6-(5-cholesten-3β-yloxy)-1-iodohexane | 68354-86-9

• 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: 6-(5-cholesten-3β-yloxy)-1-iodohexane
• 英文别名: 6-(5-cholesten-3β-yloxy)hexyl iodide；cholest-5-en-3β-yl 6-iodohexyl ether；6-(5-Cholesten-3beta-yloxy)hexyl iodide；(3S,8S,9S,10R,13R,14S,17R)-3-(6-iodohexoxy)-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]phenanthrene
• CAS: 68354-86-9
• 化学式: C₃₃H₅₇IO
• 分子量: 596.719
• InChiKey: VJEDJQCHBNNRTP-IJXDZZBXSA-N

物化性质

• 沸点：
  580.1±43.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(5-cholesten-3β-yloxy)-1-iodohexane 在 sodium hydroxide 、 sodium methylate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 24.75h， 生成 cholest-5-en-3β-yl 6-<(p-carboxybenzyl)thio>hexyl ether succinimido ester
  参考文献：
  名称：

  Functional cholesteryl binding agents: synthesis, characterization, and evaluation of antibody binding to modified phospholipid vesicles

  摘要：

  A series of functionalized cholesteryl derivatives were synthesized. The various lipophilic protein modification agents were analyzed for their protein binding ability. The binding of human IgG, labeled with 125I, to modified phospholipid vesicles was ascertained. Two agents performed well. These were cholest-5-en-3 beta-yl 5-carboxypentyl ether succinimido ester and cholest-5-en-3 beta-yl 6-carboxyhexyl ether succinimido ester.

  DOI：

  10.1021/jm00160a004
• 作为产物：
  描述：

  cholest-5-en-3β-yl 6-<(p-tolylsulfonyl)oxy>hexyl ether 在 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 6-(5-cholesten-3β-yloxy)-1-iodohexane
  参考文献：
  名称：

  Steroidal glycolipids as host resistance stimulators against viral

  摘要：

  本发明涉及甾体衍生物的糖脂类化合物，其中甾体通过中等长度的碳氢链与1-硫代-D-甘露糖苷或1-硫代-L-岩藻糖苷相连，用于保护免疫功能受损的宿主，尤其是由艾滋病相关病毒引起的，免受机会性感染的侵害。

  公开号：

  US04942154A1

文献信息

• Steroidal glycolipids as host resistance stimulators
  申请人：Merck & Co., Inc.

  公开号：US04652553A1

  公开（公告）日：1987-03-24

  Described are derivatives of glycolipids with substituted steroids bridged via a medium length hydrocarbon chain to 1-thio-D-mannopyranoses or 1-thio-L-fucopyranoses. These compounds protect an immunocompromised human or animal host against opportunistic infection by virtue of their immunostimulant properties.

  描述了通过中等长度的碳氢链连接到1-硫代-D-甘霖糖或1-硫代-L-岩藻糖的替代类固醇的糖脂衍生物。这些化合物通过其免疫刺激性能保护免疫受损的人类或动物宿主免受机会性感染的侵害。
• Synthesis of 6-(5-cholesten-3β-yloxy)hexyl 4-O-(6-deoxy-β-d-galactopyranosyl)-1-thio-β-d-glucopyranoside and derivatives thereof for in vivo liposome studies
  作者：Mitree M. Ponpipom、Margaret S. Wu、James C. Robbins、T.Y. Shen

  DOI：10.1016/0008-6215(83)88034-3

  日期：1983.7

  Abstract 6-(5-Cholesten-3β-yloxy)hexyl 4- O -(6-deoxy- and 3,6-anhydro-β- d -galactopyranosyl)-1-thio-β- d -glucopyranoside were prepared from benzyl 4- O -β- d -galactopyranosyl-β- d -glucopyranoside, and incorporated into phospholipid vesicles. When injected intravenously into rats, these disaccharide-modified liposomes were found to be taken up mainly by liver cells.

