methyl (2β,3α,18β)-2,3-dihydroxy-11-oxo-olean-12-en-30-oate | 52154-34-4

• 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: methyl (2β,3α,18β)-2,3-dihydroxy-11-oxo-olean-12-en-30-oate
• 英文别名: 2,3-dihydroxy-glycyrrhetinic acid methyl ester；methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,11S,12aS,14bR)-10,11-dihydroxy-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: 52154-34-4
• 化学式: C₃₁H₄₈O₅
• 分子量: 500.719
• InChiKey: DZNOXPGBKVTTDI-JHJLFVGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2β,3α,18β)-2,3-dihydroxy-11-oxo-olean-12-en-30-oate 在 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (2S,3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-(methoxycarbonyl)-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-2,3-diyl bis(2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetate)
  参考文献：
  名称：

  A New Dual-Responsive Organogel Based on Uracil-Appended Glycyrrhetinic Acid

  摘要：

  A novel functional tweezer based on uracil-appended glycyrrhetinic acid with excellent gelation ability was synthesized, and the gel could transform to sol by F(-) and Hg(2+).

  DOI：

  10.1021/ol201129y
• 作为产物：
  描述：

  2,3-epoxy-glycyrrhetinic acid methyl ester 在 高氯酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以57%的产率得到methyl (2β,3α,18β)-2,3-dihydroxy-11-oxo-olean-12-en-30-oate
  参考文献：
  名称：

  Synthesis and binding ability of 1,2,3-triazole-based triterpenoid receptors for recognition of Hg2+ ion

  摘要：

  A novel type of receptors based on 1,2,3-triazole glycyrrhetinic acid derived from natural triterpenoid molecules has been synthesized via click chemistry and they showed high selectivity and affinity for Hg2+ ion by both the 1,2,3-triazole rings and aldehyde groups. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.079

文献信息

• Cytotoxic, antioxidant activities and structure activity relationship of some newly synthesized terpenoidal oxaliplatin analogs
  作者：Abd El-Galil E. Amr、Korany A. Ali、Mohamed M. Abdalla

  DOI：10.1016/j.ejmech.2008.05.024

  日期：2009.2

  (12) were newly synthesized using 2β,3α-dihydroxy-11-oxo-18β-olean-12-ene-30-oic acid (1) and 2α,2β-dihydroxy-18β-ursan-12-ene-28-oic acid (7) as starting materials. The synthesized compounds were evaluated for their cytotoxicity and antioxidant activities and were compared to Oxaliplatin® and vitamin C as positive controls. Some of the compounds exhibited better cytotoxicity and antioxidant activities

  使用2β，3α-二羟基-11-oxo-18β-olean-12-ene-30-oicacid（1）和2α，2β-dihydroxy-18β-ursan新合成了萜类草酸奥沙利铂衍生物（6）和（12）。-12-烯-28-油酸（7）为起始原料。合成的化合物为它们的细胞毒性和抗氧化活性进行了评价，并进行了比较，奥沙利铂®和维生素C作为阳性对照。与参考对照相比，某些化合物具有更好的细胞毒性和抗氧化活性。报告了合成化合物的详细合成，光谱数据，毒性（LD 50）和药理筛选。