p-phenylessigsaeureethylester | 31386-35-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: p-phenylessigsaeureethylester
• 英文别名: {4-[bis-(2-chloro-ethyl)-amino]-phenyl}-acetic acid ethyl ester；{4-[Bis-(2-chlor-aethyl)-amino]-phenyl}-essigsaeure-aethylester；Ethyl (p-(bis(2-chloroethyl)amino)phenyl)acetate；ethyl 2-[4-[bis(2-chloroethyl)amino]phenyl]acetate
• CAS: 31386-35-3
• 化学式: C₁₄H₁₉Cl₂NO₂
• 分子量: 304.216
• InChiKey: XTWPHUBWNUSDMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  p-phenylessigsaeureethylester 在 盐酸 、 水 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2-(4-(bis(2-chloroethyl)amino)phenyl)-N-(2-((4-(4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-1,2,5-oxadiazol-3-yl)amino)ethyl)acetamide
  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
• 作为产物：
  描述：

  对硝基苯乙腈 在 盐酸 、 硫酸 、 铁粉 、 氯化铵 、 溶剂黄146 、 三氯氧磷 作用下， 生成 p-phenylessigsaeureethylester
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel sesquiterpene mustards as potential anticancer agents

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2015.03.001

文献信息

• Synthesis of androstene oxime-nitrogen mustard bioconjugates as potent antineoplastic agents
  作者：Pratap Chandra Acharya、Ranju Bansal

  DOI：10.1016/j.steroids.2017.04.005

  日期：2017.7

  their alkylating activity was investigated by the in vitro colorimetric 4-(p-nitrobenzyl)pyridine (NBP) assay. The 17E-steroidal oxime-benzoic acid mustard ester 3β-acetoxy-17E-[p-(N,N-bis(2-chloroethyl)amino)]benzoyloxyimino-androst-5-ene (8) emerged as the most potent conjugate having significant cytotoxicity on most of the NCI 60-cell lines. Outstanding growth inhibition was observed on the IGROV1 ovarian

  在本研究中，首次报道了各种甾族肟的苯乙酸和苯甲酸氮芥子气共轭物的合成和抗肿瘤活性。通过更稳定的肟酯键实现缀合，并在各种人类癌细胞系上体外评估所得新合成的缀合物的细胞毒性。通过体外比色4-（对硝基苄基）吡啶（NBP）测定法研究了其烷基化活性的程度。17E-甾族肟-苯甲酸芥末酯3β-乙酰氧基-17E- [对-（N，N-双（2-氯乙基）氨基）]苯甲酰氧基亚氨基-雄烯基-5-烯（8）成为最有效的偶联物，具有对大多数NCI 60细胞株具有明显的细胞毒性。在IGROV1卵巢癌细胞系中观察到杰出的生长抑制，GI50 = 0.937µM。一般来说，
• Everett et al., Journal of the Chemical Society, 1953, p. 2386,2387
  作者：Everett et al.

  DOI：——

  日期：——