4-(1-[(4-bromophenyl)methyl]imidazol-5-ylmethyl)-1-(3-chlorophenyl)piperazin-2-one | 312936-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-(1-[(4-bromophenyl)methyl]imidazol-5-ylmethyl)-1-(3-chlorophenyl)piperazin-2-one
• 英文别名: 4-[[3-[(4-Bromophenyl)methyl]imidazol-4-yl]methyl]-1-(3-chlorophenyl)piperazin-2-one
• CAS: 312936-83-7
• 化学式: C₂₁H₂₀BrClN₄O
• 分子量: 459.773
• InChiKey: GGVXBMUOFOEEFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  41.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-二氯苯硼酸 、 4-(1-[(4-bromophenyl)methyl]imidazol-5-ylmethyl)-1-(3-chlorophenyl)piperazin-2-one 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 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 、 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 、 乙腈 、 正丁醇 为溶剂， 生成 4-(1-[(4-bromophenyl)methyl]imidazol-5-ylmethyl)-1-(3-chlorophenyl)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

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.