1-(hexylamino)-3-[4-[7-[3-(hexylamino)-2-hydroxypropoxy]-2H-chromen-3-yl]phenoxy]propan-2-ol | 1428323-43-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 1-(hexylamino)-3-[4-[7-[3-(hexylamino)-2-hydroxypropoxy]-2H-chromen-3-yl]phenoxy]propan-2-ol
• CAS: 1428323-43-6
• 化学式: C₃₃H₅₀N₂O₅
• 分子量: 554.77
• InChiKey: YFAJXXRFGNPCDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  92.2
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  正己胺 、 7-(oxiran-2-ylmethoxy)-3-(4-(oxiran-2-ylmethoxy)phenyl)-2H-chromene 反应 24.0h， 以63%的产率得到1-(hexylamino)-3-[4-[7-[3-(hexylamino)-2-hydroxypropoxy]-2H-chromen-3-yl]phenoxy]propan-2-ol
  参考文献：
  名称：

  Synthesis of novel isoflavene–propranolol hybrids as anti-tumor agents

  摘要：

  Isoflavene-propranolol hybrid molecules were developed as potentially novel anti-tumour agents. Isoflavene itself has potent anti-cancer activity while propranolol can enhance anti-proliferative and anti-angiogenic properties of 5-fluorouracil and paclitaxel. The hybrids were produced via nucleophilic addition of substituted amine groups to a dioxiran intermediate, which was in turn generated from the Williamson-type reaction of isoflavene with (+/-)-epichlorohydrin. These analogues were tested in anti-cancer cell viability assays against SHEP neuroblastoma and MDA-MB-231 breast adenocarcinoma cell lines, and were found to exhibit potent anti-proliferative activities. These compounds also displayed anti-angiogenic and anti-proliferative effects in HMEC-1 human microvascular endothelial cell lines. Notably, the most potent hybrid molecules synthesized in this work showed enhanced potency against cancer cell lines compared to either isoflavene or propranolol alone, while retaining significant selectivity for cancer cells over MRC-5 normal lung fibroblast cells. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.059

文献信息

• Synthesis of novel isoflavene–propranolol hybrids as anti-tumor agents
  作者：Eugene M.H. Yee、Eddy Pasquier、George Iskander、Kasey Wood、David StC Black、Naresh Kumar

  DOI：10.1016/j.bmc.2013.01.059

  日期：2013.4

  Isoflavene-propranolol hybrid molecules were developed as potentially novel anti-tumour agents. Isoflavene itself has potent anti-cancer activity while propranolol can enhance anti-proliferative and anti-angiogenic properties of 5-fluorouracil and paclitaxel. The hybrids were produced via nucleophilic addition of substituted amine groups to a dioxiran intermediate, which was in turn generated from the Williamson-type reaction of isoflavene with (+/-)-epichlorohydrin. These analogues were tested in anti-cancer cell viability assays against SHEP neuroblastoma and MDA-MB-231 breast adenocarcinoma cell lines, and were found to exhibit potent anti-proliferative activities. These compounds also displayed anti-angiogenic and anti-proliferative effects in HMEC-1 human microvascular endothelial cell lines. Notably, the most potent hybrid molecules synthesized in this work showed enhanced potency against cancer cell lines compared to either isoflavene or propranolol alone, while retaining significant selectivity for cancer cells over MRC-5 normal lung fibroblast cells. (C) 2013 Elsevier Ltd. All rights reserved.