胆固醇2-丙炔基-1-YL碳酸酯 | 33985-07-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 胆固醇2-丙炔基-1-YL碳酸酯
• 英文名称: cholesteryl 2-propyn-1-yl carbonate
• 英文别名: Cholest-5-en-3-ol (3beta)-, 2-propynyl carbonate；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] prop-2-ynyl carbonate
• CAS: 33985-07-8
• 化学式: C₃₁H₄₈O₃
• 分子量: 468.72
• InChiKey: LLAMZFUXJMSJTD-GTPODGLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  胆固醇2-丙炔基-1-YL碳酸酯 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 [1-(3-aminopropyl)triazol-4-yl]methyl [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] carbonate;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  ‘Click’ synthesized sterol-based cationic lipids as gene carriers, and the effect of skeletons and headgroups on gene delivery

  摘要：

  In this work, we have successfully prepared a series of new sterol-based cationic lipids (1-4) via an efficient 'Click' chemistry approach. The pDNA binding affinity of these lipids was examined by EB displacement and agarose-gel retardant assay. The average particle sizes and surface charges of the sterol-based cationic lipids/pDNA lipoplexes were analyzed by dynamic laser light scattering instrument (DLS), and the morphologies of the lipoplexes were observed by atomic force microscopy (AFM). The cytotoxicity of the lipids were examined by MTT and LDH assay, and the gene transfection efficiencies of these lipid carriers were investigated by luciferase gene transfection assay in various cell lines. In addition, the intracellular uptake and trafficking/localization behavior of the Cy3-DNA loaded lipoplexes were preliminarily studied by fluorescence microscopy. The results demonstrated that the pDNA loading capacity, lipoplex particle size, zeta potential and morphology of the sterol lipids/pDNA lipoplexes depended largely on the molecular structure factors including sterol-skeletons and headgroups. Furthermore, the sterol-based lipids showed quite different cytotoxicity and gene transfection efficacy in A549 and HeLa cells. Interestingly, it was found that the cholesterol-bearing lipids 1 and 2 showed 7-10(4) times higher transfection capability than their lithocholate-bearing counterparts 3 and 4 in A549 and HeLa cell lines, suggested that the gene transfection capacity strongly relied on the structure of sterol skeletons. Moreover, the study on the structure-activity relationships of these sterol-based cationic lipid gene carriers provided a possible approach for developing low cytotoxic and high efficient lipid gene carriers by selecting suitable sterol hydrophobes and cationic headgroups. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.047
• 作为产物：
  描述：

  胆固醇甲酰氯 、 2-丙炔-1-醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到胆固醇2-丙炔基-1-YL碳酸酯
  参考文献：
  名称：

  多功能铂（Ⅱ）联吡啶配合物的合成，表征及光致变色，发光，金属成对和液晶性质

  摘要：

  一系列多官能铂（II）的联吡啶配合物的设计，合成，和其特征在于，11 H NMR，快速原子轰击质谱（FAB-MS）和元素分析。研究了它们的电化学和光物理性质。还研究了含有螺萘并恶嗪的复合物的光致变色特性。这些配合物中的一些已显示出能够在有机溶剂中形成稳定的热可逆金属茂。与典型的热致有机凝胶和金属成对剂不同，其中一种配合物可以在十二烷中形成金属成对剂，并且对外部刺激非常稳定。通过在各种温度下的动力学研究，确定了十二烷凝胶中代表性的含有螺并萘恶嗪的配合物的漂白反应的光致变色活化参数。在其中一种配合物中还观察到层状液晶行为，

  DOI：

  10.1002/chem.201003738

文献信息

• Cholesterol-/Estradiol-Appended Alkynylplatinum(II) Complexes as Supramolecular Gelators: Synthesis, Characterization, Photophysical and Gelation Studies
  作者：Yongguang Li、Elizabeth Suk-Hang Lam、Anthony Yiu-Yan Tam、Keith Man-Chung Wong、Wai Han Lam、Lixin Wu、Vivian Wing-Wah Yam

  DOI：10.1002/chem.201301510

  日期：2013.7.22

  A series of cholesterol‐/estradiol‐appended alkynylplatinum(II) complexes with tridentate N‐donor ligands, based on 2,6‐bis(1‐alkylpyrazol‐3‐yl)pyridine, has been synthesized and characterized by 1H NMR spectroscopy, FAB‐mass spectrometry, and elemental analysis. Their photophysical properties have also been investigated. Computational studies have been performed to provide insights into the nature

