3-{4-[bis-(2-hydroxy-ethyl)-amino]-phenyl}-propionic acid ethyl ester | 124673-89-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-{4-[bis-(2-hydroxy-ethyl)-amino]-phenyl}-propionic acid ethyl ester
• 英文别名: 3-{4-[Bis-(2-hydroxy-aethyl)-amino]-phenyl}-propionsaeure-aethylester
• CAS: 124673-89-8
• 化学式: C₁₅H₂₃NO₄
• 分子量: 281.352
• InChiKey: XWPXXOCMOUEDLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  160-170 °C(Press: 1 Torr)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  20.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  70.0
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-{4-[bis-(2-hydroxy-ethyl)-amino]-phenyl}-propionic acid ethyl ester 在 4-二甲氨基吡啶 、 氯化亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 (3R,5aS,6R,8aS,9R,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl 3-(4-(bis(2-chloroethyl)amino)phenyl)propanoate
  参考文献：
  名称：

  Novel nitrogen mustard-artemisinin hybrids with potent anti-leukemia action through DNA damage and activation of GPx

  摘要：

  DOI：

  10.1016/j.ejmech.2022.114783
• 作为产物：
  描述：

  3-(4-硝基苯基)丙酸 在 硫酸 、 palladium on activated charcoal 、 氢气 、 溶剂黄146 作用下， 反应 12.0h， 生成 3-{4-[bis-(2-hydroxy-ethyl)-amino]-phenyl}-propionic acid ethyl ester
  参考文献：
  名称：

  通过双重靶向IDO1和DNA提高癌症免疫疗法的效力

  摘要：

  在此，我们报告了首次探索双重靶向药物设计策略以提高小分子癌症免疫疗法的功效。合理设计了吲哚胺2，3-二加氧酶1（IDO1）抑制剂和分别将IDO1和DNA分别靶向氮芥的DNA烷基化杂种。作为此类分子的首例，它们在体外和体内均显示出显着增强的抗癌活性，且毒性低。这项概念验证研究为开发新型有效的免疫疗法治疗癌症迈出了关键的一步。

  DOI：

  10.1002/cmdc.201700666

文献信息

• Design, synthesis and biological evaluation of novel sesquiterpene mustards as potential anticancer agents
  作者：Yuan-Zhen Xu、Xue-Yan Gu、Shou-Jiao Peng、Jian-Guo Fang、Ying-Mei Zhang、De-Jun Huang、Jian-Jun Chen、Kun Gao

  DOI：10.1016/j.ejmech.2015.03.001

  日期：2015.4

  Several novel series of sesquiterpene mustards (SMs) bearing nitrogen mustard and glutathione (GSH)-reactive alpha-methylene-gamma-butyrolactone groups were successfully prepared for the first time and showed excellent antiproliferative activities in vitro. Among them, compounds 2e and 2g displayed the highest antiproliferative properties with IC50 values ranging from 2.5 to 8.7 mu M. The selectivity of these two compounds was evaluated by SRB method against human cancer and normal hepatic cells (HepG2 and L02). The induction of apoptosis and effects on the cell cycle distribution with compounds 2e and 2g were investigated by Hoechst 33,258 staining and flow cytometry, which exhibited that they could induce selective cell apoptosis and cell cycle arrest in HepG2 and L02 cells. In addition, further investigation showed that compounds 2e and 2g could obviously inhibit the proliferation of HepG2 cells by inducing significant DNA cross-linking and depleting GSH in cell media. The good cytotoxicity and selectivity of compounds 2e and 2g pointed them as promising leads for anticancer drug design. (C) 2015 Published by Elsevier Masson SAS.
• Everett et al., Journal of the Chemical Society, 1953, p. 2386,2387
  作者：Everett et al.

  DOI：——

  日期：——
• Synthesis and biological evaluation of new cytotoxic indazolo[4,3-gh]isoquinolinone derivatives
  作者：Manochehr Shahabi、Eva Schirmer、Karem Shanab、Theerachart Leepasert、Jana Ruzicka、Wolfgang Holzer、Helmut Spreitzer、Babette Aicher、Peter Schmidt、Lars Blumenstein、Gilbert Müller、Eckhard Günther

  DOI：10.1016/j.bmcl.2013.01.022

  日期：2013.3

  A series of indazolo[4,3-gh]isoquinolinones derivatives have been synthesized to decrease cardiotoxic side effects in comparison to Mitoxantrone. The antiproliferative effects of different side chains were investigated and tested on at least four different cell lines of cervix, ovarian, CNS, NSCLC (non-small-cell lung cancer) and colon carcinoma. In addition to antiproliferative activities, influence on cell cycle and intercalation behavior have been tested. (C) 2013 Elsevier Ltd. All rights reserved.