diglycolic anhydride | 119120-82-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diglycolic anhydride
• 英文别名: diglycolic acid anhydride；2,2'-{Oxybis[(2-oxoethane-2,1-diyl)oxy]}diacetic acid；2-[2-[2-(carboxymethoxy)acetyl]oxy-2-oxoethoxy]acetic acid
• CAS: 119120-82-0
• 化学式: C₈H₁₀O₉
• 分子量: 250.162
• InChiKey: KCDVQVJOZKIHNG-UHFFFAOYSA-N

物化性质

• 沸点：
  520.4±45.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  diglycolic anhydride 在 吡啶 、 氯化亚砜 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 1,4,7,10,13,16-hexaoxacyclooctadecane-2,6,11,15-tetraone
  参考文献：
  名称：

  Bogatskii, A. V.; Luk'yanenko, N. G.; Shapkin, V. A., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, # 10, p. 1750 - 1757

  摘要：

  DOI：

文献信息

• New betulinic acid derivatives as potent proteasome inhibitors
  作者：Keduo Qian、Sang-Yong Kim、Hsin-Yi Hung、Li Huang、Chin-Ho Chen、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2011.07.072

  日期：2011.10

  study, 22 new betulinic acid (BA) derivatives were synthesized and tested for their inhibition of the chymotrypsin-like activity of 20S proteasome. From the SAR study, we concluded that the C-3 and C-30 positions are the pharmacophores for increasing the proteasome inhibition effects, and larger lipophilic or aromatic side chains are favored at these positions. Among the BA derivatives tested, compounds

  在这项研究中，合成了 22 种新的桦木酸 (BA) 衍生物并测试了它们对 20S 蛋白酶体的胰凝乳蛋白酶样活性的抑制作用。从 SAR 研究中，我们得出结论，C-3 和 C-30 位置是增加蛋白酶体抑制作用的药效团，并且在这些位置有利于较大的亲脂或芳香侧链。在测试的BA衍生物，化合物13，20，和21显示出最好的蛋白酶体抑制活性，IC 50个分别1.42，1.56，和1.80μM，的值，它是三至四倍比蛋白酶体抑制控制LLM-F更有效和乳胱氨酸。
• Synthesis and proteasome inhibition of lithocholic acid derivatives
  作者：Zhao Dang、Andrew Lin、Phong Ho、Dominique Soroka、Kuo-Hsiung Lee、Li Huang、Chin-Ho Chen

  DOI：10.1016/j.bmcl.2011.02.041

  日期：2011.4

  A new class of proteasome inhibitors was synthesized using lithocholic acid as a scaffold. Modification at the C-3 position of lithocholic acid with a series of acid acyl groups yielded compounds with a range of potency on proteasome inhibition. Among them, the phenylene diacetic acid hemiester derivative (13) displayed the most potent proteasome inhibition with IC50 = 1.9 mu M. Enzyme kinetic analysis indicates that these lithocholic acid derivatives are noncompetitive inhibitors of the proteasome. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and proteasome inhibition of glycyrrhetinic acid derivatives
  作者：Li Huang、Donglei Yu、Phong Ho、Keduo Qian、Kuo-Hsiung Lee、Chin-Ho Chen

  DOI：10.1016/j.bmc.2008.05.078

  日期：2008.7

  This study discovered that glycyrrhetinic acid inhibited the human 20S proteasome at 22.3 mu M. Esterification of the C-3 hydroxyl group on glycyrrhetinic acid with various carboxylic acid reagents yielded a series of analogs with marked improved potency. Among the derivatives, glycyrrhetinic acid 3-O-isophthalate (17) was the most potent compound with IC50 of 0.22 mu M, which was approximately 100-fold more potent than glycyrrhetinic acid. (c) 2008 Elsevier Ltd. All rights reserved.
• Engel; Isaac; Posselt, Arzneimittel-Forschung/Drug Research, 1983, vol. 33, # 9, p. 1215 - 1218
  作者：Engel、Isaac、Posselt、Thiemer、Uthemann

  DOI：——

  日期：——
• JOSIMOTO, TAKEHO;IGARASI, KEHJITI;URA, MASAAKI;EHNOMOTO, YUDZI;FUNAKOSI, +
  作者：JOSIMOTO, TAKEHO、IGARASI, KEHJITI、URA, MASAAKI、EHNOMOTO, YUDZI、FUNAKOSI, +

  DOI：——

  日期：——