1-cetyl-4-aza-1-azonia bicyclo[2.2.2]octane chloride | 62634-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-cetyl-4-aza-1-azonia bicyclo[2.2.2]octane chloride
• 英文别名: 1-Hexadecyl-1,4-diazabicyclo[2.2.2]octan-1-ium chloride；1-hexadecyl-4-aza-1-azoniabicyclo[2.2.2]octane;chloride
• CAS: 62634-15-5
• 化学式: C₂₂H₄₅N₂*Cl
• 分子量: 373.066
• InChiKey: AURPJXIGAQCDQQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-二溴戊烷 、 1-cetyl-4-aza-1-azonia bicyclo[2.2.2]octane chloride 以 甲醇 为溶剂， 反应 144.0h， 以73%的产率得到1,5-bis-(4-hexadecyl-1,4-diazoniabicyclo[2.2.2]octan-1-yl)pentane dichloride dibromide
  参考文献：
  名称：

  新型1,4-二氮杂双环[2.2.2]辛烷衍生物作为强效抗菌剂的合成及构效关系

  摘要：

  合成了一系列新的1,4-二氮杂双环[2.2.2]辛烷季铵衍生物，并评估了在不同接种量下对革兰氏阳性和革兰氏阴性细菌的几种菌株以及一种真菌的活性。测试了针对六种微生物的最小抑菌浓度（MIC）和最小杀菌浓度（MBC）。结果表明，在1,4-二氮杂双环[2.2.2]辛烷叔胺位点的取代烷基链长度与抗菌活性之间存在明确的结构-活性关系。对于化合物4a - 4k，发现MIC随着烷基链长从乙基到十二烷基的增加而降低，然后在更高的链长处增加（n> 14）。发现化合物的MIC值低4f和4g烷基链的长度为10至12个碳原子（1.6μg/ ml），与参考药物环丙沙星相当。另外，进行了时间杀灭试验以检验杀菌动力学。结果表明4f和4g对金黄色葡萄球菌具有快速杀灭作用，并在10 h g / ml的浓度下于2.5 h内消除了100％的初始细菌接种物。此外，化合物4g消除了Ps初始接种物的99.9％以上。铜绿假单胞菌经过2

  DOI：

  10.1016/j.ejmech.2015.03.033
• 作为产物：
  描述：

  三乙烯二胺 、 氯代十六烷 以 丙酮 为溶剂， 反应 48.0h， 生成 1-cetyl-4-aza-1-azonia bicyclo[2.2.2]octane chloride
  参考文献：
  名称：

  新型1,4-二氮杂双环[2.2.2]辛烷衍生物作为强效抗菌剂的合成及构效关系

  摘要：

  合成了一系列新的1,4-二氮杂双环[2.2.2]辛烷季铵衍生物，并评估了在不同接种量下对革兰氏阳性和革兰氏阴性细菌的几种菌株以及一种真菌的活性。测试了针对六种微生物的最小抑菌浓度（MIC）和最小杀菌浓度（MBC）。结果表明，在1,4-二氮杂双环[2.2.2]辛烷叔胺位点的取代烷基链长度与抗菌活性之间存在明确的结构-活性关系。对于化合物4a - 4k，发现MIC随着烷基链长从乙基到十二烷基的增加而降低，然后在更高的链长处增加（n> 14）。发现化合物的MIC值低4f和4g烷基链的长度为10至12个碳原子（1.6μg/ ml），与参考药物环丙沙星相当。另外，进行了时间杀灭试验以检验杀菌动力学。结果表明4f和4g对金黄色葡萄球菌具有快速杀灭作用，并在10 h g / ml的浓度下于2.5 h内消除了100％的初始细菌接种物。此外，化合物4g消除了Ps初始接种物的99.9％以上。铜绿假单胞菌经过2

  DOI：

  10.1016/j.ejmech.2015.03.033
• 作为试剂：
  描述：

  1,6-二溴己烷 在 1-cetyl-4-aza-1-azonia bicyclo[2.2.2]octane chloride 、 potassium iodide 作用下， 以 氯仿 、 水 为溶剂， 反应 24.0h， 以41%的产率得到1,6-二碘己烷
  参考文献：
  名称：

  Applications of surfactant-modified clays to synthetic organic chemistry

  摘要：

  Two triphase catalysts (SLL) have been developed for organic phase-aqueous phase reactions catalyzed by Suitable modified clay (solid phase). These triphase catalysts have been applied to nucleophilic displacement on activated (benzylic) as well as unactivated organic halides and provide a convenient and effective method of preparation of the corresponding products. Other useful transformations to. which these triphase catalysts have been successfully applied are the synthesis of 9,9-dichloro bicyclo[6,1,0]nonane, O-alkylation and C-alkylation of beta-naphthol. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.087

文献信息

• Polycationic Glycosides
  作者：Robert Engel、Ishrat Ghani、Diego Montenegro、Marie Thomas、Barbara Klaritch-Vrana、Alejandra Castaño、Laura Friedman、Jay Leb、Leah Rothman、Heidi Lee、Craig Capodiferro、Daniel Ambinder、Eva Cere、Christopher Awad、Faiza Sheikh、JaimeLee Rizzo、Lisa-Marie Nisbett、Erika Testani、Karin Melkonian

  DOI：10.3390/molecules16021508

  日期：——

  Cationic lipids have long been known to serve as antibacterial and antifungal agents. Prior efforts with attachment of cationic lipids to carbohydrate-based surfaces have suggested the possibility that carbohydrate-attached cationic lipids might serve as antibacterial and antifungal pharmaceutical agents. Toward the understanding of this possibility, we have synthesized several series of cationic lipids attached to a variety of glycosides with the intent of generating antimicrobial agents that would meet the requirement for serving as a pharmaceutical agent, specifically that the agent be effective at a very low concentration as well as being biodegradable within the organism being treated. The initial results of our approach to this goal are presented.

