2,3-secoporrigenin | 189014-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 2,3-secoporrigenin
• 英文别名: 2-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,14S,18R)-5',7,9,13-tetramethyl-16-oxospiro[5,17-dioxapentacyclo[10.7.0.02,9.04,8.014,18]nonadecane-6,2'-oxane]-13-yl]acetic acid
• CAS: 189014-46-8
• 化学式: C₂₇H₄₀O₆
• 分子量: 460.611
• InChiKey: OTCSBULKTTUVHL-XXSKBKDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 2,3-secoporrigenin 以 乙醚 为溶剂， 以0.8 mg的产率得到
  参考文献：
  名称：

  12-Keto-porrigenin and the unique 2,3-seco-porrigenin, new antiproliferative sapogenins from Allium porrum

  摘要：

  Two new sapogenins, 12-keto-porrigenin (1a) and 2,3-seco-porrigenin (2a), have been isolated from the organic extract of Allium porrum and identified as (25R)-5 alpha-spirostan-3 beta, 6 beta-diol-12-one (1a) and (25R)-5 alpha-2,3-secospirostan-2,3-dioic acid-6 beta-hydroxy-3,6-gamma-lactone (2a), the latter based on a unique 2,3-seco-spirostane skeleton. Small amounts of the 25S epimers, 1b and 2b, have been also found in the extract. Chemical structures were elucidated by a detailed spectroscopic analysis. In addition, 1a and 2a exhibited antiproliferative activity on four tumor cell lines in vitro. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00062-8

文献信息

• Carbohydrate–steroid conjugation by Ugi reaction: one-pot synthesis of triple sugar/pseudo-peptide/spirostane hybrids
  作者：Daniel G. Rivera、Karell Pérez-Labrada、Liudmila Lambert、Simon Dörner、Bernhard Westermann、Ludger A. Wessjohann

  DOI：10.1016/j.carres.2012.05.003

  日期：2012.10

  pseudo-peptide, and steroidal moieties is described. For this, a new carbohydrate-steroid conjugation approach based on the Ugi four-component reaction was implemented for the ligation of glucose and chacotriose to spirostanic steroids. The approach proved wide substrate scope, as both mono and oligosaccharides functionalized with amino, carboxy, and isocyano groups were conjugated to steroidal substrates in

  描述了结合糖，假肽和甾体部分的新型分子嵌合体的一锅法合成。为此，实施了基于Ugi四组分反应的新的碳水化合物-类固醇结合方法，用于将葡萄糖和二十碳三糖连接到螺甾体类固醇。该方法证明了广泛的底物范围，因为被氨基，羧基和异氰基官能化的单糖和寡糖均以有效的多组分方式与甾体底物缀合。基于Ugi反应的azo酸变体的两种替代策略被用于合成类似于天然螺旋螺皂甙的基于四唑的Chacotriose-diosgenin共轭物。这是第一次生产三糖/假肽/类固醇杂种，
• 12-Keto-porrigenin and the unique 2,3-seco-porrigenin, new antiproliferative sapogenins from Allium porrum
  作者：Alfonso Carotenuto、Ernesto Fattorusso、Virginia Lanzotti、Silvana Magno、Rosa Carnuccio、Fulvio D'Acquisto

  DOI：10.1016/s0040-4020(97)00062-8

  日期：1997.3

  Two new sapogenins, 12-keto-porrigenin (1a) and 2,3-seco-porrigenin (2a), have been isolated from the organic extract of Allium porrum and identified as (25R)-5 alpha-spirostan-3 beta, 6 beta-diol-12-one (1a) and (25R)-5 alpha-2,3-secospirostan-2,3-dioic acid-6 beta-hydroxy-3,6-gamma-lactone (2a), the latter based on a unique 2,3-seco-spirostane skeleton. Small amounts of the 25S epimers, 1b and 2b, have been also found in the extract. Chemical structures were elucidated by a detailed spectroscopic analysis. In addition, 1a and 2a exhibited antiproliferative activity on four tumor cell lines in vitro. (C) 1997 Elsevier Science Ltd.