carbonic acid ethyl ester 4-(2-hydroxy-ethyl)-phenyl ester | 1119076-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: carbonic acid ethyl ester 4-(2-hydroxy-ethyl)-phenyl ester
• 英文别名: Ethyl [4-(2-hydroxyethyl)phenyl] carbonate；ethyl [4-(2-hydroxyethyl)phenyl] carbonate
• CAS: 1119076-06-0
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: CMSYCKGAIBGQGB-UHFFFAOYSA-N

物化性质

• 沸点：
  335.3±34.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  carbonic acid ethyl ester 4-(2-hydroxy-ethyl)-phenyl ester 在 4-二甲氨基吡啶 、 硝酸 、 C.I.酸性橙108 作用下， 以 乙醇 、 二氯甲烷 、 乙酸酐 为溶剂， 反应 29.0h， 生成 21-fusidic acid (4-nitroxyethyl) phenyl ester
  参考文献：
  名称：

  发现和合成3-和21-取代的夫西地酸衍生物，作为P-糖蛋白介导的多药耐药性的逆转剂。

  摘要：

  在这项研究中，我们合成了23种夫西地酸（FA）衍生物，并根据MTT分析筛选了它们对KBV（多药耐药口腔表皮样癌）细胞系的肿瘤耐药逆转活性和细胞毒性。首次发现了夫西地酸（FA）衍生物的抗肿瘤逆转活性。我们的结果表明，化合物1以5μM的浓度增强了紫杉醇对耐药KBV细胞的细胞毒性。化合物1使KBV细胞对紫杉醇敏感，使其停滞在G2 / M期并诱导细胞凋亡。进一步的研究表明，化合物1通过增加P-gp的ATPase活性来抑制P-糖蛋白（P-gp）的药物外排活性，而不影响其表达。还初步研究了FA衍生物的构效关系（SAR）。我们的发现表明，化合物1是用于设计未来具有改善的肿瘤耐药性逆转活性的FA衍生物的有前途的先导化合物。

  DOI：

  10.1016/j.ejmech.2019.111668
• 作为产物：
  描述：

  对羟基苯乙醇 、 氯甲酸乙酯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 6.0h， 以83.3%的产率得到carbonic acid ethyl ester 4-(2-hydroxy-ethyl)-phenyl ester
  参考文献：
  名称：

  发现和合成3-和21-取代的夫西地酸衍生物，作为P-糖蛋白介导的多药耐药性的逆转剂。

  摘要：

  在这项研究中，我们合成了23种夫西地酸（FA）衍生物，并根据MTT分析筛选了它们对KBV（多药耐药口腔表皮样癌）细胞系的肿瘤耐药逆转活性和细胞毒性。首次发现了夫西地酸（FA）衍生物的抗肿瘤逆转活性。我们的结果表明，化合物1以5μM的浓度增强了紫杉醇对耐药KBV细胞的细胞毒性。化合物1使KBV细胞对紫杉醇敏感，使其停滞在G2 / M期并诱导细胞凋亡。进一步的研究表明，化合物1通过增加P-gp的ATPase活性来抑制P-糖蛋白（P-gp）的药物外排活性，而不影响其表达。还初步研究了FA衍生物的构效关系（SAR）。我们的发现表明，化合物1是用于设计未来具有改善的肿瘤耐药性逆转活性的FA衍生物的有前途的先导化合物。

  DOI：

  10.1016/j.ejmech.2019.111668

文献信息

• Design, synthesis and biological evaluation of novel α-hederagenin derivatives with anticancer activity
  作者：Xian-xuan Liu、Yan-ting Yang、Xiao Wang、Kai-yi Wang、Jia-qi Liu、Lei Lei、Xiao-min Luo、Rong Zhai、Feng-hua Fu、Hong-bo Wang、Yi Bi

  DOI：10.1016/j.ejmech.2017.09.016

  日期：2017.12

  potent cytotoxic agent than the parent compound α-hederagenin (H), 24 α-hederagenin derivatives (5–8, 11–24, 27–28, 31–32, and 35–36) were synthesized in a concise and efficient strategy and screened for in vitro cytotoxicity against the human cancer cell lines MKN45 and KB. Among these compounds, the polyamine derivative 15 exhibited more potency than the parent compound with IC50 values in the range

