2-(2-羟基乙氧基)乙基癸酸酯 | 7735-31-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-(2-羟基乙氧基)乙基癸酸酯
• 英文名称: 2-(2-benzyloxyethoxy)ethyl decanoate
• 英文别名: Diethylenglykolmonocaprinat；2-(2-Hydroxyethoxy)ethyl decanoate
• CAS: 7735-31-1
• 化学式: C₁₄H₂₈O₄
• 分子量: 260.374
• InChiKey: AWQKXJYKNFMHJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  2-(2-羟基乙氧基)乙基癸酸酯 在 4-二甲氨基吡啶 、 草酰氯 、 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 3.83h， 生成 3α-{3-[2-(2-decanoyloxyethoxy)ethoxycarbonyl]propanoyloxy}-7α,12α-dihydroxy-5β-cholan-24-oic acid
  参考文献：
  名称：

  New propanoyloxy derivatives of 5β-cholan-24-oic acid as drug absorption modifiers

  摘要：

  A series of final twelve propanoyloxy derivatives of 5 beta-cholan-24-oic acid (O-propanoyl derivatives of cholic acid) as potential drug absorption modifiers (skin penetration enhancers, intestinal absorption promoters) was generated by multistep synthesis. Structure confirmation of all generated compounds was accomplished by H-1 NMR, C-13 NMR, IR and MS spectroscopy methods. All the prepared compounds were analyzed using RP-TLC, and their lipophilicity (R-M) was determined. The hydrophobicity (log P), solubility (log S), polar surface area (PSA) and molar volume (MV) of the studied compounds were also calculated. All the target compounds were tested for their in vitro transdermal. penetration effect and as potential intestinal absorption enhancers. The cytotoxicity of all the evaluated compounds was evaluated against normal human skin fibroblast cells. Their anti-proliferative activity was also assessed against human cancer cell lines: T-lymphoblastic leukemia cell line and breast adenocarcinoma cell line. One compound showed selective cytotoxicity against human skin fibroblast cells and another compound possessed the highest cytotoxicity against all the tested cell lines. Only one compound expressed anti-proliferative effect on leukemia cancer cells without affecting the growth of normal cells, which should be promising in potential development of new drugs. Most of the target compounds showed minimal anti-proliferative activity (IC50 > 37 mu M), indicating they would have moderate cytotoxicity when administered as chemical absorption modifiers. The relationships between the lipophilicity/polarity and the chemical structure of the studied compounds as well as the relationships between their chemical structure and enhancement effect are discussed in this article. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.02.001
• 作为产物：
  描述：

  2-(2-benzyloxyethoxy)ethyl decanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以76%的产率得到2-(2-羟基乙氧基)乙基癸酸酯
  参考文献：
  名称：

  New propanoyloxy derivatives of 5β-cholan-24-oic acid as drug absorption modifiers

  摘要：

  A series of final twelve propanoyloxy derivatives of 5 beta-cholan-24-oic acid (O-propanoyl derivatives of cholic acid) as potential drug absorption modifiers (skin penetration enhancers, intestinal absorption promoters) was generated by multistep synthesis. Structure confirmation of all generated compounds was accomplished by H-1 NMR, C-13 NMR, IR and MS spectroscopy methods. All the prepared compounds were analyzed using RP-TLC, and their lipophilicity (R-M) was determined. The hydrophobicity (log P), solubility (log S), polar surface area (PSA) and molar volume (MV) of the studied compounds were also calculated. All the target compounds were tested for their in vitro transdermal. penetration effect and as potential intestinal absorption enhancers. The cytotoxicity of all the evaluated compounds was evaluated against normal human skin fibroblast cells. Their anti-proliferative activity was also assessed against human cancer cell lines: T-lymphoblastic leukemia cell line and breast adenocarcinoma cell line. One compound showed selective cytotoxicity against human skin fibroblast cells and another compound possessed the highest cytotoxicity against all the tested cell lines. Only one compound expressed anti-proliferative effect on leukemia cancer cells without affecting the growth of normal cells, which should be promising in potential development of new drugs. Most of the target compounds showed minimal anti-proliferative activity (IC50 > 37 mu M), indicating they would have moderate cytotoxicity when administered as chemical absorption modifiers. The relationships between the lipophilicity/polarity and the chemical structure of the studied compounds as well as the relationships between their chemical structure and enhancement effect are discussed in this article. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.02.001

文献信息

• Cancer drug and uses
  申请人：Health Clinics Limited

  公开号：US10188668B2

  公开（公告）日：2019-01-29

  A pharmaceutical composition comprising a cancer therapeutic that is capable of inhibiting and/or reducing the ability of a cancer cell to take up and utilize glucose or other energy source, a lipid or other building block of a cell membrane or organelle, and/or cholesterol. The pharmaceutical composition can comprise one or more cancer therapeutics that can be administered individually or in combination to an individual.

  一种药物组合物，包含一种癌症治疗剂，该治疗剂能够抑制和/或降低癌细胞吸收和利用葡萄糖或其他能量源、脂质或细胞膜或细胞器的其他构件和/或胆固醇的能力。药物组合物可包含一种或多种癌症治疗剂，可单独或联合给药。
• ZEJNALOV B. K.; GARIBOV F. I.; NASIROV A. B.; KERIMOV P. M.; BAJRAMOVA M.+, UCH. ZAP. AZERB. YH-T. CEP. XIM. N., 1977, HO 2, 20-23
  作者：ZEJNALOV B. K.、 GARIBOV F. I.、 NASIROV A. B.、 KERIMOV P. M.、 BAJRAMOVA M.+

  DOI：——

  日期：——
• JPH05222083A
  申请人：——

  公开号：JPH05222083A

  公开（公告）日：1993-08-31
• Cancer Drug and Uses
  申请人：Health Clinics Limited

  公开号：US20170189425A1

  公开（公告）日：2017-07-06

  A pharmaceutical composition comprising a cancer therapeutic that is capable of inhibiting and/or reducing the ability of a cancer cell to take up and utilize glucose or other energy source, a lipid or other building block of a cell membrane or organelle, and/or cholesterol. The pharmaceutical composition can comprise one or more cancer therapeutics that can be administered individually or in combination to an individual.
• US4851282A
  申请人：——

  公开号：US4851282A

  公开（公告）日：1989-07-25