  阳离子脂质早已被认为具有抗菌和抗真菌的作用。此前将阳离子脂质附着到碳水化合物基表面的研究表明，碳水化合物附着的阳离子脂质可能作为抗菌和抗真菌药物。为了理解这种可能性，我们合成了几系列与各种糖苷相连的阳离子脂质，旨在开发符合药物要求的抗微生物剂，特别是要求在非常低的浓度下有效，并且在被治疗的生物体内可降解。我们针对这一目标的初步结果已被呈现。
• Antimicrobial surfaces
  申请人：Engel Robert

  公开号：US20050181006A1

  公开（公告）日：2005-08-18

  These and other objectives will be apparent to those having ordinary skill in the art have been achieved by providing an antimicrobial surface having formula 1: SS—(U a —V +b1 —W) b2 dX −e formula 1 wherein: SS represents a modified solid surface that comprises a hydroxyl group in the unmodified state thereof; a represents 0 or 1; U represents —Y 1 T-; Y 1 represents —O—, —S—, or —NQ-; Q represents H; a saturated or unsaturated hydrocarbon group having 1-24 atoms; phenyl; or benzyl; T represents a saturated or unsaturated hydrocarbon chain having 1-24 atoms; V represents a positively charged moiety; b1 represents 1 or 2; b2 represents 1-3; W represents LZ; L represents a saturated or unsaturated hydrocarbon chain having 10-24 atoms; Z represents —H, —OH, —SH, —F, —Cl, —Br, —I, —OR, —HN(O)CQ, or —O(O)CQ; R represents a saturated or unsaturated hydrocarbon group having 1-24 carbon atoms; phenyl; or benzyl; X represents an anion; d represents 1 or 2; and e represents 1-3; wherein b1×b2=d×e.

  这些目标以及其他目标可以被具有普通技能的人所理解，通过提供具有公式1的抗菌表面来实现：SS—（Ua—V+b1—W）b2dX−e公式1，其中：SS代表一种改性固体表面，在未改性状态下包含一个羟基；a代表0或1；U代表—Y1T-；Y1代表—O—、—S—或—NQ-；Q代表H；一个饱和或不饱和的碳氢基团，具有1-24个原子；苯基；或苄基；T代表一个饱和或不饱和的碳氢链，具有1-24个原子；V代表一个带正电的基团；b1代表1或2；b2代表1-3；W代表LZ；L代表一个饱和或不饱和的碳氢链，具有10-24个原子；Z代表—H、—OH、—SH、—F、—Cl、—Br、—I、—OR、—HN（O）CQ或—O（O）CQ；R代表一个饱和或不饱和的碳氢基团，具有1-24个碳原子；苯基；或苄基；X代表一个阴离子；d代表1或2；e代表1-3；其中b1×b2=d×e。
• Polycations. 17. Synthesis and properties of polycationic derivatives of carbohydrates
  作者：Marie Thomas、Diego Montenegro、Alejandra Castaño、Laura Friedman、Jay Leb、Mia Lace Huang、Leah Rothman、Heidi Lee、Craig Capodiferro、Daniel Ambinder、Eva Cere、Jessica Galante、JaimeLee Rizzo、Karin Melkonian、Robert Engel

  DOI：10.1016/j.carres.2009.04.021

  日期：2009.9

  In our continuing investigation of polycationic salts for purposes of antimicrobial action, ion-channel blocking, and construction of ionic liquids, we have prepared several series of polycationic salts derived from carbohydrate precursors. These salts are currently being investigated for optimal efficacy as antibacterials and antifungals, as well as for other applications. The syntheses of such series of salts are described here along with preliminary antibacterial testing results and a discussion of their properties indicating their potential utility for several purposes. (C) 2009 Elsevier Ltd. All rights reserved.
• Polycations. 18. The synthesis of polycationic lipid materials based on the diamine 1,4-diazabicyclo[2.2.2]octane
  作者：Robert Engel、JaimeLee Iolani Rizzo、Christina Rivera、Mariah Ramirez、Mia Lace Huang、Diego Montenegro、Craig Copodiferro、Valbona Behaj、Marie Thomas、Barbara Klaritch-vrana、Jeanne Fabian Engel

  DOI：10.1016/j.chemphyslip.2008.12.003

  日期：2009.3

  Herein is reported the preparation of several series of polyammonium salts that serve as cationic lipids or precursors thereof, and are structurally based on the parent diamine 1,4-diazabicyclo[2.2.2]octane (dabco).Through selective alkylation of dabco a variety of di-and tetracationic lipid species and precursors thereof have been prepared. The resultant materials are of significant interest for a variety of purposes, including serving as antimicrobial agents and antihydrophobic species, the details of which are provided in separate reports. (c) 2008 Elsevier Ireland Ltd. All rights reserved.
• ANTIMICROBIAL SURFACES
  申请人：Research Foundation of the City University of New York

  公开号：EP1496823A2

  公开（公告）日：2005-01-19