(4-氟-苯基)-(1H-咪唑-2-基甲基)-胺 | 166096-17-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (4-氟-苯基)-(1H-咪唑-2-基甲基)-胺
• 英文名称: (4-fluoro-phenyl)-(1H-imidazol-2-ylmethyl)-amine
• 英文别名: 4-fluoro-N-(1H-imidazol-2-ylmethyl)aniline
• CAS: 166096-17-9
• 化学式: C₁₀H₁₀FN₃
• 分子量: 191.208
• InChiKey: GYNYGOFCVPTFRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  40.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-6-nitro-2-methyl-2-dimethoxymethyl-3,4-epoxy-3,4-dihydro-2H-1-benzopyran 、 (4-氟-苯基)-(1H-咪唑-2-基甲基)-胺 生成 (2S,3S,4R)-6-nitro-4-[N-(4-fluorophenyl)-N-(1H-imidazol-2-ylmethyl)amino]-3-hydroxy-2-methyl-2-dimethoxymethyl-3,4-dihydro-2H-1-benzopyran
  参考文献：
  名称：

  Benzopyran derivatives substituted with secondary amines including imidazole, their preparation and pharmaceutical compositions containing them

  摘要：

  本发明涉及用次生胺包括咪唑取代的苯并吡喃衍生物、它们的制备以及包含它们的药物组合物。本发明在药理学上对于通过抗血管生成的性质治疗癌症、类风湿性关节炎和糖尿病视网膜病变非常有用，同时在保护心脏和神经细胞免受缺血再灌注损伤或保护器官方面也具有药理学上的用途。

  公开号：

  US20050267188A1
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (4-氟-苯基)-(1H-咪唑-2-基甲基)-胺
  参考文献：
  名称：

  Cardioselective Antiischemic ATP-Sensitive Potassium Channel (K_ATP) Openers. 5. Identification of 4-(N-Aryl)-Substituted Benzopyran Derivatives with High Selectivity

  摘要：

  This paper describes our studies aimed at the discovery of structurally distinct analogs of the cardioprotective K-ATP Opener BMS-180448 (2) with improved selectivity for the ischemic myocardium. The starting compound 6, derived from the indole analog 4, showed good cardioprotective potency and excellent selectivity compared to 2 and the first-generation K-ATP opener cromakalim (1). The structure-activity studies indicate that increasing the size of the alkyl ester leads to diminished potency as does its replacement with a variety of other groups (nitrile, methyl sulfone). Replacement of the ethyl ester of 6 with an imidazole gave the best compound 3 (BMS-191095) of this series which maintains the potency and selectivity of its predecessor 6. The results described in this publication further support that there is no correlation between vasorelaxant and cardioprotective potencies of K-ATP openers. Compound 3 is over 20- and 4000-fold more selective far the ischemic myocardium than 2 and cromakalim (1), respectively. The selectivity for the ischemic myocardium is achieved by reduction of vasorelaxant potency rather than enhancement in antiischemic potency. As for cromakalim (1) and 2, the cardioprotective effects of compound 3 are inhibited by cotreatment with the K-ATP blocker glyburide, indicating that the K-ATP Opening is involved in its mechanism of cardioprotection With its good oral bioavailability (47%) and plasma elimination half life (3 h) in rats, compound 3 offers an excellent candidate to investigate the role of residual vasorelaxant potency of 2 toward its cardioprotective activity in vivo.

  DOI：

  10.1021/jm9605905

文献信息

• AMINOMETHYL-2-IMIDAZOLES
  申请人：Galley Guido

  公开号：US20080096906A1

  公开（公告）日：2008-04-24

  The present invention relates to compounds of formula I wherein R 1 is selected from the group consisting of hydrogen or lower alkyl; R 2 is hydrogen, lower alkyl, lower alkenyl, lower alkyl substituted by hydroxy, lower alkyl substituted by halogen, —(CH 2 ) x —S-lower alkyl, —(CH 2 ) x —O-lower alkyl, —(CH 2 ) x —NHC(O)O-lower alkyl, —(CH 2 ) x -aryl, and —(CH 2 ) x -heteroaryl; each R 3 is selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, halogen, hydroxy, lower alkyl substituted by halogen, —O—(CH 2 ) m -aryl, —O—(CH 2 ) m -heteroaryl, —(CR 2 ) m -aryl, and —(CR 2 ) m -heteroaryl; each R is selected from the group consisting of hydrogen, lower alkyl and hydroxy; Ar is selected from the group consisting of phenyl, pyrimidin-2-yl, pyrimidin-4-yl and pyridin-3-yl; n is 0, 1 or 2; x is 0, 1, 2 or 3; m is 0 or 1; and to their pharmaceutically active salts.

