(3β)-3-hydroxypregn-5-en-20-one 4-{4-[di(2-chloroethyl)amino]phenyl}butyrate | 1085269-21-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3β)-3-hydroxypregn-5-en-20-one 4-{4-[di(2-chloroethyl)amino]phenyl}butyrate
• 英文别名: pregnenolone chlorambucil ester；[(3S,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoate
• CAS: 1085269-21-1
• 化学式: C₃₅H₄₉Cl₂NO₃
• 分子量: 602.685
• InChiKey: HPNQWTQZANXCJA-VPGALUENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3β)-3-hydroxypregn-5-en-20-one 4-{4-[di(2-chloroethyl)amino]phenyl}butyrate 在 porcine liver esterase 、 disodium hydrogenphosphate 、 sodium dihydrogenphosphate 、 potassium chloride 、 sodium chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 苯丁酸氮芥
  参考文献：
  名称：

  To determine the cytotoxicity of chlorambucil and one of its nitro-derivatives, conjugated to prasterone and pregnenolone, towards eight human cancer cell-lines

  摘要：

  Four ester prodrugs derived from the bifunctional alkylating agent chlorambucil, and one of its nitro-derivatives, 3-nitrochlorambucil conjugated to prasterone and pregnenolone, were synthesized and tested for their cytotoxic activity against eight human cell lines, using the standard MTT assay. A comparison between the esters and the controls, namely chlorambucil and 3-nitrochlorambucil would suggest that all four esters possess to varying degrees, specificity towards the breast adenocarcinoma cell line (MDA-mb468) than the other seven cells' lines tested. The overall findings are encouraging since it infers that these lipophilic esters not only have the ability to traverse specific cell membranes but also exhibit cytotoxicity towards most of the cell lines tested. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.11.014
• 作为产物：
  描述：

  孕烯醇酮 、 苯丁酸氮芥 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以60%的产率得到(3β)-3-hydroxypregn-5-en-20-one 4-{4-[di(2-chloroethyl)amino]phenyl}butyrate
  参考文献：
  名称：

  To determine the cytotoxicity of chlorambucil and one of its nitro-derivatives, conjugated to prasterone and pregnenolone, towards eight human cancer cell-lines

  摘要：

  Four ester prodrugs derived from the bifunctional alkylating agent chlorambucil, and one of its nitro-derivatives, 3-nitrochlorambucil conjugated to prasterone and pregnenolone, were synthesized and tested for their cytotoxic activity against eight human cell lines, using the standard MTT assay. A comparison between the esters and the controls, namely chlorambucil and 3-nitrochlorambucil would suggest that all four esters possess to varying degrees, specificity towards the breast adenocarcinoma cell line (MDA-mb468) than the other seven cells' lines tested. The overall findings are encouraging since it infers that these lipophilic esters not only have the ability to traverse specific cell membranes but also exhibit cytotoxicity towards most of the cell lines tested. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.11.014