2-(2-甲基-1H-苯并咪唑-1-基)乙醇 | 4946-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-(2-甲基-1H-苯并咪唑-1-基)乙醇
• 中文别名: 2-甲基-(9ci)-1H-苯并咪唑-1-乙醇
• 英文名称: 2-(2-methyl-1H-benzo[d]imidazol-1-yl)-ethanol
• 英文别名: 2-(2-methyl-1H-benzo[d]imidazol-1-yl)ethanol；2-(2-methyl-benzoimidazol-1-yl)-ethanol；2-(2-methyl-benzimidazol-1-yl)-ethanol；2-(2-Methyl-benzimidazol-1-yl)-aethanol；2-(2-methyl-1H-benzoimidazol-1-yl)ethanol；2-Methylbenzimidazol-1-ylethanol；2-(2-methylbenzimidazol-1-yl)ethanol
• CAS: 4946-08-1
• 化学式: C₁₀H₁₂N₂O
• mdl: MFCD00022844
• 分子量: 176.218
• InChiKey: CURPBJGJXFWNMF-UHFFFAOYSA-N

物化性质

• 沸点：
  374.9±25.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(2-甲基-1H-苯并咪唑-1-基)乙醇 在 palladium on activated charcoal 氯化亚砜 、 N-羟基-7-氮杂苯并三氮唑 、 氢气 、 caesium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 118.08h， 生成 5-phenyl-oxazole-4-carboxylic acid {1-[2-(2-methyl-benzoimidazol-1-yl)-ethyl]-1H-pyrazol-4-yl}-amide
  参考文献：
  名称：

  [EN] NOVEL PYRAZOLE AND IMIDAZOLE DERIVATIVES USEFUL AS OREXIN ANTAGONISTS
  [FR] NOUVEAUX DÉRIVÉS DE PYRAZOLE ET D'IMIDAZOLE UTILES À TITRE D'ANTAGONISTES D'OREXINE

  摘要：

  本发明涉及式(I)的吡唑和咪唑衍生物，其中U、V、L、X、Y、R1、(R2)n和(R3)m以及环A如描述中所述，其制备方法，其药学上可接受的盐，以及作为药物的用途，含有一个或多个式(I)化合物的药物组合物，特别是作为促进睡眠的药物受体拮抗剂的用途。

  公开号：

  WO2012110986A1
• 作为产物：
  描述：

  2-(2-甲基苯并咪唑-1-基)乙酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到2-(2-甲基-1H-苯并咪唑-1-基)乙醇
  参考文献：
  名称：

  Discovery of Novel KRAS-PDEδ Inhibitors by Fragment-Based Drug Design

  摘要：

  [Graphics]Targeting KRAS-PDE delta protein-protein interactions with small molecules represents a promising opportunity for developing novel antitumor agents. However, current KRAS-PDE delta inhibitors are limited by poor cellular antitumor potency and the druggability of the target remains to be validated by new inhibitors. To tackle these challenges, herein, novel, highly potent KRAS-PDE delta inhibitors were identified by fragment-based drug design, providing promising lead compounds or chemical probes for investigating the biological functions and druggability of KRAS-PDE delta interaction.

  DOI：

  10.1021/acs.jmedchem.8b00057

文献信息

• Structure Guided Design and Kinetic Analysis of Highly Potent Benzimidazole Inhibitors Targeting the PDEδ Prenyl Binding Site
  作者：Gunther Zimmermann、Carsten Schultz-Fademrecht、Philipp Küchler、Sandip Murarka、Shehab Ismail、Gemma Triola、Peter Nussbaumer、Alfred Wittinghofer、Herbert Waldmann

  DOI：10.1021/jm500632s

  日期：2014.6.26

  organization of K-Ras is controlled by the prenyl binding protein PDEδ, which enhances Ras diffusion in the cytosol. Inhibition of the Ras–PDEδ interaction by small molecules impairs Ras localization and signaling. Here we describe in detail the identification and structure guided development of Ras–PDEδ inhibitors targeting the farnesyl binding pocket of PDEδ with nanomolar affinity. We report kinetic