  摘要用苄基4制备了6-（5-Cholesten-3β-yloxy）己基4-O-（6-脱氧和3,6-脱水-β-d-吡喃半乳糖基）-1-硫代-β-d-吡喃葡萄糖苷。 -O-β-d-吡喃半乳糖基-β-d-吡喃葡萄糖苷，并掺入磷脂囊泡中。当静脉内注射到大鼠中时，发现这些二糖修饰的脂质体主要被肝细胞吸收。
• Cell-specific glycopeptide ligands
  申请人：Merck & Co., Inc.

  公开号：US04386026A1

  公开（公告）日：1983-05-31

  Cell-specific ligands comprising conjugates of saccharides and amino acids or peptides are synthesized from amino acids such as ornithine, lysine, peptides such as dilysine, diornithine or oligolysine and selected saccharides having reactive functional groups protected by appropriate blocking groups. Such glycopeptides are useful as tissue specific substances, which when coupled with bioactive materials through metabolizable or hydrolyzable linkages, deliver such bioactive materials to the selected site. In this manner, antiinflammatory drugs such as dexamethasone are linked through a metabolizable or hydrolyzable linkage and on administration to an animal suffering from inflammatory disease carries the drug to the site of inflammation for intracellular release. Other examples include the macrophage ligand N.sup.2 -N.sup.2, N.sup.6 -Bis-[3-(.alpha.-D-mannopyranosylthio)propionyl]-6-lysyl-N.sup.6 -[3-(.alpha.-D-mannopyranosylthio)propionyl]-L-lysine, 5, which when coupled to .beta.-glucocerebrosidase, can deliver the enzyme selectively to kupffer cells. This is useful in the enzyme replacement therapy of Gaucher's disease.

  由氨基酸（如鸟氨酸，赖氨酸）、肽（如双赖氨酸、双鸟氨酸或寡赖氨酸）和选定的具有适当阻断基保护的反应性官能团的糖组成的细胞特异性配体被合成。这种糖肽可用作组织特异性物质，当通过可代谢或可水解的连接与生物活性材料耦合时，可将这些生物活性材料输送到所选的部位。通过这种方式，例如，抗炎药物如地塞米松通过可代谢或可水解的连接与之链接，并在对患有炎症性疾病的动物进行治疗时将药物带到炎症部位进行细胞内释放。其他例子包括巨噬细胞配体N.sup.2-N.sup.2，N.sup.6-Bis-[3-(.alpha.-D-mannopyranosylthio)propionyl]-6-lysyl-N.sup.6-[3-(.alpha.-D-mannopyranosylthio)propionyl]-L-lysine，5，当与β-葡聚糖酶耦合时，可以将酶有选择地输送到库普弗细胞。这在高氏病的酶替代疗法中非常有用。
• Steroidal glycolipids
  申请人：Merck & Co., Inc.

  公开号：US04652637A1

  公开（公告）日：1987-03-24

  Described are derivatives of glycolipids with substituted steroids bridged via a medium length hydrocarbon chain to 1-thio-D-mannopyranoses or 1-thio-L-fucopyranoses. These compounds protect an immunocompromised human or animal host against opportunistic infection by virtue of their immunostimulant properties.

  本文描述了一种通过介质长度的碳氢链桥接到1-硫基-D-甘露糖或1-硫基-L-岩藻糖的取代类固醇的糖脂衍生物。这些化合物具有免疫刺激性质，能够保护免疫系统受损的人或动物宿主免受机会性感染的侵害。
• Immunologic adjuvant
  申请人：Merck & Co., Inc.

  公开号：US04229441A1

  公开（公告）日：1980-10-21

  Glycolipid compounds of the formulae ##STR1## wherein R is ##STR2## are useful immunologic adjuvants in vaccines.

  公式为##STR1##其中R为##STR2##的糖脂类化合物是疫苗中有用的免疫佐剂。