2-(tert-butyloxycarbonylamino)-eicosanoic acid | 129850-64-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(tert-butyloxycarbonylamino)-eicosanoic acid
• 英文别名: 2-(Tert-butoxycarbonylamino)icosanoic acid；2-[(2-methylpropan-2-yl)oxycarbonylamino]icosanoic acid
• CAS: 129850-64-2
• 化学式: C₂₅H₄₉NO₄
• 分子量: 427.668
• InChiKey: OWQLVVQIZTYTOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  30
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(tert-butyloxycarbonylamino)-eicosanoic acid 在 甲醇 、 sodium hydroxide 、 tributylcosanoyl ammonium sulphate 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 2-[2-[(2-Methylpropan-2-yl)oxycarbonylamino]icosanoylamino]icosanoic acid
  参考文献：
  名称：

  Gibbons, William A.; Hughes, Richard A.; Charalambous, Mario, Liebigs Annalen der Chemie, 1990, # 12, p. 1175 - 1183

  摘要：

  DOI：
• 作为产物：
  描述：

  硬脂基溴 在 盐酸 、 sodium hydroxide 、 sodium ethanolate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 2-(tert-butyloxycarbonylamino)-eicosanoic acid
  参考文献：
  名称：

  Gibbons, William A.; Hughes, Richard A.; Charalambous, Mario, Liebigs Annalen der Chemie, 1990, # 12, p. 1175 - 1183

  摘要：

  DOI：

文献信息

• Semisynthetic derivatives of quassin
  作者：Caroline C. Lang'at、Robert A. Watt、Istvan Toth、J.David Phillipson

  DOI：10.1016/s0040-4020(98)00367-6

  日期：1998.6

  The natural product quassin has been modified in order to produce compounds with potential antimalarial action. The modifications include demethylation, reduction of the keto function, esterification with simple organic acids and- to enhance the uptake through the biological barriers and increase the stability of the compounds - with lipoamino acids.

  已对天然产物quassin进行了修饰，以生产具有潜在抗疟疾作用的化合物。修饰包括脱甲基，降低酮的功能，用简单的有机酸进行酯化，以及-通过脂氨基酸增强通过生物屏障的摄取并提高化合物的稳定性。
• Synthetic bicyclic analogues of quassinoids
  作者：Caroline C. Lang'at、Robert A. Watt、Istvan Toth、J.David Phillipson

  DOI：10.1016/s0040-4020(98)00368-8

  日期：1998.6

  A series of simple bicyclic analogues of quassinoids have been prepared including compounds with ring A typical of bruceolides and dehydrobruceolides. The synthesis of bicyclic compound 5 and tricyclic analogue 6 was accomplished by acid catalysed Robinson Annelation reaction. Hydroxyketone 9a and its 2-substituted analogues were also prepared to study the structure activity relationship.

  已经制备了一系列简单的类quassinoids双环类似物，包括具有典型的苯丁酸内酯和脱氢溴化内酯的环A的化合物。双环化合物5和三环类似物6的合成是通过酸催化的鲁宾逊退火反应完成的。还制备了羟基酮9a及其2-取代的类似物以研究结构活性关系。
• Lipidic Peptides. Ill: Lipidic Amino Acid and Oligomer Conjugates of Morphine
  作者：R.A. Hughes、I. Toth、P. Ward、S.J. Ireland、W.A. Gibbons

  DOI：10.1002/jps.2600801202

  日期：1991.12

  A series of lipidic morphine esters 1b-1f with enhanced membrane-like character were synthesized by coupling the lipidic amino acids 2a-2e to the phenolic hydroxyl group of the opioid analgesic morphine (1a). The antinocioceptive activity of the esters 1b-1f was determined in vivo following both iv and oral dosing. After iv administration, four of the conjugates, 1b, 1c, 1d, and 1f, exhibited antinocioceptive

  通过将脂质氨基酸2a-2e与阿片类镇痛吗啡（1a）的酚羟基偶联，合成了一系列具有增强的膜样特性的脂质吗啡酯1b-1f。在静脉内和口服给药后，在体内确定了酯1b-1f的抗伤害感受活性。静脉内给药后，四种缀合物1b，1c，1d和1f在小鼠腹部收缩试验中显示出抗伤害感受活性，其效力与母体化合物1a相似。结合物1b在口服给药后表现出活性。
• 2-Aminohydroxamic acid derivatives as inhibitors of Bacillus cereus phosphatidylcholine preferred phospholipase C PC-PLCBc
  作者：Patricia González-Bulnes、Albert González-Roura、Daniel Canals、Antonio Delgado、Josefina Casas、Amadeu Llebaria

  DOI：10.1016/j.bmc.2010.10.031

  日期：2010.12

  Phosphatidylcholine preferring phospholipase C (PC-PLC) is an important enzyme that plays a key role in a variety of cellular events and lipid homoeostases. Bacillus cereus phospholipase C (PC-PLCBc) has antigenic similarity with the elusive mammalian PC-PLC, which has not thus far been isolated and purified. Therefore the discovery of inhibitors of PC-PLCBc is of current interest. Here, we describe the synthesis and biological evaluation of a new type of compounds inhibiting PC-PLCBc. These compounds have been designed by evolution of previously described 2-aminohydroxamic acid PC-PLCBc inhibitors that block the enzyme by coordination of the zinc active site atoms present in PC-PLCBc [Gonzalez-Roura, A.; Navarro, I.; Delgado, A.; Llebaria, A.; Casas, J. Angew. Chem. Int. Ed. 2004, 43, 862]. The new compounds maintain the zinc coordinating groups and possess an extra trimethylammonium function, linked to the hydroxyamide nitrogen by an alkyl chain, which is expected to mimic the trimethylammonium group of the phosphatidylcholine PC-PLCBc substrates. Some of the compounds described inhibit the enzyme with IC50's in the low micromolar range. Unexpectedly, the most potent inhibitors found are those that possess a trimethylammonium group but have chemically blocked the zinc coordinating functionalities. The results obtained suggest that PC-PLCBc inhibition is not due to the interaction of compounds with the phospholipase catalytic zinc atoms, but rather results from the inhibitor cationic group recognition by the PC-PLCBc amino acids involved in choline lipid binding. (C) 2010 Elsevier Ltd. All rights reserved.
• GIBBONS, WILLIAM ANTHONY
  作者：GIBBONS, WILLIAM ANTHONY

  DOI：——

  日期：——