6-(5-pregnen-20-on-3β-yloxy)hexyl 1-thio-β-D-mannopyranoside | 108435-15-0

• 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-pregnen-20-on-3β-yloxy)hexyl 1-thio-β-D-mannopyranoside
• 英文别名: 6-(pregn-5-en-20-one-3beta-yloxy)hexyl 1-thio-beta-D-mannopyranoside；1-[(3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-[6-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylhexoxy]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 108435-15-0
• 化学式: C₃₃H₅₄O₇S
• 分子量: 594.854
• InChiKey: IRAXAFUQXZIRLR-XCNQWDLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-(5-pregnen-20-on-3β-yloxy)hexyl 1-thio-β-D-mannopyranoside 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以61%的产率得到6-(5-pregnen-20-ol-3β-yloxy)hexyl 1-thio-β-D-mannopyranoside
  参考文献：
  名称：

  Glycolipids as host resistance stimulators

  摘要：

  6-(5-Cholesten-3 beta-yloxy)hexyl 1-thio-beta-D-mannopyranoside (L-644,257) enhances natural host resistance in cyclophosphamide-treated mice against Pseudomonas aeruginosa in a dose-dependent manner. It is active sc, im, and ip but not orally. L-644,257 is substantially more protective against P. aeruginosa than its alpha anomer. The beta-L-fucose glycolipid is more effective when given im and ip than sc. The lactose and beta-D-glucose glycolipids were only marginally effective to nonprotective. The 17 beta-steroidal side chain of L-644,257 can be modified without substantial loss of protective activity.

  DOI：

  10.1021/jm00164a062
• 作为产物：
  描述：

  6-(5-pregnen-20-on-3β-yloxy)hexyl iodide 、 sodium salt of 1-thio-α-D-mannose 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 以70%的产率得到6-(5-pregnen-20-on-3β-yloxy)hexyl 1-thio-β-D-mannopyranoside
  参考文献：
  名称：

  Glycolipids as host resistance stimulators

  摘要：

  6-(5-Cholesten-3 beta-yloxy)hexyl 1-thio-beta-D-mannopyranoside (L-644,257) enhances natural host resistance in cyclophosphamide-treated mice against Pseudomonas aeruginosa in a dose-dependent manner. It is active sc, im, and ip but not orally. L-644,257 is substantially more protective against P. aeruginosa than its alpha anomer. The beta-L-fucose glycolipid is more effective when given im and ip than sc. The lactose and beta-D-glucose glycolipids were only marginally effective to nonprotective. The 17 beta-steroidal side chain of L-644,257 can be modified without substantial loss of protective activity.

  DOI：

  10.1021/jm00164a062

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.

  描述了一种通过中等长度的碳氢链桥接到1-硫代-D-甘露糖或1-硫代-L-岩藻糖的取代类固醇的糖脂衍生物。这些化合物通过其免疫刺激性质保护免疫受损的人类或动物宿主免受机会性感染的侵害。
• 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。
• Steroidal glycolipids as host resistance stimulators against viral
  申请人：Merck & Co., Inc.

  公开号：US04942154A1

  公开（公告）日：1990-07-17

  Disclosed are steroidal derivatives of glycolipids, in which steroids are bridged, via a medium length hydrocarbon chain, to 1-thio-D-mannopyranoses or 1-thio-L-fucopyranoses that protect an immunocompromised host, particularly resulting from an AIDS-related virus, against opportunistic infection.

  本发明涉及一种糖脂的甾体衍生物，其中甾体通过中等长度的烃链与1-硫代-D-甘露糖或1-硫代-L-岩藻糖桥接，以保护免疫受损宿主（特别是由艾滋病病毒引起的）免受机会性感染的影响。