22-azido-3β-(tetrahydropyran-2-yloxy)-23,24-bisnorchol-5-ene | 959126-34-2

• 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: 22-azido-3β-(tetrahydropyran-2-yloxy)-23,24-bisnorchol-5-ene
• 英文别名: 22-azido-3β-tetrahydropyranyloxy-23-bisnorchol-5-en；2-[[(3S,8S,9S,10R,13S,14S,17R)-17-[(2S)-1-azidopropan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane
• CAS: 959126-34-2
• 化学式: C₂₇H₄₃N₃O₂
• 分子量: 441.657
• InChiKey: RPBPFDLYIFROCX-GHMQSXNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  22-azido-3β-(tetrahydropyran-2-yloxy)-23,24-bisnorchol-5-ene 、 在 copper(l) iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以59%的产率得到
  参考文献：
  名称：

  FREE CHOLESTEROL ANALOGS BEARING A BORON DIPYRROMETHENE DIFLUORO (BODIPY) FLUOROPHORE IN THE SIDE CHAIN AND METHOD OF PREPARATION AND USE THEREOF

  摘要：

  本发明涉及带有硼二吡咯甲烷二氟（BODIPY）荧光团的游离胆固醇类似物及其制备方法。本发明的化合物可用于荧光光谱学和荧光显微镜技术，以可视化活细胞之间游离胆固醇的交换、分布和转运，并监测游离胆固醇在膜中有序和无序脂质域之间的运动。

  公开号：

  US20080177059A1
• 作为产物：
  描述：

  2-[[(3S,8S,9S,10R,13S,14S,17R)-17-[(2S)-1-bromopropan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane 在 sodium azide 、 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以85%的产率得到22-azido-3β-(tetrahydropyran-2-yloxy)-23,24-bisnorchol-5-ene
  参考文献：
  名称：

  FREE CHOLESTEROL ANALOGS BEARING A BORON DIPYRROMETHENE DIFLUORO (BODIPY) FLUOROPHORE IN THE SIDE CHAIN AND METHOD OF PREPARATION AND USE THEREOF

  摘要：

  本发明涉及带有硼二吡咯甲烷二氟（BODIPY）荧光团的游离胆固醇类似物及其制备方法。本发明的化合物可用于荧光光谱学和荧光显微镜技术，以可视化活细胞之间游离胆固醇的交换、分布和转运，并监测游离胆固醇在膜中有序和无序脂质域之间的运动。

  公开号：

  US20080177059A1

文献信息

• BBB-PASSING LIPID LIGAND OF HETERO NUCLEIC ACID
  申请人：National University Corporation Tokyo Medical and Dental University

  公开号：EP3770257A1

  公开（公告）日：2021-01-27

  The object of the present invention is to provide a nucleic acid agent that can be efficiently delivered to the nervous system, particularly the central nervous system to which the BBB mechanism prevents drug delivery, and can produce an antisense effect on a target transcriptional product at the delivered site, and a composition comprising the same. Provided is a double-stranded nucleic acid complex formed by annealing a first nucleic acid strand capable of hybridizing to part of a target transcriptional product, and has an antisense effect on the target transcriptional product, to a second nucleic acid strand comprising a base sequence complementary to the first nucleic acid strand, and is bound to tocopherol or an analog thereof, cholesterol or an analog thereof, or a substituted or unsubstituted C1-30 alkyl group, a substituted or unsubstituted C2-30 alkenyl group, or a substituted or unsubstituted C1-30 alkoxy group.

  本发明的目的是提供一种核酸制剂，它可以有效地递送到神经系统，特别是BBB机制阻碍药物递送的中枢神经系统，并能在递送部位对靶转录产物产生反义效应，以及包含该制剂的组合物。 本发明提供了一种双链核酸复合物，该复合物通过将能够与目标转录产物的一部分杂交的第一核酸链与包含与第一核酸链互补的碱基序列的第二核酸链退火形成，并对目标转录产物具有反义作用、并与生育酚或其类似物、胆固醇或其类似物、或取代或未取代的 C1-30 烷基、取代或未取代的 C2-30 烯基、或取代或未取代的 C1-30 烷氧基结合。
• Synthesis and Spectral Properties of Cholesterol- and FTY720-Containing Boron Dipyrromethene Dyes
  作者：Zaiguo Li、Robert Bittman

  DOI：10.1021/jo701475q

  日期：2007.10.1

  Two analogues (1, 2) of free cholesterol and one analogue (3) of the immunosuppressive sphingolipid FrY720 containing a boron dipyrromethene chromophore (BODIPY) were synthesized. The synthetic routes involved preparation of boron dipyrromethene moieties (5, 11), bearing a phenylethynyl group at different positions of the chromophore, and lipids (13, 20) bearing an azido group. The dye was tethered to the lipid via a 1,2,3-triazole in the linker by the click reaction. Analogues derived from 11 [in which an (E)-styrylethynyl moiety is bonded to C-5 of BODIPY] exhibited a marked red shift (similar to 70-80 nm) compared with those derived from 5 (in which a phenylethynyl moiety is bonded to C-8 of BODIPY).