ethyl (4-(hydroxymethyl)phenyl)carbonate | 70837-24-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (4-(hydroxymethyl)phenyl)carbonate
• 英文别名: carbonic acid ethyl ester 4-hydroxymethyl-phenyl ester；Ethyl [4-(hydroxymethyl)phenyl] carbonate
• CAS: 70837-24-0
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: ICQZMJRWSKHVGH-UHFFFAOYSA-N

物化性质

• 沸点：
  327.7±34.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (4-(hydroxymethyl)phenyl)carbonate 在 吡啶 、 N-氯代丁二酰亚胺 、 亚磷酸二苯酯 作用下， 以 乙腈 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  抗HIV活性核苷三磷酸前药。

  摘要：

  我们公开了一项关于核苷三磷酸酯（NTP）类似物的研究，其中γ-磷酸酯被两个不同的可生物降解的掩蔽单元和d4T进行了共价修饰，从而使d4TTP在磷酸盐缓冲液（pH 7.3）和酶中具有较高的选择性CD4 + T淋巴细胞CEM细胞提取物中触发的反应。这允许绕过细胞内磷酸化通常所需的所有步骤。这些Tri PPP将包含酰氧基苄基（AB；酯）或烷氧基羰氧基苄基（ACB；碳酸酯）与ACB部分结合的环核苷酸描述为NTP递送系统。这两个不同基团的引入导致通过化学水解，特别是通过细胞提取酶选择性地形成γ-（ACB）-d4TTP。γ-（AB）-d4TTP的裂解速度比γ-（ACB）-d4TTP更快。在抗病毒测定中，这些化合物在野生型CEM / O细胞中具有更强的抗HIV-1和HIV-2活性，更重要的是在缺乏胸苷激酶的CD4 + T细胞（CEM / TK –）中具有很高的活性。

  DOI：

  10.1021/acs.jmedchem.0c00271
• 作为产物：
  描述：

  对羟基苯甲醇 、 氯甲酸乙酯 在 三乙胺 作用下， 以 乙腈 为溶剂， 以79%的产率得到ethyl (4-(hydroxymethyl)phenyl)carbonate
  参考文献：
  名称：

  Iodination of verapamil for a stronger induction of death, through GSH efflux, of cancer cells overexpressing MRP1

  摘要：

  The multidrug resistance protein 1 (MRP1), involved in multidrug resistance (MDR) of cancer cells, was found to be modulated by verapamil, through stimulation of GSH transport, leading to apoptosis of MRP1-overexpressing cells. In this study, various iodinated derivatives of verapamil were synthesized, including iodination on the B ring, known to be involved in verapamil cardiotoxicity, and assayed for the stimulation of GSH efflux by MRP1. The iodination, for nearly all compounds, led to a higher stimulation of GSH efflux. However, determination of concomitant cytotoxicity is also important for selecting the best compound, which was found to be 10-fold more potent than verapamil. This will then allow us to design original anti-cancer compounds which could specifically kill the resistant cancer cells. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.07.031

文献信息

• Minami,N.; Kijima,S., Chemical and pharmaceutical bulletin, 1979, vol. 27, p. 816 - 820
  作者：Minami,N.、Kijima,S.

  DOI：——

  日期：——
• MINAMI NORIO; KIJIMA SHIZUMASA, CHEM. AND PHARM. BULL., 1979, 27, NO 3, 816-820
  作者：MINAMI NORIO、 KIJIMA SHIZUMASA

  DOI：——

  日期：——
• Iodination of verapamil for a stronger induction of death, through GSH efflux, of cancer cells overexpressing MRP1
  作者：Régis Barattin、Thomas Perrotton、Doriane Trompier、Doriane Lorendeau、Attilio Di Pietro、Amaury du Moulinet d’Hardemare、Hélène Baubichon-Cortay

  DOI：10.1016/j.bmc.2010.07.031

  日期：2010.9

  The multidrug resistance protein 1 (MRP1), involved in multidrug resistance (MDR) of cancer cells, was found to be modulated by verapamil, through stimulation of GSH transport, leading to apoptosis of MRP1-overexpressing cells. In this study, various iodinated derivatives of verapamil were synthesized, including iodination on the B ring, known to be involved in verapamil cardiotoxicity, and assayed for the stimulation of GSH efflux by MRP1. The iodination, for nearly all compounds, led to a higher stimulation of GSH efflux. However, determination of concomitant cytotoxicity is also important for selecting the best compound, which was found to be 10-fold more potent than verapamil. This will then allow us to design original anti-cancer compounds which could specifically kill the resistant cancer cells. (C) 2010 Published by Elsevier Ltd.
• Anti-HIV-Active Nucleoside Triphosphate Prodrugs
  作者：Xiao Jia、Dominique Schols、Chris Meier

  DOI：10.1021/acs.jmedchem.0c00271

  日期：2020.6.11

  We disclose a study on nucleoside triphosphate (NTP) analogues in which the γ-phosphate is covalently modified by two different biodegradable masking units and d4T as nucleoside analogue that enable the delivery of d4TTP with high selectivity in phosphate buffer (pH 7.3) and by enzyme-triggered reactions in human CD4+ T-lymphocyte CEM cell extracts. This allows the bypass of all steps normally needed

  我们公开了一项关于核苷三磷酸酯（NTP）类似物的研究，其中γ-磷酸酯被两个不同的可生物降解的掩蔽单元和d4T进行了共价修饰，从而使d4TTP在磷酸盐缓冲液（pH 7.3）和酶中具有较高的选择性CD4 + T淋巴细胞CEM细胞提取物中触发的反应。这允许绕过细胞内磷酸化通常所需的所有步骤。这些Tri PPP将包含酰氧基苄基（AB；酯）或烷氧基羰氧基苄基（ACB；碳酸酯）与ACB部分结合的环核苷酸描述为NTP递送系统。这两个不同基团的引入导致通过化学水解，特别是通过细胞提取酶选择性地形成γ-（ACB）-d4TTP。γ-（AB）-d4TTP的裂解速度比γ-（ACB）-d4TTP更快。在抗病毒测定中，这些化合物在野生型CEM / O细胞中具有更强的抗HIV-1和HIV-2活性，更重要的是在缺乏胸苷激酶的CD4 + T细胞（CEM / TK –）中具有很高的活性。