3O-Tosyl-18β-glycyrrhetinsaeuremethylester | 5999-11-1

• 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: 3O-Tosyl-18β-glycyrrhetinsaeuremethylester
• 英文别名: Glycyrrhetinsaeuremethylester-3β-p-toluolsulfonat；3-(4-methylbenzenesulfonate)-glycyrrhetinic acid methyl ester；methyl (3β)-3-([(4-methylphenyl)sulfonyl]oxy)-11-oxo-olean-12-en-30-oate；methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-2,4a,6a,6b,9,9,12a-heptamethyl-10-(4-methylphenyl)sulfonyloxy-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
• CAS: 5999-11-1
• 化学式: C₃₈H₅₄O₆S
• 分子量: 638.909
• InChiKey: MJGJSJRUNMUOLH-XALYGZPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  45
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  95.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3O-Tosyl-18β-glycyrrhetinsaeuremethylester 在 lithium carbonate 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-Desoxy-2.3-didehydro-18β-glycyrrhetinsaeuremethylester
  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
• 作为产物：
  描述：

  甘草次酸 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3O-Tosyl-18β-glycyrrhetinsaeuremethylester
  参考文献：
  名称：

  Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives

  摘要：

  Triterpenoic acids show many pharmacological effects, among them an antiinflammatory or an antitumor activity. One of these, glycyrrhetinic acid (1) is of interest because of its antitumor profile. Glycyrrhetinic acid is not only cytotoxic but also triggers apoptosis in various human tumor cell lines. To improve the cytotoxicity of parent 1 we set out to synthesize new derivatives of it-differing in structure and lipophilicity. These compounds were tested in a sulforhodamine B assay for cytotoxicity, and screened for their ability to induce apoptosis using an acridine orange/ethidium bromide assay and trypan blue staining. The most active compound, 34, a benzyl glycyrrhetinate holding an extra 3-N-(3-aminopropyl)glycyl substituent showed IC50 between 1.96 and 5.14 mu m for five human cancer cell lines and triggers apoptosis in 80% of the cells. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.038

文献信息

• Dehydration and solvolysis products from glycyrrhetic acid
  作者：M.H.A. Elgamal、M.B.E. Fayez

  DOI：10.1016/s0040-4020(01)82561-8

  日期：1967.1

  Dehydration of methyl glycyrrhetate (VI) and β-amyrin with PCl5 and with Fuller's earth afforded ring-A contracted products in which double bond migrations may occur. HI-induced dehydration of VI afforded a conjugated enonene 18α derivative. Solvolysis of VI sulphonate esters under a variety of conditions gave a number of ring-A contracted and uncontracted products in which the new ethenoid linkage

  用PCl 5和富勒氏土将甘草次酸甲酯（VI）和β-锚蛋白脱水，可得到双环迁移的A环缩合产物。HI诱导的VI脱水得到共轭烯烯18α衍生物。VI磺酸酯在各种条件下的溶剂化产生了许多A环收缩和未收缩的产物，其中新的类固醇连接主要限于A环。
• Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives
  作者：René Csuk、Stefan Schwarz、Bianka Siewert、Ralph Kluge、Dieter Ströhl

  DOI：10.1016/j.ejmech.2011.08.038

  日期：2011.11

  Triterpenoic acids show many pharmacological effects, among them an antiinflammatory or an antitumor activity. One of these, glycyrrhetinic acid (1) is of interest because of its antitumor profile. Glycyrrhetinic acid is not only cytotoxic but also triggers apoptosis in various human tumor cell lines. To improve the cytotoxicity of parent 1 we set out to synthesize new derivatives of it-differing in structure and lipophilicity. These compounds were tested in a sulforhodamine B assay for cytotoxicity, and screened for their ability to induce apoptosis using an acridine orange/ethidium bromide assay and trypan blue staining. The most active compound, 34, a benzyl glycyrrhetinate holding an extra 3-N-(3-aminopropyl)glycyl substituent showed IC50 between 1.96 and 5.14 mu m for five human cancer cell lines and triggers apoptosis in 80% of the cells. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis and binding ability of 1,2,3-triazole-based triterpenoid receptors for recognition of Hg2+ ion
  作者：Jun Hu、Meng Zhang、Li B. Yu、Yong Ju

  DOI：10.1016/j.bmcl.2010.06.079

  日期：2010.8

  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.