[3-(4-溴苄基)-3H-咪唑-4-基]甲醇 | 220364-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [3-(4-溴苄基)-3H-咪唑-4-基]甲醇
• 中文别名: 1-(4-溴苄基)-5-羟甲基咪唑
• 英文名称: (1-(4-bromobenzyl)-1H-imidazol-5-yl)methanol
• 英文别名: 1-(4-Bromobenzyl)-5-hydroxymethyl-1H-imidazole；[3-(4-Bromo-benzyl)-3H-imidazol-4-YL]-methanol；[3-[(4-bromophenyl)methyl]imidazol-4-yl]methanol
• CAS: 220364-22-7
• 化学式: C₁₁H₁₁BrN₂O
• 分子量: 267.125
• InChiKey: JLBQCMBTWCNPRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  [3-(4-溴苄基)-3H-咪唑-4-基]甲醇 在 manganese(IV) oxide 、 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.0h， 生成 1-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)-1H-imidazole-5-carbaldehyde
  参考文献：
  名称：

  Triazole derivatives: A series of Darapladib analogues as orally active Lp-PLA2 inhibitors

  摘要：

  This Letter reports our efforts towards the optimization of our previously identified series of imidazole and triazole derivatives that lead to the discovery of a series of orally active Lp-PLA(2) inhibitors in C57 mice. These inhibitors are characterized by the presence of a diamine side chain in the molecules, such as 2c, 2f, and 4a. The introduction of the terminal-end amine succeeded in maintaining the in vitro activities at sub-nanomolar levels. The vivo activities could be greatly affected by variations in the two amines via modulating the metabolic stability and lipophilicity of the compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.062
• 作为产物：
  描述：

  1-[(4-溴苯基)甲基]-1,3-二氢-5-(羟基甲基)-2H-咪唑-2-硫酮 在 双氧水 、 ortho-tungstic acid 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以82%的产率得到[3-(4-溴苄基)-3H-咪唑-4-基]甲醇
  参考文献：
  名称：

  1-取代-5-羟甲基咪唑衍生物的高效合成：2-巯基的清洁氧化裂解1

  摘要：

  1-取代-5-羟甲基咪唑是通过在催化量的过渡金属催化剂存在下，用30%的过氧化氢处理其2-巯基衍生物的绿色脱硫制备的。

  DOI：

  10.1021/op020015c

文献信息

• AZOLE HETEROCYCLIC COMPOUND, PREPARATION METHOD, PHARMACEUTICAL COMPOSITION AND USE
  申请人：Shanghai Institute of Materia Medica, Chinese Academy of Sciences

  公开号：EP2725024A1

  公开（公告）日：2014-04-30

  The present invention relates to the filed of pharmarcutical chemistry, and in particular, to a novel class of azole compounds represented by general formula (I), (II) or (III) amd a preparation method thereof, a pharmarcutical composition with the compounds as active components, and a use of the azole compounds and the pharmarcutical composition in the preparation of a medicament for treatment of diseases associated with Lp-PLA2 enzyme activities, wherein each substituent is as deinfed in the specifictaion.

  本发明涉及药物化学领域，特别是一种由一般式（I）、（II）或（III）表示的新型类唑化合物，以及其制备方法，以这些化合物为活性成分的药物组合物，以及在制备用于治疗与Lp-PLA2酶活性相关疾病的药物中使用这些唑化合物和药物组合物的用途，其中每个取代基如规范中所定义。
• Process for preparing a 1-substituted 5-hydroxymethyl imidazole
  申请人：LG Chem Investment Ltd.

  公开号：US06630593B1

  公开（公告）日：2003-10-07

  A process for preparing a 1-substituted 5-hydroxymethylimidazole of the formula: , wherein R represents alkyl, hydroxyalkyl, allyl, or substituted or unsubstituted arylmethyl or diarylmethyl, comprising the step of reacting a 1-substituted 2-mercapto-5-hydroxymethylimidazole of the formula: , wherein R is as defined above, in the presence of a transition metal catalyst and an oxidizing agent in a solvent.

  一种制备式I所示1-取代的5-羟甲基咪唑的方法：，其中R代表烷基、羟烷基、烯丙基或取代或未取代的芳甲基或二芳甲基，该方法包括以下步骤：在过渡金属催化剂和氧化剂的存在下，于溶剂中反应式II所示1-取代的2-巯基-5-羟甲基咪唑：，其中R如上定义。
• Imidazole derivatives having an inhibitory activity for farnesyl transferase and process for preparation thereof
  申请人：LG Chemical Ltd.

  公开号：US06268363B1

  公开（公告）日：2001-07-31

  The present invention relates to a novel imidazole derivative represented by formula (1) which shows an inhibitory activity against farnesyl transferase or pharmaceutically acceptable salts or isomers thereof, in which A, n1 and Y are defined in the specification; to a process for preparation of the compound of formula (1); to intermediates which are used in the preparation of the compound of formula (1); and to a pharmaceutical composition comprising the compound of formula (1) as an active ingredient.

  本发明涉及一种新型咪唑衍生物，其化学式表示为（1），该化合物对法尼基转移酶具有抑制活性，或者其药学上可接受的盐或同分异构体，其中A、n1和Y在规范中有定义；制备化合物（1）的方法；用于制备化合物（1）的中间体；以及包含化合物（1）作为活性成分的药物组合物。
• Preparation of a clinically investigated ras farnesyl transferase inhibitor
  作者：Peter E. Maligres、Marjorie S. Waters、Steven A. Weissman、J. Christopher McWilliams、Stephanie Lewis、Jennifer Cowen、Robert A. Reamer、R. P. Volante、Paul J. Reider、David Askin

  DOI：10.1002/jhet.5570400206

  日期：2003.3

  The 1,5-disubstituted imidazole system was regioselectively assembled via an improved Marckwald imidazole synthesis. A new imidazole dethionation procedure has been developed to convert the Marckwald mercaptoim-idazole product to the desired imidazole. This methodology was found to be tolerant of a variety of functional groups providing good to excellent yields of 1,5-disubstituted imidazoles. A new

  ras法呢基蛋白转移酶抑制剂1的合成以多千克为单位进行了描述。反合成分析表明，氯甲基咪唑2和哌嗪酮3是可行的前体。1，5-二取代的咪唑系统是通过改进的Marckwald咪唑合成进行区域选择性组装的。已经开发了一种新的咪唑脱硫方法，以将Marckwald巯基咪唑-咪唑产品转化为所需的咪唑。发现该方法耐受各种官能团，从而提供良好至极好的1，5-二取代的咪唑收率。开发了一种新的Mitsunobu环化策略以制备芳基哌嗪酮片段3。
• Efficient Synthesis of 1-Substituted-5-Hydroxymethylimidazole Derivatives:  Clean Oxidative Cleavage of 2-Mercapto Group¹
  作者：Jay Hyok Chang、Kyu Woong Lee、Do Hyun Nam、Won Sup Kim、Hyunik Shin

  DOI：10.1021/op020015c

  日期：2002.9.1

  1-Substituted-5-hydroxymethylimidazoles were prepared through green desulfurization of their 2-mercapto derivatives by the treatment of 30% hydrogen peroxide in the presence of a catalytic amount of transition metal catalysts.

  1-取代-5-羟甲基咪唑是通过在催化量的过渡金属催化剂存在下，用30%的过氧化氢处理其2-巯基衍生物的绿色脱硫制备的。