5-(chloromethyl)-2-phenyl-1H-imidazole hydrochloride | 52353-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(chloromethyl)-2-phenyl-1H-imidazole hydrochloride
• 英文别名: 5-(chloromethyl)-2-phenyl-1H-imidazole;hydrochloride
• CAS: 52353-65-8
• 化学式: C₁₀H₉ClN₂*ClH
• 分子量: 229.109
• InChiKey: FUWSNBWNJGOFMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  28.7
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(chloromethyl)-2-phenyl-1H-imidazole hydrochloride 在 sodium cyanide 作用下， 以 二甲基亚砜 为溶剂， 生成 2-(2-phenyl-1H-imidazol-5-yl)acetonitrile
  参考文献：
  名称：

  [EN] MUTANT IDH1 INHIBITORS USEFUL FOR TREATING CANCER
  [FR] INHIBITEURS D'IDH1 MUTANTS UTILES POUR TRAITER LE CANCER

  摘要：

  公开号：

  WO2016106331A8
• 作为产物：
  描述：

  4-羟基甲基-2-苯基-1H-咪唑 在 氯化亚砜 作用下， 反应 2.17h， 以99%的产率得到5-(chloromethyl)-2-phenyl-1H-imidazole hydrochloride
  参考文献：
  名称：

  [EN] BICYCLIC HETEROARYL SUBSTITUTED COMPOUNDS
  [FR] COMPOSÉS BICYCLIQUES SUBSTITUÉS PAR HÉTÉROARYLE

  摘要：

  公开了公式(I)至(VIII)的化合物：(I) (II) (III) (IV) (V) (VI) (VII) (VIII)；或其立体异构体、互变异构体、药物可接受的盐、溶剂化物或前药，其中R3是与0至3个R3a取代的双环杂芳基团；且R1、R2、R3a、R4和n在此定义。还公开了使用这些化合物作为PAR4抑制剂的方法，以及包含这些化合物的药物组合物。这些化合物用于抑制或预防血小板聚集，用于治疗血栓栓塞障碍或作为血栓栓塞障碍的初级预防。

  公开号：

  WO2018013774A1

文献信息

• Mutant IDH1 inhibitors useful for treating cancer
  申请人：THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICE

  公开号：US10703746B2

  公开（公告）日：2020-07-07

  Compounds of Formula I and Formula II and the pharmaceutically acceptable salts thereof are disclosed The variables A, B, Y, Z, X1, X2, R1-4 and R13-18 are disclosed herein. The compounds are useful for treating cancer disorders, especially those involving mutant IDH1 enzymes. Pharmaceutical compositions containing compounds of Formula I or Formula II and methods of treatment comprising administering compounds of Formula I and Formula II are also disclosed.

  公开了式 I 和式 II 的化合物及其药学上可接受的盐 本文公开了变量 A、B、Y、Z、X1、X2、R1-4 和 R13-18。这些化合物可用于治疗癌症疾病，特别是涉及突变 IDH1 酶的疾病。还公开了含有式 I 或式 II 化合物的药物组合物以及包括施用式 I 和式 II 化合物的治疗方法。
• Discovery and Optimization of 2<i>H</i>-1λ²-Pyridin-2-one Inhibitors of Mutant Isocitrate Dehydrogenase 1 for the Treatment of Cancer
  作者：Jason M. Rohde、Surendra Karavadhi、Rajan Pragani、Li Liu、Yuhong Fang、Weihe Zhang、Andrew McIver、Hongchao Zheng、Qingyang Liu、Mindy I. Davis、Daniel J. Urban、Tobie D. Lee、Dorian M. Cheff、Melinda Hollingshead、Mark J. Henderson、Natalia J. Martinez、Kyle R. Brimacombe、Adam Yasgar、Wei Zhao、Carleen Klumpp-Thomas、Sam Michael、Joseph Covey、William J. Moore、Gordon M. Stott、Zhuyin Li、Anton Simeonov、Ajit Jadhav、Stephen Frye、Matthew D. Hall、Min Shen、Xiaodong Wang、Samarjit Patnaik、Matthew B. Boxer

  DOI：10.1021/acs.jmedchem.1c00019

  日期：2021.4.22
• 5-Substituted Imidazole-4-acetic Acid Analogues:  Synthesis, Modeling, and Pharmacological Characterization of a Series of Novel γ-Aminobutyric Acid_C Receptor Agonists
  作者：Christian Madsen、Anders A. Jensen、Tommy Liljefors、Uffe Kristiansen、Birgitte Nielsen、Camilla P. Hansen、Mogens Larsen、Bjarke Ebert、Benny Bang-Andersen、Povl Krogsgaard-Larsen、Bente Frølund

  DOI：10.1021/jm070447j

  日期：2007.8.1

  A series of ring-substituted analogues of imidazole-4-acetic acid (IAA, 4), a partial agonist at both GABA(A) and GABA(C) receptors (GABA = gamma-aminobutyric acid), have been synthesized. The synthesized compounds 8a-1 have been evaluated as ligands for the alpha(1)beta(2)gamma(2S) GABA(A) receptors and the rho(1) GABA(C) receptors using the FLIPR membrane potential (FMP) assay and by electrophysiology techniques. None of the tested compounds displayed activity at the GABA(A) receptors at concentrations up to 1000 mu M. However, the 5-Me, 5-Ph, 5-p-Me-Ph, and 5-p-F-Ph IAA analogues, 8a,c,f,g, displayed full agonist activities at the rho(1) receptors in the FMP assay (EC50 in the range 22-420 mu M). Ligand-protein docking identified the Thr129 in the alpha(1) subunit and the corresponding Ser168 residue in rho(1) as determinants of the selectivity displayed by the 5-substituted IAA analogues. The fact that GABA, 4, and 8a displayed decreased agonist potencies at a rho(1)Ser168Thr mutant compared to the WT rho(1) receptor strongly supported this hypothesis. However, in contrast to GABA and 4, which exhibited increased agonist potencies at a alpha(1)(Thr129Ser)beta(2)gamma(2) mutant compared to WT GABA(A) receptor, the data obtained for 8a at the WT and mutant receptors were nonconclusive.
• MUTANT IDH1 INHIBITORS USEFUL FOR TREATING CANCER
  申请人：The United States of America, as represented by The Secretary, Department of Health and Human Services

  公开号：EP3237385B1

  公开（公告）日：2021-11-24
• BICYCLIC HETEROARYL SUBSTITUTED COMPOUNDS
  申请人：Bristol-Myers Squibb Company

  公开号：EP3484878B1

  公开（公告）日：2020-08-19