tert-butyl 4,5-bis(tert-butyldimethylsilyloxymethyl)-1-methyl-1H-imidazol-2-ylcarbamate | 263159-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl 4,5-bis(tert-butyldimethylsilyloxymethyl)-1-methyl-1H-imidazol-2-ylcarbamate
• CAS: 263159-51-9
• 化学式: C₂₃H₄₇N₃O₄Si₂
• 分子量: 485.815
• InChiKey: OHBLMEHAYFCMIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.81
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  74.61
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4,5-bis(tert-butyldimethylsilyloxymethyl)-1-methyl-1H-imidazol-2-ylcarbamate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到tert-butyl 4,5-bis(hydroxymethyl)-1-methyl-1H-imidazol-2-ylcarbamate
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Imidazolylmethyl Carbamate Prodrugs of Alkylating Agents

  摘要：

  Two approaches to prodrugs of alkylating agents based on an imidazolylmethyl carbamate nucleus were explored. A 2-azido analogue (3) of the bis-carbamate carmethizole (1) displayed similar aerobic cytotoxicity to 1 in a panel of human and murine cell lines. Approaches to the 2-amino and 2-carbamoyl analogues are described. In the second approach an imidazolylmethanol was used as a 'trigger' linked via a carbamate to the alkylating agent N,N-bis(2-chlorethyl)amine (BCEA). Nitroimidazole and methylsulphinylimidazole carbamate prodrugs 6-8 were 5-20-fold less toxic than BCEA. Despite this deactivation in the prodrug form, little increase in cytotoxicity was observed under hypoxia. The data suggest that BCEA released on bioreduction is not sufficiently potent to contribute significant additional cytotoxicity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01031-5
• 作为产物：
  描述：

  1H-咪唑-4,5-二甲酸二乙酯 在 palladium on activated charcoal 咪唑 、 lithium aluminium tetrahydride 、 正丁基锂 、 对甲苯磺酰叠氮 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~40.0 ℃ 、413.68 kPa 条件下， 反应 128.0h， 生成 tert-butyl 4,5-bis(tert-butyldimethylsilyloxymethyl)-1-methyl-1H-imidazol-2-ylcarbamate
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Imidazolylmethyl Carbamate Prodrugs of Alkylating Agents

  摘要：

  Two approaches to prodrugs of alkylating agents based on an imidazolylmethyl carbamate nucleus were explored. A 2-azido analogue (3) of the bis-carbamate carmethizole (1) displayed similar aerobic cytotoxicity to 1 in a panel of human and murine cell lines. Approaches to the 2-amino and 2-carbamoyl analogues are described. In the second approach an imidazolylmethanol was used as a 'trigger' linked via a carbamate to the alkylating agent N,N-bis(2-chlorethyl)amine (BCEA). Nitroimidazole and methylsulphinylimidazole carbamate prodrugs 6-8 were 5-20-fold less toxic than BCEA. Despite this deactivation in the prodrug form, little increase in cytotoxicity was observed under hypoxia. The data suggest that BCEA released on bioreduction is not sufficiently potent to contribute significant additional cytotoxicity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01031-5