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

被引:9
|
作者
Prasad, Jagdish [1 ]
Pathak, Manoher Bhushan [1 ]
Panday, Sharad Kumar [1 ]
机构
[1] MJP Rohilkhand Univ, Dept Chem, Fac Engn & Technol, Bareilly, Uttar Pradesh, India
关键词
Hypertension; Angiotensin-II; AT(1) antagonists; MM1; Mitsunobu reaction; N-benzyl-5(S)-pyroglutaminol; TERMINAL AROMATIC RESIDUE; II RECEPTOR ANTAGONISTS; BIOLOGICAL EVALUATION; ANGIOTENSIN; DESIGN; CONFORMATION; DISCOVERY;
D O I
10.1007/s00044-010-9536-6
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
(5S)-1-benzyl-5-(1H-imidazol-1-ylmethyl)-2-pyrrolidinone and its closely related analog was synthesized from (S)-pyroglutaminol and imidazole or substituted imidazole using Mitsunobu reaction as the key step.
引用
收藏
页码:321 / 324
页数:4
相关论文
共 50 条
  • [21] 6-(1-Benzyl-1H-pyrrol-2-yl)-2,4-dioxo-5-hexenoic Acids as Dual Inhibitors of Recombinant HIV-1 Integrase and Ribonuclease H, Synthesized by a Parallel Synthesis Approach
    Costi, Roberta
    Metifiot, Mathieu
    Esposito, Francesca
    Crucitti, Giuliana Cuzzucoli
    Pescatori, Luca
    Messore, Antonella
    Scipione, Luigi
    Tortorella, Silvano
    Zinzula, Luca
    Novellino, Ettore
    Pommier, Yves
    Tramontano, Enzo
    Marchand, Christophe
    Di Santo, Roberto
    JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (21) : 8588 - 8598
  • [22] Synthesis and anticonvulsant activity of novel imidazol"5(4H)"one and 5-oxo-4,5-dihydroimidazol-1-yl)propanamide derivatives
    Khalifa, Maha M. A.
    Baset, Marawan A.
    El-Eraky, Wafaa
    MEDICINAL CHEMISTRY RESEARCH, 2012, 21 (12) : 4447 - 4454
  • [23] Synthesis, crystal structure and biological evaluation of novel 2-(5-(hydroxymethyl)-3-phenyl-1H-pyrazol-1-yl)-1-phenylethanol derivatives
    Zheng, Liang-Wen
    Zhu, Jian
    Zhao, Bao-Xiang
    Huang, Yao-Hui
    Ding, Jun
    Miao, Jun-Ying
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (12) : 5792 - 5799
  • [24] Design, synthesis and biological evaluation of novel FXIa inhibitors with 2-phenyl-1H-imidazole-5-carboxamide moiety as P1 fragment
    Lei, Yu
    Zhang, Bing
    Zhang, Yan
    Dai, Xiwen
    Duan, Yulin
    Mao, Qing
    Gao, Jun
    Yang, Yuwei
    Bao, Ziyang
    Fu, Xuefeng
    Ping, Kunqi
    Yan, Chengda
    Mou, Yanhua
    Wang, Shaojie
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2021, 220
  • [25] Synthesis and Biological Evaluation of 5-benzyl-3-pyridyl-1H-1,2,4-triazole Derivatives as Xanthine Oxidase Inhibitors
    Li, Song-Ye
    Zhang, Ting-Jian
    Wu, Qing-Xia
    Olounfeh, Kamara M.
    Zhang, Yi
    Meng, Fan-Hao
    MEDICINAL CHEMISTRY, 2020, 16 (01) : 119 - 127
  • [26] 1-Benzyl-5-bromo-3-hydrazonoindolin-2-ones as Novel Anticancer Agents: Synthesis, Biological Evaluation and Molecular Modeling Insights
    Al-Warhi, Tarfah
    Almahli, Hadia
    Maklad, Raed M.
    Elsayed, Zainab M.
    El Hassab, Mahmoud A.
    Alotaibi, Ohoud J.
    Aljaeed, Nada
    Ayyad, Rezk R.
    Ghabour, Hazem A.
    Eldehna, Wagdy M.
    El-Ashrey, Mohamed K.
    MOLECULES, 2023, 28 (07):
  • [27] An Efficient Synthesis of New 5-(1-Aryl-1H-pyrazole-4-yl)-1H-tetrazoles from 1-Aryl-1H-pyrazole-4-carbonitriles via [3+2] Cycloaddition Reaction
    dos Santos, Mauricio S.
    Bernardino, Alice M. R.
    Pinheiro, Luiz C. S.
    Canto-Cavalheiro, Marilene M.
    Leon, Leonor L.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (06) : 1425 - 1428
  • [28] Synthesis and Biophysical Properties of Oligodeoxynucleotides Containing 2′-Deoxy-5-(4-nitro-1H-imidazol-1-yl)-β-D-uridine and 2′-Deoxy-5-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-β-D-uridine Monomers
    Gondela, Andrzej
    Kumar, Thatikonda Santhosh
    Walczak, Krzysztof
    Wengel, Jesper
    CHEMISTRY & BIODIVERSITY, 2010, 7 (02) : 350 - 362
  • [29] Synthesis and antiproliferative evaluation of novel 5-(4-methylpiperazin-1-yl)-2-phenyl-1H-benzimidazole derivatives
    Alp, Mehmet
    Gurkan-Alp, A. Selen
    Ozkan, Tulin
    Sunguroglu, Asuman
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES, 2015, 70 (3-4): : 79 - 85
  • [30] Synthesis and Rotational Isomerism of 1-Substituted Methyl (S)-[5-(2-Nitrophenyl)-1H-pyrazole-4-carbonyl]alaninates
    Senica, Luka
    Stopar, Karmen
    Friedrich, Miha
    Groselj, Uros
    Plavec, Janez
    Pockaj, Marta
    Podlipnik, Crtomir
    Stefane, Bogdan
    Svete, Jurij
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (01) : 146 - 161