(3β,18β,20β)-3-amino-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester | 1207976-43-9

• 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: (3β,18β,20β)-3-amino-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester
• 英文别名: (3S,18R,20S)-3-amino-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester；benzhydryl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-amino-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: 1207976-43-9
• 化学式: C₄₃H₅₇NO₃
• 分子量: 635.93
• InChiKey: CZQYFCGOKWXLID-URSBUWNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  47
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3β,18β,20β)-3-amino-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester 在 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (3β,18β,20β)-3-N-{2-[methyl (2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosyl)uronate]ethylacetylamino}-3-deoxy-11-oxo-olean-12-en-29-oic acid
  参考文献：
  名称：

  甘草甜素的间隔物连接的 1-硫代葡萄糖醛酸类似物的合成和抗病毒活性。

  摘要：

  流感病毒感染仍然是对公共健康的重大威胁，对现有药物的抗病毒耐药性的增加产生了对新的抗病毒化合物的迫切需求。从天然的、具有抗病毒活性的化合物甘草甜素开始，产生了具有改进的抗甲型流感病毒感染的抗病毒活性的间隔桥衍生物。通过用 2-碘乙基 1-硫代-β-对甘草次酸的 3-氨基和 3-硫代衍生物进行烷基化，以良好的收率制备了含有 1-硫代-β-D-葡糖醛酸残基的三萜皂苷甘草甜素的简化类似物。 D-吡喃葡萄糖苷酸衍生物。间隔连接的 3-氨基衍生物进一步转化为 N-乙酰化和 N-琥珀酰化衍生物。含有这些羧酸附属物的脱保护化合物模拟了甘草甜素的糖子部分以及甘草次酸的半琥珀酸酯衍生物，苯氧酮。在基于甲型流感病毒感染细胞的生物试验中确定了化合物的抗病毒活性，其中 3-(2-硫乙基)-N-乙酰氨基-和 3-(2-硫乙基)-硫连接的葡萄糖醛酸衍生物是有效的IC(50) 值低至 54 microM 的抑制剂。

  DOI：

  10.3762/bjoc.8.79
• 作为产物：
  描述：

  (18β,20β)-3-(hydroxyimino)-11-oxoolean-12-en-29-oic acid diphenylmethyl ester 在 titanium(III) chloride 、 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 为溶剂， 以54%的产率得到(3β,18β,20β)-3-amino-11-oxo-olean-12-en-29-oic acid diphenylmethyl ester
  参考文献：
  名称：

  Synthesis of glycyrrhetinic acid derivatives for the treatment of metabolic diseases

  摘要：

  The effect of glycyrrhetinic acid (GA) and GA-derivatives towards 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) was investigated. Novel compounds with modi. cations at positions C-3, C-11 and C-29 of the GA skeleton were prepared. Single crystal X-ray diffraction data of selected substances are reported and discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.036

文献信息

• Synthesis of glycyrrhetinic acid derivatives for the treatment of metabolic diseases
  作者：Igor Beseda、Laszlo Czollner、Priti S. Shah、Rupesh Khunt、Rawindra Gaware、Paul Kosma、Christian Stanetty、Maria Carmen del Ruiz-Ruiz、Hassan Amer、Kurt Mereiter、Thierry Da Cunha、Alex Odermatt、Dirk Claßen-Houben、Ulrich Jordis

  DOI：10.1016/j.bmc.2009.10.036

  日期：2010.1

  The effect of glycyrrhetinic acid (GA) and GA-derivatives towards 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) was investigated. Novel compounds with modi. cations at positions C-3, C-11 and C-29 of the GA skeleton were prepared. Single crystal X-ray diffraction data of selected substances are reported and discussed. (C) 2009 Elsevier Ltd. All rights reserved.
• [EN] ANTIVIRAL TRITERPENE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRITERPÈNE ANTIVIRAUX
  申请人：SAVIRA PHARMACEUTICALS GMBH

  公开号：WO2010139692A3

  公开（公告）日：2011-03-10
• Synthesis of novel 3-amino and 29-hydroxamic acid derivatives of glycyrrhetinic acid as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors
  作者：Christian Stanetty、Laszlo Czollner、Iris Koller、Priti Shah、Rawindra Gaware、Thierry Da Cunha、Alex Odermatt、Ulrich Jordis、Paul Kosma、Dirk Claßen-Houben

  DOI：10.1016/j.bmc.2010.08.046

  日期：2010.11

  Glycyrrhetinic acid, the metabolite of the natural product glycyrrhizin, is a well known nonselective inhibitor of 11 beta-hydroxysteroid dehydrogenase (11 beta-HSD) type 1 and type 2. Whereas inhibition of 11 beta-HSD1 is currently under consideration for treatment of metabolic diseases, such as obesity and diabetes, 11 beta-HSD2 inhibitors may find therapeutic applications in chronic inflammatory diseases and certain forms of cancer. So far, no selective 11 beta-HSD2 inhibitor has been developed and neither animal studies nor clinical trials have been reported based on 11 beta-HSD2 inhibition. Starting from the lead compound glycyrrhetinic acid, novel triterpene type derivatives were synthesized and analyzed for their biological activity against overexpressed human 11 beta-HSD1 and 11 beta-HSD2 in cell lysates. Several hydroxamic acid derivatives showed high selectivity for 11 beta-HSD2. The most potent and selective compound is active against human 11 beta-HSD2 in the low nanomolar range with a 350-fold selectivity over human 11 beta-HSD1. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and antiviral activities of spacer-linked 1-thioglucuronide analogues of glycyrrhizin
  作者：Christian Stanetty、Andrea Wolkerstorfer、Hassan Amer、Andreas Hofinger、Ulrich Jordis、Dirk Claßen-Houben、Paul Kosma

  DOI：10.3762/bjoc.8.79

  日期：——

  spacer-connected 3-amino derivatives were further transformed into N-acetylated and N-succinylated derivatives. The deprotected compounds containing these carboxylic acid appendices mimic the glycon part of glycyrrhizin as well as the hemisuccinate derivative of glycyrrhetinic acid, carbenoxolone. Antiviral activities of the compounds were determined in a biological test based on influenza A virus-infected

  流感病毒感染仍然是对公共健康的重大威胁，对现有药物的抗病毒耐药性的增加产生了对新的抗病毒化合物的迫切需求。从天然的、具有抗病毒活性的化合物甘草甜素开始，产生了具有改进的抗甲型流感病毒感染的抗病毒活性的间隔桥衍生物。通过用 2-碘乙基 1-硫代-β-对甘草次酸的 3-氨基和 3-硫代衍生物进行烷基化，以良好的收率制备了含有 1-硫代-β-D-葡糖醛酸残基的三萜皂苷甘草甜素的简化类似物。 D-吡喃葡萄糖苷酸衍生物。间隔连接的 3-氨基衍生物进一步转化为 N-乙酰化和 N-琥珀酰化衍生物。含有这些羧酸附属物的脱保护化合物模拟了甘草甜素的糖子部分以及甘草次酸的半琥珀酸酯衍生物，苯氧酮。在基于甲型流感病毒感染细胞的生物试验中确定了化合物的抗病毒活性，其中 3-(2-硫乙基)-N-乙酰氨基-和 3-(2-硫乙基)-硫连接的葡萄糖醛酸衍生物是有效的IC(50) 值低至 54 microM 的抑制剂。