1-(4-bromobenzyl)-5-(chloromethyl)-1H-imidazole | 742045-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-bromobenzyl)-5-(chloromethyl)-1H-imidazole
• 英文别名: 1-[(4-Bromophenyl)methyl]-5-(chloromethyl)imidazole
• CAS: 742045-40-5
• 化学式: C₁₁H₁₀BrClN₂
• 分子量: 285.571
• InChiKey: DBEMRCWBLNINIV-UHFFFAOYSA-N

物化性质

• 沸点：
  433.7±30.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-bromobenzyl)-5-(chloromethyl)-1H-imidazole 在 四(三苯基膦)钯 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 乙二醇二甲醚 、 水 、 乙腈 为溶剂， 生成 1-(3-Chlorophenyl)-4-[[3-[[4-(3,5-dichlorophenyl)phenyl]methyl]imidazol-4-yl]methyl]piperazin-2-one
  参考文献：
  名称：

  Potent inhibitors of farnesyltransferase and geranylgeranyltransferase-I

  摘要：

  Compound 1 has been shown to be a dual prenylation inhibitor with FPTase (IC50 = 2 nM) and GGPTase-1 (IC50 = 95 nM). Analogues of 1, which replaced the cyanophenyl group with various biaryls, led to the discovery of highly potent dual FPTase/GGPTase-1 inhibitors. 4-Trifluoromethylphenyl, trifluoropentynyl, and trifluoropentyl were identified as good p-cyano replacements. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00154-3
• 作为产物：
  描述：

  4-溴苄胺盐酸盐 在 pyridine-SO3 complex 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 1,2-二氯乙烷 、 正丁醇 为溶剂， 生成 1-(4-bromobenzyl)-5-(chloromethyl)-1H-imidazole
  参考文献：
  名称：

  Potent inhibitors of farnesyltransferase and geranylgeranyltransferase-I

  摘要：

  Compound 1 has been shown to be a dual prenylation inhibitor with FPTase (IC50 = 2 nM) and GGPTase-1 (IC50 = 95 nM). Analogues of 1, which replaced the cyanophenyl group with various biaryls, led to the discovery of highly potent dual FPTase/GGPTase-1 inhibitors. 4-Trifluoromethylphenyl, trifluoropentynyl, and trifluoropentyl were identified as good p-cyano replacements. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00154-3

文献信息

• Synthesis of a¹⁴C-labeled FPTase inhibitor<i>via</i>a Pd-catalyzed cyanation with Zn(¹⁴CN)₂and<i>via</i>bromo[¹⁴C]acetic acid
  作者：Jonathan Z. Ho、Charles S. Elmore、Matthew P. Braun

  DOI：10.1002/jlcr.1545

  日期：2008.10.30

  14C-Labeled farnesyl-protein transferase inhibitor 1a was required for drug metabolism studies. The first approach was to synthesize 14C-labeled 1b using Zn(14CN)2 in a Pd-catalyzed cyanation. A second approach was to prepare labeled 1c with the 14C-label in the piperazine ring. All metabolites from 1b were non-radioactive whereas the same metabolites from 1c were all radioactive and quantifiable. Copyright © 2008 John Wiley & Sons, Ltd.

  药物代谢研究需要 14C 标记的法尼基蛋白转移酶抑制剂 1a。第一种方法是在 Pd 催化氰化反应中使用 Zn(14CN)2 合成 14C 标记的 1b。第二种方法是制备在哌嗪环上带有 14C 标记的标记 1c。 1b 中的所有代谢物均无放射性，而 1c 中的相同代谢物均具有放射性且可定量。版权所有 © 2008 约翰·威利父子有限公司
• Potent inhibitors of farnesyltransferase and geranylgeranyltransferase-I
  作者：Diem N. Nguyen、Craig A. Stump、Eileen S. Walsh、Christine Fernandes、Joseph P. Davide、Michelle Ellis-Hutchings、Ronald G. Robinson、Theresa M. Williams、Robert B. Lobell、Hans E. Huber、Carolyn A. Buser

  DOI：10.1016/s0960-894x(02)00154-3

  日期：2002.5

  Compound 1 has been shown to be a dual prenylation inhibitor with FPTase (IC50 = 2 nM) and GGPTase-1 (IC50 = 95 nM). Analogues of 1, which replaced the cyanophenyl group with various biaryls, led to the discovery of highly potent dual FPTase/GGPTase-1 inhibitors. 4-Trifluoromethylphenyl, trifluoropentynyl, and trifluoropentyl were identified as good p-cyano replacements. (C) 2002 Published by Elsevier Science Ltd.