N-(1H-咪唑-2-基甲基)苯胺 | 166096-14-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(1H-咪唑-2-基甲基)苯胺
• 英文名称: N-((1H-imidazol-2-yl)methyl)benzenamine
• 英文别名: N-[(1H-Imidazol-2-yl)methyl]-N-phenylamine；(1H-imidazol-2-ylmethyl)-phenyl-amine；N-(1H-imidazol-2-ylmethyl)aniline
• CAS: 166096-14-6
• 化学式: C₁₀H₁₁N₃
• mdl: MFCD08668368
• 分子量: 173.217
• InChiKey: LKTOVFRMNAMQMZ-UHFFFAOYSA-N

物化性质

• 熔点：
  195.0-197.2 °C
• 沸点：
  449.9±28.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 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：
  2

反应信息

• 作为反应物：
  描述：

  N-(1H-咪唑-2-基甲基)苯胺 在 盐酸 、 水 、 三乙酰氧基硼氢化钠 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 19.0h， 生成 (1H-Imidazol-2-ylmethyl)-isopropyl-phenyl-amine
  参考文献：
  名称：

  Optimisation of imidazole compounds as selective TAAR1 agonists: Discovery of RO5073012

  摘要：

  A series of imidazole compounds has been identified which affords potent and selective partial and full agonists of the TAAR1 receptor. Starting from 2-benzyl-imidazoline screening hits, a series of structurally related 2-benzyl- and 4-benzyl-imidazoles was investigated first, but it proved highly challenging to obtain compounds having sufficient selectivity against the adrenergic alpha 2 receptor. This issue could be successfully addressed by modification of the linker region and SAR exploration led to the discovery of highly selective isopropyl-substituted 4-aminomethyl-imidazole compounds. The work culminated in the identification of the selective TAAR1 partial agonist RO5073012 (4-chlorophenyl)-(1H-imidazol-4-ylmethyl)-isopropyl-amine, 24), which has a good pharmacokinetic profile after oral administration in rodents. RO5073012 has been found to be active in a behavioural rat model which is considered indicative for schizophrenia. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.060
• 作为产物：
  描述：

  N-((1H-imidazol-2-yl)methylene)aniline 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 N-(1H-咪唑-2-基甲基)苯胺
  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

• 1,2,3-Triazole-boranes: stable and efficient reagents for ketone and aldehyde reductive amination in organic solvents or in water
  作者：Wenyan Liao、Yunfeng Chen、Yuxiu Liu、Haifeng Duan、Jeffrey L. Petersen、Xiaodong Shi

  DOI：10.1039/b915361f

  日期：——

  Air, moisture and thermally stable 1,2,3-triazole-borane complexes were developed as new practical reagents for ketone/aldehyde amination with high efficiency and excellent substrate diversity.

  空气，水分和热稳定的1,2,3-三唑-硼烷配合物被开发为高效/高效的酮/醛胺化的新型实用试剂，并且具有出色的底物多样性。
• 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。
• 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。
• Dérivés de 4-phénylaminométhylimidazole, procédé de préparation, antagonistes des récepteurs angiotensin II et leur application en thérapeutique
  申请人：FOURNIER INDUSTRIE ET SANTE

  公开号：EP0564356A1

  公开（公告）日：1993-10-06

  La présente invention concerne les phényl-amino-méthyl-imidazoles de formule: (où les groupes R₁ à R₇ sont définis comme indiqué dans la description). Elle concerne également leur procédé de préparation et leur application en thérapeutique en tant qu'agents antagonistes de l'angiotensine II, utiles dans le traitement de l'hypertension, des désordres circulatoires et du glaucome.

  本发明涉及式中的苯基-氨基-甲基-咪唑： (其中基团 R₁至 R₇ 的定义如描述中所示）。 本发明还涉及其制备工艺及其作为血管紧张素 II 拮抗剂在治疗高血压、循环系统疾病和青光眼方面的应用。
• Substituted pharmacologically acitve imidazole derivatives and their preparation and use
  申请人：Farmos Group Ltd.

  公开号：EP0081324B1

  公开（公告）日：1986-08-06