4-Hydroxymethyl-5-butylimidazole | 59973-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-Hydroxymethyl-5-butylimidazole
• 英文别名: (4-butyl-1H-imidazol-5-yl)methanol
• CAS: 59973-29-4
• 化学式: C₈H₁₄N₂O
• 分子量: 154.212
• InChiKey: RIUZCJIFIIOBEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Hydroxymethyl-5-butylimidazole 在 manganese(IV) oxide 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 16.0h， 生成 (3Z,6Z)-3-benzylidene-6-((5-butyl-1H-imidazol-4-yl)methylene)piperazine-2,5-dione
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationship Study of Antimicrotubule Agents Phenylahistin Derivatives with a Didehydropiperazine-2,5-dione Structure

  摘要：

  Plinabulin (11, NPI-2358) is a potent microtubule-targeting agent derived from the natural diketopiperazine "phenylahistin" (1) with a colchicine-like tubulin depolymerization activity. Compound 11 was recently developed as VDA and is now under phase II clinical trials as an anticancer drug. To develop more potent antimicrotubule and cytotoxic derivatives based on the didehydro-DKP skeleton, we performed further modification on the tert-butyl or phenyl groups of 11, and evaluated their cytotoxic and tubulin-binding activities. In the SAR study, we developed more potent derivatives 33 with 2,5-difluorophenyl and 50 with activity of 33 and 50 exhibited a lowest effective concentration The values of 33 and 50 were 5 and 10 times more potent than second-generation derivative with both vascular disrupting and a benzophenone in place of the phenyl group. The anti-HuVEC of 2 and 1 nM for microtubule depolymerization, respectively. that of CA-4, respectively. These derivatives could be a valuable cytotoxic activities.

  DOI：

  10.1021/jm2009088
• 作为产物：
  描述：

  戊酸酐 在 lithium aluminium tetrahydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 4-Hydroxymethyl-5-butylimidazole
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationship Study of Antimicrotubule Agents Phenylahistin Derivatives with a Didehydropiperazine-2,5-dione Structure

  摘要：

  Plinabulin (11, NPI-2358) is a potent microtubule-targeting agent derived from the natural diketopiperazine "phenylahistin" (1) with a colchicine-like tubulin depolymerization activity. Compound 11 was recently developed as VDA and is now under phase II clinical trials as an anticancer drug. To develop more potent antimicrotubule and cytotoxic derivatives based on the didehydro-DKP skeleton, we performed further modification on the tert-butyl or phenyl groups of 11, and evaluated their cytotoxic and tubulin-binding activities. In the SAR study, we developed more potent derivatives 33 with 2,5-difluorophenyl and 50 with activity of 33 and 50 exhibited a lowest effective concentration The values of 33 and 50 were 5 and 10 times more potent than second-generation derivative with both vascular disrupting and a benzophenone in place of the phenyl group. The anti-HuVEC of 2 and 1 nM for microtubule depolymerization, respectively. that of CA-4, respectively. These derivatives could be a valuable cytotoxic activities.

  DOI：

  10.1021/jm2009088

文献信息

• Process of reduction
  申请人：Smith Kline & French Laboratories Limited

  公开号：US03984293A1

  公开（公告）日：1976-10-05

  An electrochemical process for preparing 4-(hydroxymethyl)-imidazoles, which are useful as chemical intermediates.

  一种电化学过程，用于制备4-(羟甲基)-咪唑，这些化合物可作为化学中间体。