iodomethyl 8-(tert-butoxycarbonylamino)-1-octyl carbonate | 626230-84-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: iodomethyl 8-(tert-butoxycarbonylamino)-1-octyl carbonate
• 英文别名: Iodomethyl 8-[(2-methylpropan-2-yl)oxycarbonylamino]octyl carbonate
• CAS: 626230-84-0
• 化学式: C₁₅H₂₈INO₅
• 分子量: 429.296
• InChiKey: ABZBGJLCEUQOAB-UHFFFAOYSA-N

物化性质

• 沸点：
  447.6±30.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  iodomethyl 8-(tert-butoxycarbonylamino)-1-octyl carbonate 在 盐酸 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 0.33h， 生成 8-aminooctyl [4-[[N'-[6-(4-chlorophenoxy)hexyl]-N-cyanocarbamimidoyl]amino]pyridin-1-ium-1-yl]methyl carbonate;chloride
  参考文献：
  名称：

  EB1627: a soluble prodrug of the potent anticancer cyanoguanidine CHS828

  摘要：

  To overcome pharmacokinetic and solubility problems observed in early clinical trials with the potent anticancer compound CHS828, we synthesised a series of prodrugs with improved properties. The best compound obtained was EB1627, with a tetraethyleneglycol moiety attached to the parent drug via a carbonate linkage. This compound was found soluble enough to be given i.v. and the drug was rapidly released in vivo exerting a very potent inhibitory activity alone and in combination with known cytostatics (etoposide) in animal models in vivo. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.064
• 作为产物：
  描述：

  tert-butyl (8-hydroxyoctyl)carbamate 在 吡啶 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 iodomethyl 8-(tert-butoxycarbonylamino)-1-octyl carbonate
  参考文献：
  名称：

  EB1627: a soluble prodrug of the potent anticancer cyanoguanidine CHS828

  摘要：

  To overcome pharmacokinetic and solubility problems observed in early clinical trials with the potent anticancer compound CHS828, we synthesised a series of prodrugs with improved properties. The best compound obtained was EB1627, with a tetraethyleneglycol moiety attached to the parent drug via a carbonate linkage. This compound was found soluble enough to be given i.v. and the drug was rapidly released in vivo exerting a very potent inhibitory activity alone and in combination with known cytostatics (etoposide) in animal models in vivo. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.064

文献信息

• [EN] CYANOGUANIDINE PRODRUGS<br/>[FR] PROMEDICAMENTS DE CYANOGUANIDINE
  申请人：LEO PHARMA AS

  公开号：WO2003097601A1

  公开（公告）日：2003-11-27

  Pyridyl cyanoguanidine compounds of the general formula I wherein A, X1, X2, X3, Y1, Y2, Y3, R1, R2, R5, R6 and n are as indicated in the description are suitable as prodrugs in human and veterinary therapy of proliferative diseases such as cancers.

  通用式I中的吡啶基氰胍化合物，其中A、X1、X2、X3、Y1、Y2、Y3、R1、R2、R5、R6和n如描述中所示，适用于作为前药在人类和兽医治疗增殖性疾病如癌症中使用。