3-β-tosyloxy-Δ⁵-cholestene | 197704-36-2

• 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: 3-β-tosyloxy-Δ⁵-cholestene
• 英文别名: (8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 4-methylbenzenesulfonate；3-beta-Hydroxy-5-cholestene 3-tosylate；[(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] 4-methylbenzenesulfonate
• CAS: 197704-36-2
• 化学式: C₃₄H₅₂O₃S
• 分子量: 540.851
• InChiKey: RNZDACWUXZHQMI-PCHCLZCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-β-tosyloxy-Δ⁵-cholestene 在 四丁基硫酸氢铵 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Design, synthesis and evaluation of liposomes modified with dendritic aspartic acid for bone-specific targeting

  摘要：

  Bone diseases are notoriously difficult diseases to treat due to the comparatively low blood flows in bone tissue. Therefore, targeting delivery of drugs to bone may not only enhance the treatment efficacy, but also reduce the quantity of drug administered. In order to increase the distribution of paclitaxel (PTX) in bone, in this study, a series of novel dendritic aspartic acid derivatives were designed and synthesized as liposome ligands to deliver PTX to bone effectively. The liposomes were prepared by thin film hydration method and its particle size, zeta potential, encapsulation efficiency, release profile, stability, hemolysis were also characterized. All the aspartic acid-coated liposomes showed more than 60% binding rates to hydroxyapatite (HAP), especially the PTX-Asp(8)-Lip exhibited dramatic binding rates (> 97%) after 24 h. Moreover, the bone-targeting study in vivo indicated that all liposomes could improve the accumulation of PTX in bone, among which, the PTX-Asp(8)-Lip showed the best affinity due to the increase of aspartic acid residues exposed on the liposome surface. These results provided a novel and effective entry to the development of bone-targeting drugs.

  DOI：

  10.1016/j.chemphyslip.2019.104832
• 作为产物：
  描述：

  胆甾-5-烯-3-醇 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 8.0h， 生成 3-β-tosyloxy-Δ⁵-cholestene
  参考文献：
  名称：

  Synthesis of Multivalent Glucosides with High Affinity for GLUT1 Transporter

  摘要：

  本研究合成了新型双功能化合物 L1 和 L2，它们以团苷作为脑靶向脂质体的配体。以 2-苯基-1,3-二氧杂环戊烷-5-醇（8）和四蒽醇（13）为核心支架，通过三甘醇链连接胆固醇衍生物，而它们的其余分支则与两个或三个苄基葡萄糖苷连接，之后再进行脱苯反应，生成二蒽葡萄糖苷配体 L1 和三蒽葡萄糖苷配体 L2。这种设计为合成的双功能化合物穿越血脑屏障（BBB）提供了一个有效的入口。

  DOI：

  10.2174/157017812801322390

文献信息

• STEROLS MODIFIED BY POLYETHYLENE GLYCOL, THE PREPARATION AND THE USE THEREOF
  申请人：Zhang Wenfang

  公开号：US20100036140A1

  公开（公告）日：2010-02-11

  The invention provides sterols modified by polyethylene glycol represented by the following formula, the preparation and the use thereof, wherein each symbol is defined as in the description.

  这项发明提供了由以下公式表示的聚乙二醇修饰的甾醇，以及其制备和使用，其中每个符号的定义如描述中所述。
• LIPIDS, LIPID COMPOSITIONS, AND METHODS OF USING THEM
  申请人：BARYZA Jeremy

  公开号：US20110200582A1

  公开（公告）日：2011-08-18

  Disclosed are formulation and optimization protocols for delivery of therapeutically effective amounts of biologically active agents to liver, tumors, and/or other cells or tissues. Also provided are compositions and uses for cationic lipid compounds of formula (I). The invention also relates to compositions and uses for stealth lipids of formula (XI). Also provided are processes for making such compounds, compositions, and formulations, plus methods and uses of such compounds, compositions, and formulations to deliver biologically active agents to cells and/or tissues.

