1-azido-docosane | 66143-74-6

• 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: 1-azido-docosane
• 英文别名: 1-azidodocosane；1-docosyl azide；docosyl azide；Decosylazid；behenyl azide
• CAS: 66143-74-6
• 化学式: C₂₂H₄₅N₃
• 分子量: 351.619
• InChiKey: FQWCDICXOYZKKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  25
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-azido-docosane 在 palladium on activated charcoal 甲酸 、 氢气 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 20.0 ℃ 、427.48 kPa 条件下， 反应 12.0h， 生成 4-(2-carboxyethyl)-4-(3-docosylureido)heptanedioic acid
  参考文献：
  名称：

  Synthesis, Critical Micelle Concentrations, and Antimycobacterial Properties of Homologous, Dendritic Amphiphiles. Probing Intrinsic Activity and the “Cutoff” Effect

  摘要：

  Newkome-type, 1 -> 3 C-branched dendrons make an excellent headgroup for amphiphiles with ultralong, saturated, linear alkyl chains. Synthesis of a homologous series of five such amphiphiles from 14 to 22 carbonsRNHCONHC(CH2CH2CO2H)(3), R = n-CnH2n+1, n = 14, 16, 18, 20, 22proceeds readily. These amphiphiles are soluble in aqueous solutions of triethanolamine. Surface-tension measurements on this homologous series reveal an unusually gradual decrease in log critical micelle concentration (CMC) as the chain length increases. In fact, the tetradecyl homologue does not appear to form micelles. Further, measurements of minimal inhibitory concentration (MIC) by broth microdilution against Mycobacterium smegmatis as a function of the initial cell density provide a direct measure of the intrinsic activity (MIC0) of each homologue. The hexadecyl homologue is the most active at inhibiting growth with an MIC0 equal to 3.5 x 10(-5) M, which is 100-fold below the CMC.

  DOI：

  10.1021/jm061240d
• 作为产物：
  描述：

  二十二烷-1-醇 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-azido-docosane
  参考文献：
  名称：

  用于多价纳米级肝素结合的自组装配体

  摘要：

  超分子珍珠串：聚阳离子配体可自组装成球形假树状聚合物，能够以相似的亲和力和结合模式结合聚阴离子肝素，类似于树状聚合物和蛋白质的共价纳米结构（参见图片；紫色：肝素，红色/蓝色） ：自组装配体）。配体与肝素的结合诱导形成的纳米结构的纳米级组织。

  DOI：

  10.1002/anie.201100019

文献信息

• CHEMICAL MODIFICATIONS OF MONOMERS AND OLIGONUCLEOTIDES WITH CYCLOADDITION
  申请人：Manoharan Muthiah

  公开号：US20120035115A1

  公开（公告）日：2012-02-09

  The invention features compounds of formula I or II: In one embodiment, the invention relates compounds and processes for conjugating ligand to oligonucleotide. The invention further relates to methods for treating various disorders and diseases such as viral infections, bacterial infections, parasitic infections, cancers, allergies, autoimmune diseases, immunodeficiencies and immunosuppression.

  该发明涉及公式I或II的化合物：在一种实施方式中，该发明涉及化合物和用于将配体与寡核苷酸结合的过程。该发明进一步涉及治疗各种疾病和疾病的方法，例如病毒感染、细菌感染、寄生虫感染、癌症、过敏、自身免疫疾病、免疫缺陷和免疫抑制。
• An immobilized and reusable Cu(<scp>i</scp>) catalyst for metal ion-free conjugation of ligands to fully deprotected oligonucleotides through click reaction
  作者：Laxman Eltepu、Muthusamy Jayaraman、Kallanthottathil G. Rajeev、Muthiah Manoharan

  DOI：10.1039/c2cc36811k

  日期：——

  Chelation of Cu(I) ions to an immobilized hydrophilic tris(triazolylmethyl)amine chelator on a solid support allowed synthesis of RNA oligonucleotide conjugates from completely deprotected alkyne-oligonucleotides. No oligonucleotide strand degradation or metal ion contamination was observed. Furthermore, use of the immobilized copper(I) ion overcame regioselectivity issues associated with strain-promoted copper-free azide–alkyne cycloaddition.

  将 Cu(I)离子与固定在固体载体上的亲水性三（三氮唑甲基）胺螯合剂螯合后，可利用完全脱保护的炔寡核苷酸合成 RNA 寡核苷酸共轭物。没有观察到寡核苷酸链降解或金属离子污染。此外，固定铜（I）离子的使用克服了与应变促进无铜叠氮-炔环加成相关的区域选择性问题。
• Heparin versus DNA: Chiral Preferences in Polyanion Binding to Self-Assembled Multivalent (SAMul) Nanostructures
  作者：Stephen M. Bromfield、David K. Smith

  DOI：10.1021/jacs.5b04344

  日期：2015.8.19

  This communication presents simple cationic self-assembling multivalent (SAMul) first generation dendrons based on L or D lysine, which form identical nanoscale assemblies in terms of dimensions and charge densities but toward which DNA and heparin exhibit different chiral binding preferences. However, higher generation dendrons with larger hydrophilic head groups are bound identically by these polyanions, irrespective of chirality. We propose that well-organized chiral ligands on the surface of self-assembled nanostructures can exhibit enantioselective polyanion binding. This demonstrates that small structural changes can be amplified by self-assembly and impact on nanoscale binding.
• Betylates. 3. Preparative nucleophilic substitution by way of [2]-, [3]-, and [4]betylates. Stoichiometric phase transfer and substrate-reagent ion-pair (SRIP) reactions of betylates
  作者：J. F. King、S. M. Loosmore、M. Aslam、J. D. Lock、M. J. McGarrity

  DOI：10.1021/ja00389a038

  日期：1982.12
• Lead structures for applications in photodynamic therapy 7. Efficient synthesis of amphiphilic glycosylated lipid porphyrin derivatives: refining linker conjugation for potential PDT applications
  作者：Claire Moylan、Ayman M.K. Sweed、Yasser M. Shaker、Eoin M. Scanlan、Mathias O. Senge

  DOI：10.1016/j.tet.2015.04.097

  日期：2015.6

  Herein, we report synthetic strategies towards a library of amphiphilic tetraphenyl porphyrins anchored to synthetic saccharides and lipid modalities. The carbohydrates and lipid functionalities are covalently linked to the model photosensitizer via a copper (I) catalyzed alkyne azide cycloaddition reaction or an oxypropyl linkage achieved by nucleophilic substitution chemistry. Varying substitutions of carbohydrates and lipids allows for potential fine tuning of solubility and photophysical characteristics important for imaging and treatment applications in photomedicine, specifically in photodynamic therapy. (C) 2015 Elsevier Ltd. All rights reserved.