  已合成了一系列基于2,6-双（1-烷基吡唑-3-基）吡啶的三齿N-供体配体的胆固醇/雌二醇附加的炔基铂（II）配合物，并通过1 H NMR光谱进行了表征， FAB质谱法和元素分析。还研究了它们的光物理性质。已经进行了计算研究，以提供有关电子过渡的本质的见解。已发现某些复合物可形成稳定的热响应和机械响应超分子凝胶。
• Luminescent Amphiphilic 2,6-Bis(1,2,3-triazol-4-yl)pyridinePlatinum(II) Complexes: Synthesis, Characterization, Electrochemical, Photophysical, and Langmuir-Blodgett Film-Formation Studies
  作者：Yongguang Li、Le Zhao、Anthony Yiu-Yan Tam、Keith Man-Chung Wong、Lixin Wu、Vivian Wing-Wah Yam

  DOI：10.1002/chem.201301788

  日期：2013.10.18

  been synthesized and characterized. Their electrochemical and photophysical properties have also been studied. Two amphiphilic platinum(II)2,6‐bis(1‐dodecyl‐1,2,3‐triazol‐4‐yl)pyridine complexes (3‐Cl and 8) were found to form stable and reproducible Langmuir–Blodgett (LB) films at the air/water interface. These LB films were characterized by the study of their surface‐pressure–molecular‐area (π–A) isotherms

  具有三齿配体2,6-双（1-烷基-1,2-，3-三唑-4-基）吡啶和2,6-双（1-芳基-1,2， 3-三唑-4-基）吡啶（N7R），[PT（N7R）CL] X（17）和[PT（N7R）（CCR'）] X（8 - 17 ; R = ñ -C 4 H 9，n C 8 H 17，n C 12 H 25，n C 14 H 29，n C 18 H 37，C 6 H 5和CH 2 C6 H 5；R'= C 6 H 5，C 6 H 4‐ CH 3 ‐ p ， C 6 H 4‐ CF 3 ‐ p，C 6 H 4‐ N（CH 3）2 ‐ p和胆固醇2‐丙炔‐1‐ p碳酸基酯 X =光学传递函数-，PF 6 -和Cl - ），已经合成和表征。还已经研究了它们的电化学和光物理性质。两种两亲性铂金（II）发现2,6-双（1-十二烷基-1,2,3-三唑-4-基）吡啶配合物（3-Cl和8）在空气/水中形成稳定且
• Supramolecular inclusion complexes of a star polymer containing cholesterol end-capped poly(ε-caprolactone) arms with β-cyclodextrin
  作者：Erdinc Doganci、Mesut Gorur、Cavit Uyanik、Faruk Yilmaz

  DOI：10.1002/pola.27408

  日期：2014.12.1

  emanating from a phosphazene core (N3P3‐(PCL‐Chol)6) was synthesized by a combination of ring‐opening polymerization and “click” chemistry techniques. For this purpose, the terminal OH groups of the synthesized precursor (N3P3‐(PCL‐OH)6) were converted into –Chol through a series of reaction. Both N3P3‐(PCL‐OH)6 and N3P3‐(PCL‐Chol)6 were then employed in the preparation of supramolecular inclusion complexes

  通过开环聚合反应合成了一种新的六臂和星形聚合物，其中包含从磷腈核（N 3 P 3-（PCL-Chol）6）发出的带有胆固醇封端的聚（ε-己内酯）臂和“点击”化学技术。为了这个目的，终端合成前体的OH基（N 3 P 3 - （PCL-OH）6）转化为-通过一系列反应的澈。N 3 P 3-（PCL-OH）6和N 3 P 3-（PCL-Chol）6然后将其用于与β-环糊精（β-CD）的超分子包合物（ICs）的制备。后者以更高的产量形成了带有β-CD的IC。N 3 P 3-（PCL-Chol）6的IC中的主宾化学计量（ε-CL：β-CD，mol：mol）为1.2。使用傅立叶变换红外光谱（FTIR）和1 H核磁共振（NMR）光谱方法，广角X射线衍射证实了具有β-CD的N 3 P 3-（PCL-Chol）6的超分子IC的形成。（WAXD）和热分析技术。WAXD数据表明，所获得的IC具有N 3 P 3
• US3935337A
  申请人：——

  公开号：US3935337A

  公开（公告）日：1976-01-27
• US4101207A
  申请人：——

  公开号：US4101207A

  公开（公告）日：1978-07-18