  在试图在比母体化合物α-常春配基的更有效的细胞毒性剂（到达ħ），24 α -hederagenin衍生物（5 - 8，11 - 24，27 - 28，31 - 32，和35 - 36）为以简洁有效的策略合成了该化合物，并筛选了针对人类癌细胞系MKN45和KB的体外细胞毒性。在这些化合物中，多胺衍生物15的效能比具有IC 50的母体化合物更高值在4.22 μM–8.05μM的范围内。化合物15增加了Bax / bcl-2的比率，从而破坏了线粒体的电位并诱导了细胞凋亡。因此，本研究强调了α-角豆生成素的多胺衍生物在新型抗癌剂的发现和开发中的重要性。
• Design, synthesis, nitric oxide release and antibacterial evaluation of novel nitrated ocotillol-type derivatives
  作者：Yi Bi、Xiao Yang、Tingting Zhang、Zeyun Liu、Xiaochen Zhang、Jing Lu、Keguang Cheng、Jinyi Xu、Hongbo Wang、Guangyao Lv、Peter John Lewis、Qingguo Meng、Cong Ma

  DOI：10.1016/j.ejmech.2015.06.021

  日期：2015.8

  Nitric oxide (NO) and its auto-oxidation products are known to disrupt normal bacterial function and NO releasing molecules have the potential to be developed as antibacterial leads in drug discovery. We have designed and synthesized a series of novel nitrated compounds by combining NO releasing groups with ocotillol-type triterpenoids, which have previously demonstrated activity only against Gram-positive bacteria. The in vitro NO release capacity and antibacterial activity were sequentially evaluated and the data showed that most of the synthesized compounds could release nitric oxide. Compound 16a, 17a and 17c, with nitrated aliphatic esters at C-3 position, displayed higher NO release than other analogues, correlating to their good antibacterial activity, in which 17c demonstrated broad-spectrum activity against both Gram positive and -negative bacteria, as well as excellent synergism at sub-minimum inhibitory concentration when using with kanamycin and chloramphenicol. Furthermore, the epifluorescent microscopic study indicated that the ocotillol-type triterpenoid core may induce NO release on the bacterial membrane. Our results demonstrate that nitrated substitutions at C-3 of ocotillol-type derivatives could provide an approach to expand their antibacterial spectrum, and that ocotillol-type triterpenoids may also be developed as appropriate carriers for NO donors in antibacterial agent discovery with low cytotoxicity. (C) 2015 Elsevier Masson SAS. All rights reserved.
• 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.
• Discovery and synthesis of 3- and 21-substituted fusidic acid derivatives as reversal agents of P-glycoprotein-mediated multidrug resistance
  作者：Mengqi Guo、Qianwen Ren、Binghua Wang、Wentao Ji、Jingxuan Ni、Yaqi Feng、Yi Bi、Jingwei Tian、Hongbo Wang

  DOI：10.1016/j.ejmech.2019.111668

  日期：2019.11

  In this study, we synthesized 23 fusidic acid (FA) derivatives and screened them for tumor drug resistance reversal activity and cytotoxicity toward the KBV (multidrug-resistant oral epidermoid carcinoma) cell line based on MTT assay. Tumor resistance reversal activity of fusidic acid (FA) derivatives was discovered for the first time. Our results showed that compound 1 enhanced the cytotoxicity of

  在这项研究中，我们合成了23种夫西地酸（FA）衍生物，并根据MTT分析筛选了它们对KBV（多药耐药口腔表皮样癌）细胞系的肿瘤耐药逆转活性和细胞毒性。首次发现了夫西地酸（FA）衍生物的抗肿瘤逆转活性。我们的结果表明，化合物1以5μM的浓度增强了紫杉醇对耐药KBV细胞的细胞毒性。化合物1使KBV细胞对紫杉醇敏感，使其停滞在G2 / M期并诱导细胞凋亡。进一步的研究表明，化合物1通过增加P-gp的ATPase活性来抑制P-糖蛋白（P-gp）的药物外排活性，而不影响其表达。还初步研究了FA衍生物的构效关系（SAR）。我们的发现表明，化合物1是用于设计未来具有改善的肿瘤耐药性逆转活性的FA衍生物的有前途的先导化合物。