  本文披露了用于将生物活性剂量有效传递至肝脏、肿瘤和/或其他细胞或组织的配方和优化方案。还提供了具有化学式（I）的阳离子脂质化合物的组成和用途。该发明还涉及具有化学式（XI）的隐身脂质的组成和用途。还提供了制备这种化合物、组成物和配方的方法，以及利用这些化合物、组成物和配方将生物活性剂传递至细胞和/或组织的方法和用途。
• Synthetic mimics of mammalian cell surface receptors: method and compositions
  申请人：Peterson R. Blake

  公开号：US20060229235A1

  公开（公告）日：2006-10-12

  The present invention relates to new synthetic receptors. More particularly, the present invention relates to the use of the synthetic receptors for delivering a protein, peptide, drug, prodrug, lipid, nucleic acid, carbohydrate or small molecule into a target cell via receptor-mediated endocytosis. According to the invention, novel synthetic mimics of cell surface receptors have been designed and methods for use of the same are disclosed.

  本发明涉及新的合成受体。更具体地，本发明涉及利用合成受体通过受体介导的内吞作用将蛋白质、肽、药物、前药、脂质、核酸、碳水化合物或小分子输送到靶细胞中。根据本发明，已设计了细胞表面受体的新型合成模拟物，并公开了其使用方法。
• Synthesis and liquid crystal behavior of new side chain aliphatic polycarbonates based on cholesterol
  作者：Xiaofeng Liu、Zhihao Guo、Yujiao Xie、Zhangpei Chen、Jianshe Hu、Liqun Yang

  DOI：10.1016/j.molliq.2018.03.060

  日期：2018.6

  series of new liquid crystal aliphatic block polycarbonates copolymers mPEG43-b-P(MCC-Cn)51 (n = 1–4) via the ring-opening polymerization, hydrogenation reduction and coupling reaction, which contained side functionalized cholesteryl groups and were different in the number of the flexible methylene groups. The chemical structures of the chiral compounds and copolymers obtained in this study were characterized

  在这项研究中，我们 通过开环聚合，加氢还原和偶联反应，合成了一系列新型的液晶脂族嵌段聚碳酸酯共聚物mPEG 43 - b -P（MCC-C n）51（n = 1-4）。含有侧官能化的胆固醇基，并且柔性亚甲基的数目不同。本研究获得的手性化合物和共聚物的化学结构通过FT-IR和1通过平均分子量凝胶渗透色谱法（GPC）研究1 H NMR谱和共聚物的平均分子量。偏光光学显微镜（POM），差示扫描量热法（DSC）和X射线衍射（XRD）用于表征液晶行为。讨论了手性化合物和共聚物的结构和相行为受间隔物长度影响的关系。结果，具有两个亚甲基的手性化合物仅表现出近晶A（SmA）相，而具有更多亚甲基的那些手性化合物则表现出SmA和胆甾相。随着柔性亚甲基数目的增加，相应的熔融温度，LC相的转变温度和手性化合物的各向同性温度均呈下降趋势，中间相的温度范围变窄。具有两种亚甲基的聚碳酸酯共聚物没有显示出同晶型，而具有更
• Lipophilic Polynucleotide Conjugates
  申请人：Vagle Kurt

  公开号：US20120128761A1

  公开（公告）日：2012-05-24

  Disclosed are lipophilic polynucleotide conjugates including polynucleotide-cholesterol conjugates and methods of delivering therapeutic polynucleotides to a mammalian cell or patient in need of treatment using said conjugates. The disclosure further provides methods of synthesizing the lipophilic polynucleotide conjugates. The conjugates are designed to mimic or target cellular miRNAs. The lipophilic moiety, such as cholesterol or cholesterol derivative, is spaced from the polynucleotide by a substantially linear hydrocarbon group. Due to an absence of significantly polar groups and/or exchangeable protons in the vicinity of the lipophilic moiety, the interaction between the lipophilic moiety and cell membranes is enhanced to provide for efficient entry into cells.

  揭示了包括疏水性多核苷酸共轭物在内的多核苷酸-胆固醇共轭物，并提供了使用这些共轭物将治疗性多核苷酸输送到需要治疗的哺乳动物细胞或患者的方法。该公开还提供了合成疏水性多核苷酸共轭物的方法。这些共轭物被设计成模拟或靶向细胞miRNAs。疏水性基团，如胆固醇或胆固醇衍生物，通过一个基本线性的烃基与多核苷酸分开。由于在疏水性基团周围缺乏明显的极性基团和/或可交换的质子，疏水性基团与细胞膜之间的相互作用增强，以提供有效进入细胞的能力。