  本发明涉及以下式I的化合物 其中 R1选择自羟基或较低烷基; R2为氢、较低烷基、较低烯基、被羟基取代的较低烷基、被卤素取代的较低烷基、—(CH2)x—S-较低烷基、—(CH2)x—O-较低烷基、—(CH2)x—NHC(O)O-较低烷基、—(CH2)x-芳基和—(CH2)x-杂环基中的一种; 每个R3选择自氢、较低烷基、较低烷氧基、卤素、羟基、被卤素取代的较低烷基、—O—(CH2)m-芳基、—O—(CH2)m-杂环基、—(CR2)m-芳基和—(CR2)m-杂环基中的一种; 每个R选择自氢、较低烷基和羟基; Ar选择自苯基、嘧啶-2-基、嘧啶-4-基和吡啶-3-基; n为0、1或2; x为0、1、2或3; m为0或1; 以及其药用活性盐。
• [EN] BENZOPYRAN DERIVATIVES SUBSTITUTED WITH SECONDARY AMINES INCLUDING IMIDAZOLE, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] DERIVES DE BENZOPYRANE SUBSTITUES PAR DES AMINES SECONDAIRES DONT IMIDAZOLE, PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：KOREA RES INST CHEM TECH

  公开号：WO2004014898A1

  公开（公告）日：2004-02-19

  The present invention relates to benzopyran derivatives substituted with secondary amines including imidazole, their preparation, and pharmaceutical compositions containing them. The present invention is pharmacologically useful for the treatment of cancer, rheumatoid arthritis, and diabetic retinopathies through anti-angiogenic properties, and also pharmacologically useful in the protection of heart and neuronal cells against ischemia-reperfusion injury or preserving organs.

  本发明涉及取代了次级胺（包括咪唑）的苯并吡喃衍生物，以及其制备方法和含有它们的药物组合物。本发明在药理学上可用于治疗癌症、类风湿性关节炎和糖尿病视网膜病变，通过抗血管生成的特性，同时在保护心脏和神经细胞免受缺血再灌注损伤或保存器官方面也具有药理学上的用途。
• 4-Arylamino-benzopyran and related compounds
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0648758A1

  公开（公告）日：1995-04-19

  Compounds having the formula and pharmaceutically acceptable salts thereof wherein X is alkyl, Y is a single bond, -CH₂-, -C(O)-, -O-, -S- or -N(R⁸)- where R⁸ is hydrogen, alkyl, haloalkyl, aryl, arylalkyl, cycloalkyl or (cycloalkyl)alkyl, and R¹ to R⁷ are as defined herein. These compounds have potassium channel activating activity and are useful, therefore for example, as cardiovascular agents.

  具有以下化学式和药学上可接受的盐的化合物，其中X为烷基，Y为单键，-CH₂-，-C（O）-，-O-，-S-或-N（R⁸）-，其中R⁸为氢，烷基，卤代烷基，芳基，芳基烷基，环烷基或（环烷基）烷基，而R¹到R⁷如本文所定义。这些化合物具有钾通道激活活性，因此可用作心血管药物等用途。
• PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING MACULAR DEGENERATION
  申请人：Yi Kyu-Yang

  公开号：US20140018402A1

  公开（公告）日：2014-01-16

  The present invention provides a pharmaceutical composition for preventing or treating macular degeneration, which comprises benzopyran derivatives substituted with secondary amines including imidazole or pharmaceutically acceptable salts thereof as an active ingredient. The pharmaceutical composition of the present invention may be used in the form of eye drops.

  本发明提供了一种用于预防或治疗黄斑退化的药物组合物，其包括以含有咪唑等次生胺的苯并吡喃衍生物或其药学上可接受的盐为活性成分。本发明的药物组合物可以以眼药水的形式使用。
• Pharmaceutical composition for preventing or treating macular degeneration
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY

  公开号：US10485786B2

  公开（公告）日：2019-11-26

  The present invention provides a pharmaceutical composition for preventing or treating macular degeneration, which comprises benzopyran derivatives substituted with secondary amines including imidazole or pharmaceutically acceptable salts thereof as an active ingredient. The pharmaceutical composition of the present invention may be used in the form of eye drops.

  本发明提供了一种用于预防或治疗黄斑变性的药物组合物，其活性成分包括被包括咪唑在内的仲胺取代的苯并吡喃衍生物或其药学上可接受的盐类。本发明的药物组合物可以滴眼液的形式使用。