2-bromoethyl n-hexadecyl ether | 132336-43-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromoethyl n-hexadecyl ether
• 英文别名: hexadecyloxyethyl bromide；1-(2-bromoethoxy)hexadecane；1-bromo-2-hexadecyloxyethane
• CAS: 132336-43-7
• 化学式: C₁₈H₃₇BrO
• 分子量: 349.395
• InChiKey: FHMISNKPZDVHHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  20
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromoethyl n-hexadecyl ether 在 sodium hydroxide 、 sodium azide 、 水 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 134.0h， 生成 N,N-di[2-n-hexadecyloxyethyl]-N,N-di[2-hydroxyethyl]ammonium chloride
  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
• 作为产物：
  描述：

  α-氢化-ω-羟基异十六烷醇聚(氧-1,2-乙烷二基) 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以84%的产率得到2-bromoethyl n-hexadecyl ether
  参考文献：
  名称：

  [EN] TRANSTHYRETIN (TTR) IRNA COMPOSITIONS AND METHODS OF USE THEREOF FOR TREATING OR PREVENTING TTR-ASSOCIATED OCULAR DISEASES
  [FR] COMPOSITION D'ARNI DE LA TRANSTHYRÉTINE (TTR) ET SES PROCÉDÉS D'UTILISATION POUR LE TRAITEMENT OU LA PRÉVENTION DE MALADIES OCULAIRES ASSOCIÉES À TTR

  摘要：

  公开号：

  WO2021092145A8

文献信息

• PHOSPHONATE COMPOUNDS
  申请人：——

  公开号：US20040019232A1

  公开（公告）日：2004-01-29

  The present invention relates to phosphonate compounds, compositions containing them, processes for obtaining them, and their use for treating a variety of medical disorders, e.g., osteoporosis and other disorders of bone metabolism, cancer, viral infections, and the like.

  本发明涉及膦酸酯化合物、含有它们的组合物、获取它们的方法，以及它们用于治疗各种医学疾病，例如骨质疏松症和其他骨代谢紊乱、癌症、病毒感染等的用途。
• Azacytosine Derivatives Useful as Antiviral Agents
  申请人：Holy Antonin

  公开号：US20090005346A1

  公开（公告）日：2009-01-01

  The present invention provides 5-azacytosine derivatives with antiviral activity, specifically having viral replication inhibiting properties, more particularly in DNA viruses such as pox-, papilloma- and herpes viruses in humans. The invention also provides pharmaceutical compositions comprising such 5-azacytosine derivatives as active ingredients in combination with pharmaceutically acceptable carriers, which are useful for the treatment of subjects suffering from viral infections.

  本发明提供了具有抗病毒活性的5-氮杂胞嘧啶衍生物，特别是具有病毒复制抑制性质，更具体地针对DNA病毒，例如人类痘病毒、乳头瘤病毒和疱疹病毒。本发明还提供了药物组合物，其中包括这种5-氮杂胞嘧啶衍生物作为活性成分与药用载体结合，可用于治疗患有病毒感染的个体。
• Synthesis of Ester Prodrugs of 9-(<i>S</i>)-[3-Hydroxy-2-(phosphonomethoxy)propyl]-2,6-diaminopurine (HPMPDAP) as Anti-Poxvirus Agents
  作者：Marcela Krečmerová、Antonín Holý、Graciela Andrei、Karel Pomeisl、Tomáš Tichý、Petra Břehová、Milena Masojídková、Martin Dračínský、Radek Pohl、Genevieve Laflamme、Lieve Naesens、Hon Hui、Tomas Cihlar、Johan Neyts、Erik De Clercq、Jan Balzarini、Robert Snoeck

  DOI：10.1021/jm901828c

  日期：2010.10.14

  9-(S)-3-Hydroxy-2-(phosphonomethoxy)propyl]-2,6-diaminopurine (HPMPDAP) and its cyclic form were selected for further evaluation as potential drug candidates against poxvirus infections. To increase bioavailability of these compounds, synthesis of their structurally diverse ester prodrugs was carried out: alkoxyalkyl (hexadecyloxypropyl, octadecyloxyethyl, hexadecyloxyethyl), pivaloyloxymethyl (POM), 2,2,2-trifluoroethyl, butylsalicylyl, and prodrugs based on peptidomimetics. Most HPMPDAP prodrugs were synthesized in the form of monoesters is well as the corresponding cyclic phosphonate esters. The activity was evaluated not only against vaccinia virus hut also against different herpes viruses. The most potent and active prodrugs against vaccinia virus were the alkoxyalkyl ester derivatives of HPMPDAP, with 50% effective concentrations 400-600-fold lower than those of the parent compound. Prodrugs based on peptidomimetics, the 2,2,2-trifluoroethyl, the POM, and the butylsalicylyl derivatives, were able to inhibit vaccinia virus replication at 50% effective concentrations that were equivalent or similar to 10-fold lower than those observed for the parent compounds.
• WO2007/65231
  申请人：——

  公开号：——

  公开（公告）日：——
• Ester Prodrugs of Cyclic 1-(<i>S</i>)- [3-Hydroxy-2-(phosphonomethoxy)propyl]-5-azacytosine:  Synthesis and Antiviral Activity
  作者：Marcela Krečmerová、Antonín Holý、Radek Pohl、Milena Masojídková、Graciela Andrei、Lieve Naesens、Johan Neyts、Jan Balzarini、Erik De Clercq、Robert Snoeck

  DOI：10.1021/jm0707166

  日期：2007.11.1

  Reaction of 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-azacytosine (1) with dicyclohexylcarbodiimide and N,N,-dicyclohexyl-4-morpholinocarboxamidine in dimethylformamide at elevated temperature afforded the corresponding cyclic phosphonate 2, that is, 1-[(5S)-2-hydroxy-2-oxido-1,4,2-dioxaphosphinan.-5-yl]methyl}-5-azacytosine. Compound 2 exerts strong in vitro activity against DNA viruses, comparable with activity of parent compound 1. Transformation of 2 to its tetrabutylammonium salt followed by reaction with alkyl or acyloxyalkyl halogenides enabled us to prepare a series of structurally diverse ester prodrugs: alkyl (octadecyl), alkenyl (erucyl), alkoxyalkyl (hexadecyloxyethyl), and acyloxyalkyl. (pivaloyloxyrrtethyl) (3-6). The introduction of an alkyl, alkoxyalkyl, or acyloxyalkyl ester group to the molecule resulted in an increase of antiviral activity; the most active compound was found to be the hexadecyloxyethyl ester a. The relative configuration of the diastereoisomer trans-6 was determined using H,H-NOESY NMR.