methyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-3-O-18β-glycyrrhetinate | 148529-99-1

• 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: methyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-3-O-18β-glycyrrhetinate
• 英文别名: methyl glycyrrhetinate β-lactoside；methyl glycyrrhetate β-lactoside；methyl (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
• CAS: 148529-99-1
• 化学式: C₄₃H₆₈O₁₄
• 分子量: 809.005
• InChiKey: PDWURRSPPOGXPS-NRLBTUFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  57
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  222
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-3-O-18β-glycyrrhetinate 在 pyridine-SO3 complex 作用下， 以 吡啶 为溶剂， 反应 24.0h， 生成 methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-[(2R,3R,4S,5R,6R)-3,4-disulfooxy-6-(sulfooxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trisulfooxy-6-(sulfooxymethyl)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 calcium sulfate 、 氢氧化钾 、 硫酸 、 silver carbonate 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 55.0h， 生成 methyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-3-O-18β-glycyrrhetinate
  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

• ——
  作者：Nisar Ullah、Werner Seebacher、Ernst Haslinger、Johann Jurenitsch、Katharina Rauchensteiner、Robert Weis

  DOI：10.1007/s706-002-8243-6

  日期：2002.2

   The partial synthesis of lactosides of glycyrrhetic acid, its 11-deoxo and 18α-derivatives, and their methyl esters is described. The influence of the aglycon structure on the hemolytic properties of the title compounds is discussed and compared with those of oleanolic acid derivatives. Furthermore, we describe an optimized preparation of 18α-glycyrrhetic acid.

  描述了甘草次酸，其11-脱氧和18α-衍生物及其甲基酯的乳糖苷的部分合成。糖苷配基结构对标题化合物溶血特性的影响进行了讨论，并与齐墩果酸衍生物进行了比较。此外，我们描述了18α-甘草次酸的优化制备方法。
• Structure—activity relationships of synthetic methyl glycyrrhetate glycosides
  作者：Masayuki Takechi、Yasuo Tanaka

  DOI：10.1016/s0031-9422(00)95086-6

  日期：1993.3

  Of 15 synthetic methyl glycyrrhetate glycosides, the monoglycosides having CH2OH-6 or Me-6 in their sugar moieties and the diglycosides having a (1-->4) linkage between the sugar residues showed higher haemolytic activities than the others. The beta-maltoside and beta-lactoside exhibited much stronger antifungal activities against Trichophyton mentagrophytes than the others. However, none of them exhibited antibacterial activity against Staphylococcus aureus or Bacillus subtilis.