2-(hexadecyloxy(hydroxy)phosphoryloxy)ethyl pyrrolidine-1-carbodithioate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 2-(hexadecyloxy(hydroxy)phosphoryloxy)ethyl pyrrolidine-1-carbodithioate
• 英文别名: 2-[Hexadecoxy(hydroxy)phosphoryl]oxyethyl pyrrolidine-1-carbodithioate；2-[hexadecoxy(hydroxy)phosphoryl]oxyethyl pyrrolidine-1-carbodithioate
• 化学式: C₂₃H₄₆NO₄PS₂
• 分子量: 495.728
• InChiKey: BQMXFRCGPXIWOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  31
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-bromoethyl hexadecyl hydrogen phosphate 、 sodium pyrrolidine-N-carbodithioate 以 甲醇 为溶剂， 反应 3.0h， 以75%的产率得到2-(hexadecyloxy(hydroxy)phosphoryloxy)ethyl pyrrolidine-1-carbodithioate
  参考文献：
  名称：

  Novel alkylphospholipid-DTC hybrids as promising agents against endocrine related cancers acting via modulation of Akt-pathway

  摘要：

  A new series of 2-(alkoxy(hydroxy)phosphoryloxy)ethyl dialkylcarbodithioate derivatives was synthesized and evaluated against endocrine related cancers, acting via modulation of Akt-pathway. Eighteen compounds were active at 7.24-100 mu M against MDA-MB-231 or MCF-7 cell lines of breast cancer. Three compounds (14, 18 and 22) were active against MCF-7 cells at IC50 significantly better than miltefosine and most of the compounds were less toxic towards non-cancer cell lines, HEK-293. On the other hand, twelve compounds exhibited cell growth inhibiting activity against prostate cancer cell lines, either PC-3 or DU-145 at 14.69-95.20 mu M. While nine of these were active against both cell lines. The most promising compounds 14 and 18 were about two and five fold more active than miltefosine against DU-145 and MCF-7 cell lines respectively and significantly down regulated phospho-Akt. Possibly anti-cancer and pro-apoptotic activity was mostly due to blockade of Akt-pathway. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.028

文献信息

• Novel alkylphospholipid-DTC hybrids as promising agents against endocrine related cancers acting via modulation of Akt-pathway
  作者：Santosh Jangir、Veenu Bala、Nand Lal、Lalit Kumar、Amit Sarswat、Amit Kumar、Hamidullah、Karan S. Saini、Vikas Sharma、Vikas Verma、Jagdamba P. Maikhuri、Rituraj Konwar、Gopal Gupta、Vishnu L. Sharma

  DOI：10.1016/j.ejmech.2014.08.028

  日期：2014.10

  A new series of 2-(alkoxy(hydroxy)phosphoryloxy)ethyl dialkylcarbodithioate derivatives was synthesized and evaluated against endocrine related cancers, acting via modulation of Akt-pathway. Eighteen compounds were active at 7.24-100 mu M against MDA-MB-231 or MCF-7 cell lines of breast cancer. Three compounds (14, 18 and 22) were active against MCF-7 cells at IC50 significantly better than miltefosine and most of the compounds were less toxic towards non-cancer cell lines, HEK-293. On the other hand, twelve compounds exhibited cell growth inhibiting activity against prostate cancer cell lines, either PC-3 or DU-145 at 14.69-95.20 mu M. While nine of these were active against both cell lines. The most promising compounds 14 and 18 were about two and five fold more active than miltefosine against DU-145 and MCF-7 cell lines respectively and significantly down regulated phospho-Akt. Possibly anti-cancer and pro-apoptotic activity was mostly due to blockade of Akt-pathway. (C) 2014 Elsevier Masson SAS. All rights reserved.