1-(4-甲基苄基)-1H-5-羟甲基咪唑 | 226931-22-2

• 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: 1-(4-甲基苄基)-1H-5-羟甲基咪唑
• 英文名称: 1-(4-methylbenzyl)-1H-5-hydroxymethylimidazole
• 英文别名: 5-Hydroxymethyl-1(4-methylbenzyl)imidazole；[3-[(4-Methylphenyl)methyl]imidazol-4-yl]methanol
• CAS: 226931-22-2
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: WLXZXEGYNXXTTF-UHFFFAOYSA-N

物化性质

• 熔点：
  136-138 °C
• 沸点：
  412.1±30.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-甲基苄基)-1H-5-羟甲基咪唑 在 manganese(IV) oxide 、 3 A molecular sieve 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 25.0h， 生成 methyl (2S)-2-[benzoyl-[1-[[3-[(4-methylphenyl)methyl]imidazol-4-yl]methyl]piperidin-4-yl]amino]-4-methylsulfanylbutanoate
  参考文献：
  名称：

  Potent and Selective Farnesyl Transferase Inhibitors

  摘要：

  We recently described a novel series of CA(1)A(2)X peptidomimetics as farnesyl transferase inhibitors (FTIs). These compounds possess an N-(4-piperidinyl)benzamide scaffold mimicking A(1)A(2) residue. Extensive exploration of structure-activity relationships revealed that replacement of cysteine by substituted benzylimidazoles provided nanomolar FTIs with in vitro activities (18e, IC50 = 4.60 nM on isolated enzyme, EC50 = 20.0 nM for growth inhibition on a tumor cell line). The molecular docking of 18e and 19e in the active site of the enzyme provided details of key interactions with the protein and showed that the methionine or phenylalanine residue fits into the aryl binding site.

  DOI：

  10.1021/jm030502y
• 作为产物：
  描述：

  [1-(4-methylbenzyl)-1H-5-imidazolyl]methyl acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以99%的产率得到1-(4-甲基苄基)-1H-5-羟甲基咪唑
  参考文献：
  名称：

  Potent and Selective Farnesyl Transferase Inhibitors

  摘要：

  We recently described a novel series of CA(1)A(2)X peptidomimetics as farnesyl transferase inhibitors (FTIs). These compounds possess an N-(4-piperidinyl)benzamide scaffold mimicking A(1)A(2) residue. Extensive exploration of structure-activity relationships revealed that replacement of cysteine by substituted benzylimidazoles provided nanomolar FTIs with in vitro activities (18e, IC50 = 4.60 nM on isolated enzyme, EC50 = 20.0 nM for growth inhibition on a tumor cell line). The molecular docking of 18e and 19e in the active site of the enzyme provided details of key interactions with the protein and showed that the methionine or phenylalanine residue fits into the aryl binding site.

  DOI：

  10.1021/jm030502y

文献信息

• 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。
• IMIDAZOLE DERIVATIVES HAVING AN INHIBITORY ACTIVITY FOR FARNESYL TRANSFERASE AND PROCESS FOR PREPARATION THEREOF
  申请人：LG CHEMICAL LIMITED

  公开号：EP1045846B1

  公开（公告）日：2003-05-02
• US6268363B1
  申请人：——

  公开号：US6268363B1

  公开（公告）日：2001-07-31
• US6472526B1
  申请人：——

  公开号：US6472526B1

  公开（公告）日：2002-10-29
• US6518429B2
  申请人：——

  公开号：US6518429B2

  公开（公告）日：2003-02-11