cholesterylprop-2-ynylcarbamate | 942400-20-6

• 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
• 英文名称: cholesterylprop-2-ynylcarbamate
• 英文别名: cholesterylprop-2-ynylcarbamate amine；cholesteryl 2-propyn-1-yl carbamate；[(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] N-prop-2-ynylcarbamate
• CAS: 942400-20-6
• 化学式: C₃₁H₄₉NO₂
• 分子量: 467.736
• InChiKey: JHAROLDEQDANHC-GTPODGLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(5-iodoracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 、 cholesterylprop-2-ynylcarbamate 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以53%的产率得到(1R,3R,4R,7S)-3-[5-(3-cholesterylcarbonylaminopropyn-1-yl)uracil-1-yl]-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Synthesis and Biophysical Properties of C5-Functionalized LNA (Locked Nucleic Acid)

  摘要：

  Oligonucleotides modified with conformationally restricted nucleotides such as locked nucleic acid (LNA) monomers are used extensively in molecular biology and medicinal chemistry to modulate gene expression at the RNA level. Major efforts have been devoted to the design of LNA derivatives that induce even higher binding affinity and specificity, greater enzymatic stability, and more desirable pharmacokinetic profiles. Most of this work has focused on modifications of LNA's oxymethylene bridge. Here, we describe an alternative approach for modulation of the properties of LNA: i.e., through functionalization of LNA nucleobases. Twelve structurally diverse CS-functionalized LNA uridine (U) phosphoramidites were synthesized and incorporated into oligodeoxyribonucleotides (ONs), which were then characterized with respect to thermal denaturation, enzymatic stability, and fluorescence properties. ONs modified with monomers that are conjugated to small alkynes display significantly improved target affinity, binding specificity, and protection against 3'-exonucleases relative to regular LNA. In contrast, ONs modified with monomers that are conjugated to bulky hydrophobic alkynes display lower target affinity yet much greater 3'-exonuclease resistance. ONs modified with C5-fluorophore-functionalized LNA-U monomers enable fluorescent discrimination of targets with single nucleotide polymorphisms (SNPs). In concert, these properties render C5-functionalized LNA as a promising class of building blocks for RNA-targeting applications and nucleic acid diagnostics.

  DOI：

  10.1021/jo500614a
• 作为产物：
  描述：

  胆固醇甲酰氯 、 丙炔胺盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以82%的产率得到cholesterylprop-2-ynylcarbamate
  参考文献：
  名称：

  两亲性铂(Ⅱ)配合物及其制备和构筑白色发 光体系的应用

  摘要：

  本发明公开了一种两亲性铂(Ⅱ)配合物及其制备和构筑白色发光体系的应用，该配合物的结构式为：式中m为3～5的整数，n＝1或2，该两亲性铂(Ⅱ)配合物是以醚氧链为亲水部分，以胆固醇为疏水部分，其具有自组装特性，且制备方法简单，反应条件温和。本发明两亲性铂(Ⅱ)配合物在不同含水量的二甲亚砜/水混合溶剂、不同温度、不同激发波长下均发射白光，且白色发光体系的量子产率最高可达5.8％，是一种发光性能优异的铂配合物单组分白色发光材料。

  公开号：

  CN109336932B

文献信息

• Synthesis and sensing applications of a new fluorescent derivative of cholesterol
  作者：Yanchao Lü、Qingqing Sun、Baolong Hu、Xiangli Chen、Rong Miao、Yu Fang

  DOI：10.1039/c5nj02601f

  日期：——

  The Hg²⁺ quenched emission of a specially designed fluorophore could be fully turned on upon the introduction of organophosphorus pesticides.

  经过特殊设计的荧光物质的发射可以在有机磷农药引入后完全被打开。
• Cyclometalated Platinum(II) Complexes of 1,3-Bis(1-<i>n</i>-butylpyrazol-3-yl)benzenes: Synthesis, Characterization, Electrochemical, Photophysical, and Gelation Behavior Studies
  作者：Yeye Ai、Yongguang Li、Huiqing Ma、Cheng-Yong Su、Vivian Wing-Wah Yam

  DOI：10.1021/acs.inorgchem.6b02033

  日期：2016.11.21

  platinum(II) complexes of N^C^N ligands, where N^C^N = 1,3-bis(1-n-alkylpyrazol-3-yl)benzene (bpzb), namely, [Pt(bpzb)Cl] (1 and 2) and [Pt(bpzb)(C≡C–R)] (3–10) (R = C6H5, C6H4–OCH3-p, C6H4–NO2-p, C6H4–NH2-p, 4-cholesteryl phenyl carbamate, and cholesteryl methylcarbamate) were synthesized and characterized. Their electrochemical and photophysical properties were investigated. Two of the platinum(II) complexes

  N ^ C ^ N配体的一系列新的环金属化铂（II）配合物，其中N ^ C ^ N = 1,3-双（1- n-烷基吡唑-3-基）苯（bpzb），即[Pt （bpzb）Cl]（1和2）和[Pt（bpzb）（C≡C–R）]（3 – 10）（R = C 6 H 5，C 6 H 4 –OCH 3 - p，C 6 H 4 –NO 2 - p，C 6 H 4 –NH 2 - p合成并表征了4-胆固醇氨基甲酸酯苯基和胆固醇甲基甲酸酯。研究了它们的电化学和光物理性质。X射线晶体学还对其中两种铂（II）配合物进行了结构表征，并观察到了短分子间C–H···Pt接触。在溶液状态下观察到由三重态IL（3 IL）激发的bpzb配体的振动态结构，并混合了3个MLCT [dπ（Pt）→π*（bpzb）]特征。有趣的是，配合物5显示出低能量发射，其源自对硝基苯基乙炔基配体的参与。综合大楼9 发现具有疏水性胆甾醇的4-乙炔
• C5-Alkynyl-Functionalized α-L-LNA: Synthesis, Thermal Denaturation Experiments and Enzymatic Stability
  作者：Pawan Kumar、Bharat Baral、Brooke A. Anderson、Dale C. Guenther、Michael E. Østergaard、Pawan K. Sharma、Patrick J. Hrdlicka

  DOI：10.1021/jo5006153

  日期：2014.6.6

  Major efforts are currently being devoted to improving the binding affinity, target specificity, and enzymatic stability of oligonucleotides used for nucleic acid targeting applications in molecular biology, biotechnology, and medicinal chemistry. One of the most popular strategies toward this end has been to introduce additional modifications to the sugar ring of affinity-inducing conformationally restricted nucleotide building blocks such as locked nucleic acid (LNA). In the preceding article in this issue, we introduced a different strategy toward this end, i.e., C5-functionalization of LNA uridines. In the present article, we extend this strategy to alpha-L-LNA: i.e., one of the most interesting diastereomers of LNA. alpha-L-LNA uridine monomers that are conjugated to small C5-alkynyl substituents induce significant improvements in target affinity, binding specificity, and enzymatic stability relative to conventional alpha-L-LNA. The results from the back-to-back articles therefore suggest that C5-functionalization of pyrimidines is a general and synthetically straightforward approach to modulate biophysical properties of oligonucleotides modified with LNA or other conformationally restricted monomers.