Opin Invest Drugs 3:1105–1142

Altman J, Ben-Ishai D (1993) Synthesis of chiral 1,2,4-triaminobutanes. Tetrahedron: Asymmetry 4:91–100

Burnier M, Brunner HR (1999) Comparative antihypertensive effects of angiotensin II receptor antagonists. J Am Soc Nephrol 10(Suppl 12):S278–S282

But TYS, Toy PH (2006) Organocatalytic Mitsunobu reaction. J Am Chem Soc 128:9636–9637 (and references cited therein)

Carini DJ, Dunica JV, Johnson AL, Chiu AT, Price WA, Wong PC, Timmermans PBMWM (1990) Non-peptide angiotensin II receptor antagonists: N-[(benzyloxy) benzyl] imidazole and related compounds as potent antihypertensives. J Med Chem 33:1330–1336

Corvol P (1989) New therapeutic prospects of renin angiotensin system inhibition. Clin Exp Hypertens A 11(Suppl.2):463–470

De Casparo M, Catt KJ, Inagami T, Wright JW, Unger T (2000) The angiotensin II receptor antagonists. Pharmacol Rev 52:415–472

Duncia JV, Chiu AT, Carini DJ, Gregory GB, Johnson AL, Price WA, Wells GJ, Wong PC, Calabrese JC, Timmermans PBMWM (1990) The discovery of potent nonpeptide angiotensin II receptor antagonists: a new class of potent antihypertensives. J Med Chem 33:1312–1329

Easthope SE, Jarvis B (2002) Candesartan cilexetil: an update of its use in essential hypertension. Drugs 62(8):1253–1287

Gavras H, Brunner HR, Turini GA, Kershaw GR, Tifft CP, Cuttelod S, Gevras I, Vukovich RA, McKinstry DNN (1978) Antihypertensive effects of the oral angiotensin converting enzyme inhibitor SQ 14225 in man. New Eng J Med 298(18):991–995

Hughes DL (1992) The Mitsunobu reaction. Org React 42:335–656

Kim EJ, KO SY, Dziadulewicz EK (2005) Mitsunobu alkylation of imidazole: a convenient route to chiral ionic liquids. Tetrahedron Lett 46(4):631–633

Laragh JH (1980) In: Case DB (ed) Captopril and hypertension. Plenum, New York, p 173

Lepore SD, He Y (2003) Use of sonication for the coupling of sterically hindered substrates in the phenolic Mitsunobu reaction. J Org Chem 68:8261–8263

Matsoukas JM, Hondrelis J, Keramida M, Mavromoustakos T, Makriyannis A, Yamdagni R, Wu Q, Moore GJ (1994) Role of the NH2-terminal domain of angiotensin II (ANG II) and [Sar1]angiotensin II on conformation and activity. NMR evidence for aromatic ring clustering and peptide backbone folding compared with [des-1, 2, 3]angiotensin II. J Biol Chem 269:5303–5312

Mavromoustakos T, Zervou M, Zoumpoulakis P, Kyrikou I, Benetis NP, Polevaya L, Roumelioti P, Giatas N, Zoga A, Minakakis PM, Kolocouris A, Vlahakos D, Golic GS, Matsoukas J (2004) Conformation and bioactivity. Design and discovery of novel antihypertensive drugs. Curr Top Med Chem 4:385–401

Mavromoustakos T, Minakakis PM, Kokotos CG, Kontogianni P, Politi A, Zoumpoulakis P, Findlay J, Cox A, Balmforth A, Zoga A, Iliodromitis E (2006) Synthesis, binding studies, and in vivo biological evaluation of novel non-peptide antihypertensive analogues. Bioorg Med Chem 14:4353–4360

Millard MP, Rossat J, Beunner HR, Burnier M (2000) Tasosartan, Enoltasosartan, and angiotensin II receptor blockade: the confounding role of protein binding. J Pharmacol Exp Ther 295(2):649–654

Moutevelis-Minakakis P, Gianni M, Stougiannou H, Zoumpoulakis P, Zoga A, Vlahakos D, Iliodromitis E, Mavromoustakos T (2003) Design and synthesis of novel antihypertensive drugs. Bioorg Med Chem Lett 13:1737–1740

Olofsson B, Wijtmans R, Somfai P (2002) Synthesis of N–H vinylaziridines: a comparative study. Tetrahedron 58:5979–5982

Panday SK, Prasad J, Dikshit DK (2009) Pyroglutamic acid: a unique chiral synthon. Tetrahedron: Asymmetry 20:1581–1632 (and references cited therein)

Peterson JS, Fels G, Rapoport H (1984) Chirospecific synthesis of (+) and (−)-anatoxin a. J Am Chem Soc 106:4539–4547

Polevaya L, Mavromoustakos T, Zoumboulakis P, Golic GS, Roumelioti P, Giatas N, Mutule I, Keivish T, Vlahakos DV, Iliodromitis EK, Kremastinos DT, Matsoukas J (2001) Synthesis and study of a cyclic angiotensin II antagonist analogue reveals the role of pi*–pi* interactions in the C-terminal aromatic residue for agonist activity and its structure resemblance with AT(1) non-peptide antagonists. Bioorg Med Chem 9:1639–1647

Rippin J, Bain SC, Barbett AH (2002) Rationale and design of diabetics exposed to telmisartan and enalapril (DETAIL) study. J Diabet Complicat 16(3):195–200

Roumelioti P, Polevaya L, Zoumpoulakis P, Giatas N, Mutule I, Keivish T, Zoga A, Vlahakos D, Iliodromitis E, Kremastinos D, Grdadolnik SG, Mavromoustakos T, Matsoukas J (2002) Design, synthesis and biological evaluation of cyclic angiotensin II analogues with 3, 5 side-chain bridges. Role of C-terminal aromatic residue and ring cluster for activity and implications in the drug design of AT1 non-peptide antagonists. Bioorg Med Chem Lett 12:2627–2633

Sen SE, Roach SL (1995) A convenient two step procedure for the synthesis of allylic amines from allylic alcohols. Synthesis 756–758