CAS: 871362-31-1; 2-Chloro-4-((2,5-Dimethyl-1-(4-(Trifluoromethoxy)Phenyl)-1H-Imidazol-4-yl)Ethynyl)Pyridine

该化合物是一个合成有机化合物,其结构复杂,包括一个环,一个非碘杂物和三氟乙氧组.该化合物通常具有中溶性等特性,并具有潜在的生物活动,因此对药物研究感兴趣.氯和三氟甲基基亚化合物的存在可影响其电子特性和再活动,有可能加强其与生物目标的相互作用.该化合物还可能显示具体的药理学活动,经常在药物开发过程中对此进行调查.其合成涉及多步骤的有机反应,并且由于存在可能对环境和健康造成风险的卤化组,因此必须小心处理.

结构式图片

物理性质

MSDS等安全信息

合成工艺路线路线简述

    📜3-Chloro-2-(2-Chloropyridin-4-yl)-3-[2,5-Dimethyl-1-(4-Trifluoromethoxyphenyl)-1H-Imidazol-4-Yl]Propenal置于potassium Tert-Butylate体系中,用 四氢呋喃,水 作为反应溶剂,化学反应 1.0H,以27%的收率获得产物mglu5受体变构拮抗剂ctep
    参考文献:Metabotropic Glutamate Receptor 5 Negative Allosteric Modulators: Discovery Of 2-Chloro-4-[1-(4-Fluorophenyl)-2,5-Dimethyl-1H-Imidazol-4-Ylethynyl]Pyridine (Basimglurant,Ro4917523),A Promising Novel Medicine For Psychiatric Diseases
    标题:Metabotropic Glutamate Receptor 5 Negative Allosteric Modulators: Discovery Of 2-Chloro-4-[1-(4-Fluorophenyl)-2,5-Dimethyl-1H-Imidazol-4-Ylethynyl]Pyridine (Basimglurant,Ro4917523),A Promising Novel Medicine For Psychiatric Diseases
    摘要:Negative Allosteric Modulators (Nams) Of Metabotropic Glutamate Receptor 5 (Mglu5) Have Potential For The Treatment Of Psychiatric Diseases Including Depression,Fragile X Syndrome (Fxs),Anxiety,Obsessive-Compulsive Disorders,And Levodopa Induced Dyskinesia In Parkinson'S Disease. Herein We Report The Optimization Of A Weakly Active Screening Hit 1 To The Potent And Selective Compounds Chloro-4-[1-(4-Fluorophenyl)-2,5-Dimethyl-1H-Imidazol-4-Ylethynyl]Pyridine (Basimglurant,2) And 2-Chloro-4-((2,5-Dimethyl-1-(4-(Trifluoromethoxy)Phenyl)-1H-Imidazol-4-yl)Ethynyl)Pyridine (Ctep,3). Compound 2 Is Active In A Broad Range Of Anxiety Tests Reaching The Same Efficacy But At A 10-To 100-Fold Lower Dose Compared To Diazepam And Is Characterized By Favorable Dmpk Properties In Rat And Monkey As Well As An Excellent Preclinical Safety Profile And Is Currently In Phase Ii Clinical Studies For The Treatment Of Depression And Fragile X Syndrome. Analogue 3 Is The First Reported Mglu5 Nam With A Long Half-Life In Rodents And Is Therefore An Ideal Tool Compound For Chronic Studies In Mice And Rats.
    DOI:10.1021/jm501642C

    海关参考信息

    专利信息


    专利号:KR-20160017105-A
    优先权日:2008-01-15
    标题:Synthesis of resorcylic acid lactones useful as therapeutic agents

    专利号:CA-1116175-A
    优先权日:1976-02-20
    标 题 :Bicyclic lactone derivatives employed as intermediates in the synthesis of prostaglandines and process for the preparation of same

    专利号:KR-20110003468-A
    优先权日:2008-01-15
    标题:Synthesis of resorcylic acid lactones useful as therapeutic agents

    专利号:MX-2010007755-A
    优先权日:2008-01-15
    标 题 :SYNTHESIS OF RESORCILIC ACID LACTONS USEFUL AS THERAPEUTIC AGENTS.

    专利号:RU-2534527-C2
    优先权日:2008-01-15
    标题 :Synthesis of resorcylic acid lactones used as therapeutic agents

    专利号:WO-2009091921-A1
    优先权日:2008-01-15
    标题:Synthesis of resorcylic acid lactones useful as therapeutic agents

    其他信息查阅

    供应商参考报价(招募中)

    品牌试剂参考报价(招募中)

    实用工具

    ⚠️全国化工行业净网倡议书
    📋制造商识别码
    📖 海关编码查询
    📝MSDS生成器

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Tian D, Stoppel LJ, Heynen AJ, Lindemann L, Jaeschke G, Mills AA, Bear MF. Contribution of mGluR5 to pathophysiology in a mouse model of human chromosome 16p11.2 microdeletion. Nat Neurosci. 2015 Feb;18(2):182-4. doi: 10.1038/nn.3911. Epub 2015 Jan 12.
    2: Jaeschke G, Kolczewski S, Spooren W, Vieira E, Bitter-Stoll N, Boissin P, Borroni E, Büttelmann B, Ceccarelli S, Clemann N, David B, Funk C, Guba W, Harrison A, Hartung T, Honer M, Huwyler J, Kuratli M, Niederhauser U, Pähler A, Peters JU, Petersen A, Prinssen E, Ricci A, Rueher D, Rueher M, Schneider M, Spurr P, Stoll T, Tännler D, Wichmann J, Porter RH, Wettstein JG, Lindemann L. Metabotropic glutamate receptor 5 negative allosteric modulators: discovery of 2-chloro-4-[1-(4-fluorophenyl)-2,5-dimethyl-1H-imidazol-4-ylethynyl]pyridine (basimglurant, RO4917523), a promising novel medicine for psychiatric diseases. J Med Chem. 2015 Feb 12;58(3):1358-71. doi: 10.1021/jm501642c. Epub 2015 Feb 2. doi: 10.1038/npp.2014.308.
    4: Michalon A, Bruns A, Risterucci C, Honer M, Ballard TM, Ozmen L, Jaeschke G, Wettstein JG, von Kienlin M, Künnecke B, Lindemann L. Chronic metabotropic glutamate receptor 5 inhibition corrects local alterations of brain activity and improves cognitive performance in fragile X mice. Biol Psychiatry. 2014 Feb 1;75(3):189-97. doi: 10.1016/j.biopsych.2013.05.038. Epub 2013 Jul 30. doi: 10.1016/j.neuron.2012.03.009. doi: 10.1016/j.neuron.2012.03.014. doi: 10.1124/jpet.111.185660. Epub 2011 Aug 17.

    合成参考文献


    参考文献:10.1007/978-3-030-87480-3_3
    摘要:Réus GZ, Abelaira HM, Coutellier LD, Manosso LM, Pavlovic ZM. Role of Glutamatergic Neurotransmission in the Pathophysiology of Stress-Related Disorders and Chronic Stress Response. 2022. In: Glutamate and Neuropsychiatric Disorders.
    参考文献:10.1124/mol.119.115964
    摘要:Lee TD, Lee OW, Brimacombe KR, Chen L, Guha R, Lusvarghi S, Tebase BG, Klumpp-Thomas C, Robey RW, Ambudkar SV, Shen M, Gottesman MM, Hall MD. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular Pharmacology. 2019 Nov;96(5):629–40. doi: 10.1124/mol.119.115964.
    📝 需求与反馈
    尽可能描述清楚需求与问题信息
    ×

    通知