6-phthalimido-1-(5-cholesten-3β-yloxy)hexane | 79360-09-1

• 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-phthalimido-1-(5-cholesten-3β-yloxy)hexane
• 英文别名: cholest-5-en-3β-yl 6-phthalimidohexyl ether；6-Phthalimido-1-(5-cholesten-3beta-yloxy)hexane；2-[6-[[(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]oxy]hexyl]isoindole-1,3-dione
• CAS: 79360-09-1
• 化学式: C₄₁H₆₁NO₃
• 分子量: 615.94
• InChiKey: ILBGKOKZXHBEPZ-LOOOARRWSA-N

物化性质

• 沸点：
  678.5±48.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-phthalimido-1-(5-cholesten-3β-yloxy)hexane 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 cholest-5-en-3β-yl 6-aminohexyl ether
  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-hydroxyhexyl ether 在 吡啶 、 Bu₃P(CH₂)16CH₂Br 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 6-phthalimido-1-(5-cholesten-3β-yloxy)hexane
  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

文献信息

• 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。
• Cell-specific ligands for selective drug delivery to tissues and organs
  作者：Mitree M. Ponpipom、Robert L. Bugianesi、James C. Robbins、T. W. Doebber、T. Y. Shen

  DOI：10.1021/jm00144a004

  日期：1981.12

  Various numbers of D-mannose residues have been attached via spacer arms to lysine, dilysine, and oligolysine backbones. These D-mannosyl peptide analogues were found to be potent competitive inhibitors of the uptake of 125I-labeled D-mannose-bovine serum albumin conjugate by rat alveolar macrophages. The inhibitory potency of these synthetic ligands increased with increasing number of carbohydrate moieties. The chirality of the peptide backbone did not appear to play a major role in binding, whereas variations of the length and linkage of the spacer arm notably affected the inhibitory activities. The saccharide specificity of the macrophage receptor was demonstrated by the inactivity of the corresponding D-galactosyl peptide analogues. The L-fucosyl peptide derivative was only weakly active. The trimannosyldilysine ligand (KI = 3.9 microM) and its analogues are potentially useful in selective delivery of therapeutic agents to macrophages.
• Functional cholesteryl binding agents: synthesis, characterization, and evaluation of antibody binding to modified phospholipid vesicles
  作者：Timothy R. Carroll、Alan Davison、Alun G. Jones

  DOI：10.1021/jm00160a004

  日期：1986.10

  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.