2-azidoethyl n-dodecyl ether | 460343-09-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-azidoethyl n-dodecyl ether
• 英文别名: 1-(2-azidoethoxy)dodecane；1-(2-Azidoethoxyl)dodecane
• CAS: 460343-09-3
• 化学式: C₁₄H₂₉N₃O
• 分子量: 255.404
• InChiKey: WJKWVVUHUYHSLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-azidoethyl n-dodecyl ether 在 三苯基膦 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 28.17h， 以76%的产率得到2-(dodecyloxy)ethanamine
  参考文献：
  名称：

  Lipophilic amines as potent inhibitors of N-acylethanolamine-hydrolyzing acid amidase

  摘要：

  N-Acylethanolamines (NAEs) including N-arachidonoylethanolamine (anandamide) and N-palmitoylethanolamine are endogenous lipid mediators. These molecules are degraded to the corresponding fatty acids and ethanolamine by fatty acid amide hydrolase (FAAH) or NAE-hydrolyzing acid amidase (NAAA). Lipophilic amines, especially pentadecylamine (2c) and tridecyl 2-aminoacetate (11b), were found to exhibit potent NAAA inhibitory activities (IC50 = 5.7 and 11.8 mu M), with much weaker effects on FAAH. These simple structures would provide a scaffold for further improvement in NAAA inhibitory activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.065
• 作为产物：
  描述：

  乙二醇单十二烷基醚 在 咪唑 、 sodium azide 、 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 2-azidoethyl n-dodecyl ether
  参考文献：
  名称：

  Anchor Dependency for Non-Glycerol Based Cationic Lipofectins: Mixed Bag of Regular and Anomalous Transfection Profiles

  摘要：

  Although detailed structure activity, physicochemical and biophysical investigations in probing the anchor influence in liposomal gene delivery have been reported for glycerol-based transfection lipids, the corresponding investigation for non-glycerol based simple monocationic transfection lipids have not yet been undertaken. Towards this end, herein, we delineate our structure - activity and physicochemical approach in deciphering the anchor dependency in liposomal gene delivery using fifteen new structural analogues (lipids 1 - 15) of recently reported nonglycerol based monocationic transfection lipids. The C-14 analogues in both series 1 (lipids 1 - 6) and series 2 (lipids 7-15) showed maximum efficiency in transfecting COS-1 and CHO cells. However, the C-12 analogue of the ether series (lipid 3) exhibited a seemingly anomalous behavior compared with its transfection efficient C-10 and C-14 analogues (lipids 2 and 4) in being completely inefficient to transfect both COS-1 and CHO cells. The present structure - activity investigation also convincingly demonstrates that enhancement of transfection efficiencies through incorporation of membrane reorganizing unsaturation elements in the hydrophobic anchor of cationic lipids is not universal but cell dependent. The strength of the interaction of lipids 1 - 15 with DNA was assessed by their ability to exclude ethidium bromide bound to the DNA. Cationic lipids with long hydrophobic tails were found, in general, to be efficient in excluding EtBr from DNA. Gel to liquid crystalline transition temperatures of the lipids was measured by fluorescence anisotropy measurement technique. In general (lipid 2 being an exception), transfection efficient lipids were found to have their mid transition temperatures at or below physiological temperatures (37degreesC).

  DOI：

  10.1002/1521-3765(20020215)8:4<900::aid-chem900>3.0.co;2-x

文献信息

• AMINE COMPOUNDS HAVING ANTI-INFLAMMATORY, ANTIFUNGAL, ANTIPARASITIC, AND ANTICANCER ACTIVITY
  申请人：WELLSTAT THERAPEUTICS CORPORATION

  公开号：US20150361077A1

  公开（公告）日：2015-12-17

  Amine compounds having activity against inflammation, fungi, unicellular parasitic microorganisms, and cancer are described. The compounds contain a monocyclic, bicyclic, or tricyclic aromatic ring having one, two, or three ring nitrogen atoms.

  本文描述了对炎症、真菌、单细胞寄生微生物和癌症具有活性的胺化合物。这些化合物包含一个单环、双环或三环芳香环，其中含有一个、两个或三个环氮原子。
• Amine compounds having anti-inflammatory, antifungal, antiparasitic, and anticancer activity
  申请人：Wellstat Therapeutics Corporation

  公开号：US10030015B2

  公开（公告）日：2018-07-24

  Amine compounds having activity against inflammation, fungi, unicellular parasitic microorganisms, and cancer are described. The compounds contain a monocyclic, bicyclic, or tricyclic aromatic ring having one, two, or three ring nitrogen atoms.

  本文描述了具有抗炎、抗真菌、抗单细胞寄生微生物和抗癌活性的胺化合物。这些化合物含有单环、双环或三环芳香环，环上有一个、两个或三个氮原子。
• Aminoquinazoline compounds having anti-inflammatory, antifungal, antiparasitic, and anticancer activity
  申请人：Wellstat Therapeutics Corporation

  公开号：US10934284B2

  公开（公告）日：2021-03-02

  Amine compounds having activity against inflammation, fungi, unicellular parasitic microorganisms, and cancer are described. The compounds contain a monocyclic, bicyclic, or tricyclic aromatic ring having one, two, or three ring nitrogen atoms.

  本文描述了具有抗炎、抗真菌、抗单细胞寄生微生物和抗癌活性的胺化合物。这些化合物含有单环、双环或三环芳香环，环上有一个、两个或三个氮原子。
• [EN] AMINE COMPOUNDS HAVING ANTI-INFLAMMATORY, ANTIFUNGAL, ANTIPARASITIC AND ANTICANCER ACTIVITY<br/>[FR] COMPOSÉS AMINE AYANT UNE ACTIVITÉ ANTI-INFLAMMATOIRE, ANTIFONGIQUE, ANTIPARASITAIRE ET ANTICANCÉREUSE
  申请人：WELLSTAT THERAPEUTICS CORP

  公开号：WO2014120995A3

  公开（公告）日：2014-10-16
• AMINE COMPOUNDS HAVING ANTI-INFLAMMATORY, ANTIFUNGAL, ANTIPARASITIC AND ANTICANCER ACTIVITY
  申请人：Wellstat Therapeutics Corporation

  公开号：EP2950649B1

  公开（公告）日：2020-03-04