  K-Ras是最常见的信号转导人类致癌基因之一。Ras信号传导活性需要GTPase的正确细胞定位。K-Ras的空间组织受到异戊二烯结合蛋白PDEδ的控制，异戊二烯结合蛋白PDEδ增强Ras在细胞质中的扩散。小分子抑制Ras–PDEδ相互作用会削弱Ras的定位和信号传导。在这里，我们详细描述了靶向Ras–PDEδ抑制剂的鉴定和结构指导的开发，该抑制剂靶向具有纳摩尔摩尔亲和力的PDEδ的法呢基结合袋。我们报道了表征最有效的小分子配体与PDEδ结合的动力学数据，并证明了它们与细胞裂解液中的内源PDEδ结合。
• Copper-catalyzed benzylic C(sp³)–H alkoxylation of heterocyclic compounds
  作者：Noriaki Takemura、Yoichiro Kuninobu、Motomu Kanai

  DOI：10.1039/c4ob00215f

  日期：——

  We achieved intra- and intermolecular C(sp3)–H alkoxylation of benzylic positions of heteroaromatic compounds using CuBrn (n = 1, 2)/5,6-dimethylphenanthroline (or 4,7-dimethoxyphenanthroline) and (tBuO)2 as a catalyst and an oxidant, respectively. The reaction proceeded at both terminal and internal benzylic positions of the alkyl groups. The intramolecular alkoxylation was performed on a gram scale

  我们使用CuBr n（n = 1，2）/ 5,6-二甲基菲咯啉（或4,7-二甲氧基菲咯啉）和（t BuO）2实现了杂芳族化合物苄基位置的分子内和分子间C（sp 3）-H烷氧基化分别作为催化剂和氧化剂。反应在烷基的末端和内部苄基位置上进行。分子内烷氧基化以克为单位进行。
• Dihydropyridine anti-allergic and anti-inflammatory agents
  申请人：Pfizer Inc.

  公开号：US04801598A1

  公开（公告）日：1989-01-31

  Compounds of the formula: ##STR1## where R is 2-substituted phenyl said substituent being chloro, bromo, cyano, methyl, methylthio, methylsulfonyl, trifluoromethyl, hydroxy, methoxy or benzyloxy; R.sup.1 is hydrogen, lower alkyl, pyridyl, thiazolyl, isoxazolyl, thiadiazdyl or thiazdylmethyl; R.sup.2 is hydrogen or lower alkyl; R.sup.3 is hydroxy, lower alkoxy, benzyloxy, amino, lower alkylamino or morpholino; Y is alkylene having two to six carbon atoms; and X is benzimidazolyl optionally substituted by lower alkyl, chloro or trifluoromethyl.

  式为：##STR1##其中R是2-取代苯基，该取代基是氯、溴、氰基、甲基、硫甲基、磺酰甲基、三氟甲基、羟基、甲氧基或苄氧基；R.sup.1是氢、低碳烷基、吡啶基、噻唑基、异噁唑基、噻二唑基或噻二唑甲基；R.sup.2是氢或低碳烷基；R.sup.3是羟基、低碳氧基、苄氧基、氨基、低碳烷基氨基或吗啉基；Y是具有2至6个碳原子的烷基；X是苯并咪唑基，可选择地被低碳烷基、氯或三氟甲基取代。
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• NOVEL PYRAZOLE AND IMIDAZOLE DERIVATIVES USEFUL AS OREXIN ANTAGONISTS
  申请人：Bolli Martin

  公开号：US20130324579A1

  公开（公告）日：2013-12-05

  The present invention relates to pyrazole and imidazole derivatives of formula (I) wherein U, V, L, X, Y, R 1 , (R 2 ) n and (R 3 ) m and ring A are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as orexin receptor antagonists.

  本发明涉及公式（I）的吡唑和咪唑衍生物，其中U、V、L、X、Y、R1、（R2）n和（R3）m以及环A如说明书所述，其制备方法，其制备的药物学上可接受的盐以及它们作为药物的用途，包括含有一个或多个公式（I）化合物的制药组合物，特别是它们作为促进睡眠药物的用途。