hexyl 3β-hydroxy-11-oxo-olean-12-en-30-oate | 64845-99-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: hexyl 3β-hydroxy-11-oxo-olean-12-en-30-oate
• 英文别名: hexyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
• CAS: 64845-99-4
• 化学式: C₃₆H₅₈O₄
• 分子量: 554.854
• InChiKey: MUEBJYSGZIHPNA-KNPCULJYSA-N

物化性质

• 沸点：
  613.5±55.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  甘草次酸	enoxolone	471-53-4	C30H46O4	470.693
  (3beta,20beta)-20-羧基-11-氧代-30-去甲齐墩果-12-烯-3-基 2-O-beta-D-吡喃葡糖基-beta-D-吡喃葡糖苷酸	glycyrrizhin	103000-77-7	C42H62O16	822.945

反应信息

• 作为反应物：
  描述：

  hexyl 3β-hydroxy-11-oxo-olean-12-en-30-oate 在 calcium sulfate 、 氢氧化钾 、 silver carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 hexyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
  参考文献：
  名称：

  Synthetic studies on the relationship between anti-HIV activities and micelle forming abilities of various alkylated glycyrrhetinate diglycoside sodium sulfates and related compounds

  摘要：

  Sodium sulfates 11-14, 29-32, 35 and 37 of various alkyl glycyrrhizin and related compounds were synthesized. In vitro anti-HIV activities of the sulfates were compared to the activities of glycyrrhizin 1 in the inhibition of replications of HTLV-III and GUN-4. The activities of the sulfates were increased 11.1, 15.2, 9.1 and 5.0 times for 11-14, 100.0, 125.5, 83.3 and 11.6 times for 29-32, and 11.6 and 50.0 times for 35 and 37. From the relationship between CMC values and anti-HIV activities of the sulfates, it appeared that the sulfates exhibiting more potent antiviral activities had higher micelle forming abilities. Sodium sulfates having a triterpenoid or steroid ring in the molecule showed more potent activities than those of thioglycosides which had no such ring. From the investigation of syncytium formation, we suggest that the active sulfates inhibited HIV-1 infection early in the replication cycle of the virus.

  DOI：

  10.1016/0223-5234(96)89163-x
• 作为产物：
  描述：

  (3beta,20beta)-20-羧基-11-氧代-30-去甲齐墩果-12-烯-3-基 2-O-beta-D-吡喃葡糖基-beta-D-吡喃葡糖苷酸 在 吡啶 、 氢氧化钾 、 2-chloro-1,3-dimethyl imidazolium chloride 、 硫酸 作用下， 以 乙醇 为溶剂， 反应 29.0h， 生成 hexyl 3β-hydroxy-11-oxo-olean-12-en-30-oate
  参考文献：
  名称：

  Synthetic studies on the relationship between anti-HIV activities and micelle forming abilities of various alkylated glycyrrhetinate diglycoside sodium sulfates and related compounds

  摘要：

  Sodium sulfates 11-14, 29-32, 35 and 37 of various alkyl glycyrrhizin and related compounds were synthesized. In vitro anti-HIV activities of the sulfates were compared to the activities of glycyrrhizin 1 in the inhibition of replications of HTLV-III and GUN-4. The activities of the sulfates were increased 11.1, 15.2, 9.1 and 5.0 times for 11-14, 100.0, 125.5, 83.3 and 11.6 times for 29-32, and 11.6 and 50.0 times for 35 and 37. From the relationship between CMC values and anti-HIV activities of the sulfates, it appeared that the sulfates exhibiting more potent antiviral activities had higher micelle forming abilities. Sodium sulfates having a triterpenoid or steroid ring in the molecule showed more potent activities than those of thioglycosides which had no such ring. From the investigation of syncytium formation, we suggest that the active sulfates inhibited HIV-1 infection early in the replication cycle of the virus.

  DOI：

  10.1016/0223-5234(96)89163-x

文献信息

• Synthesis, biological evaluation and structure–activity relationships of glycyrrhetinic acid derivatives as novel anti-hepatitis B virus agents
  作者：Li-Jun Wang、Chang-An Geng、Yun-Bao Ma、Xiao-Yan Huang、Jie Luo、Hao Chen、Xue-Mei Zhang、Ji-Jun Chen

  DOI：10.1016/j.bmcl.2012.03.081

  日期：2012.5

  Fifty-seven derivatives of glycyrrhetinic acid (GA) were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated in HepG 2.2.15 cells. Among them, sixteen compounds showed greater anti-HBV activity than GA, especially, compounds 29, 32, 35, 41 exhibited significantly inhibitory activities against HBV DNA replication with IC50 values of 5.71, 5.36, 8.90 and 9.08 mu M, respectively. The structure-activity relationships (SARs) of GA derivatives were discussed for exploring novel anti-HBV agents. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthetic studies on the relationship between anti-HIV activities and micelle forming abilities of various alkylated glycyrrhetinate diglycoside sodium sulfates and related compounds
  作者：S Saito、T Furumoto、M Ochiai、A Hosono、H Hoshino、U Haraguchi、R Ikeda、N Shimada

  DOI：10.1016/0223-5234(96)89163-x

  日期：1996.1

  Sodium sulfates 11-14, 29-32, 35 and 37 of various alkyl glycyrrhizin and related compounds were synthesized. In vitro anti-HIV activities of the sulfates were compared to the activities of glycyrrhizin 1 in the inhibition of replications of HTLV-III and GUN-4. The activities of the sulfates were increased 11.1, 15.2, 9.1 and 5.0 times for 11-14, 100.0, 125.5, 83.3 and 11.6 times for 29-32, and 11.6 and 50.0 times for 35 and 37. From the relationship between CMC values and anti-HIV activities of the sulfates, it appeared that the sulfates exhibiting more potent antiviral activities had higher micelle forming abilities. Sodium sulfates having a triterpenoid or steroid ring in the molecule showed more potent activities than those of thioglycosides which had no such ring. From the investigation of syncytium formation, we suggest that the active sulfates inhibited HIV-1 infection early in the replication cycle of the virus.