N-formyldioncophylline A

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-formyldioncophylline A
• 英文别名: (1R,3R)-7-(4,5-dimethoxy-2-methylnaphthalen-1-yl)-8-hydroxy-1,3-dimethyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde
• 化学式: C₂₅H₂₇NO₄
• 分子量: 405.494
• InChiKey: FIKWMZVLJVKJSU-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-formyldioncophylline A 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 8-O-benzyldioncophylline A
  参考文献：
  名称：

  Dioncophylline A as a Growth-Retarding Agent against the Herbivorous Insect Spodoptera littoralis:  Structure−Activity Relationships

  摘要：

  Dioncophylline A (1) represents a novel insecticidal agent, as documented by its enhanced growth-retarding effect on larvae of the polyphagous pest insect Spodoptera littoralis. Within the scope of the work described here, the potential of this as yet most active naphthylisoquinoline alkaloid was further elucidated by the preparation and testing of selected analogues. Investigation of a broad series of structurally modified dioncophylline A analogues (2-20) revealed the free amine function to be essential for the growth inhibitory effect, whereas a modification of the OH function partially led to a distinct increase of activity. In particular, the 8-O-alkyl (especially 8-O-benzylated) derivatives (14 and 15 as well as 16-19) displayed pronounced effects. In the case of 8-O-(p-bromobenzyl)dioncophylline A (16), the activity of the natural parent compound dioncophylline A (1) (EC50 = 277 mu g/g fresh wt of diet; concentration that inhibits larval growth by 50%) was even improved by a factor of >15 (EC50 = 15.6 mu g/g fresh wt).

  DOI：

  10.1021/np960707s
• 作为产物：
  描述：

  dioncophylline A 、 甲酸 以77%的产率得到
  参考文献：
  名称：

  BRINGMANN, GERHARD;RUBENACKER, MARTIN;VOGT, PETER;BUSSE, HOLGER;AKE, ASSI+, PHYTOCHEMISTRY, 30,(1991) N, C. 1691-1696

  摘要：

  DOI：

文献信息

• 5′-O-demethyl-8-O-methyl-7-epi-dioncophylline a and its ‘regularly’ configurated atropisomer from Triphyophyllum peltatum
  作者：Gerhard Bringmann、Martin Rübenacker、Wolfgang Koch、Dagmar Koppler、Thomas Ortmann、Manuela Schäffer、Laurent Aké Assi

  DOI：10.1016/s0031-9422(00)90491-6

  日期：1994.7

  The isolation and structure elucidation of two new minor naphthylisoquinoline alkaloids from the stem bark of Triphyophyllum peltatum is described. From extended spectroscopic investigations, mainly NMR and CD spectroscopy, one of the alkaloids is deduced to be 5'-O-demethyl-8-O-methyl-7-epi-dioncophylline A. This new natural product is, thus, the first dioncophylline A analogous naphthylisoquinoline alkaloid from T. peltatum with an opposite configuration at the biaryl axis. Moreover, low amounts of an additional new alkaloid were isolated, whose spectral data suggest 5'-O-demethyl-8-O-methyl-dioncophylline A, i.e. the corresponding 'normal' atropodiastereomer.
• Dioncophylline A as a Growth-Retarding Agent against the Herbivorous Insect <i>Spodoptera littoralis</i>:  Structure−Activity Relationships
  作者：Gerhard Bringmann、Jörg Holenz、Birgit Wiesen、Bambang W. Nugroho、Peter Proksch

  DOI：10.1021/np960707s

  日期：1997.4.1

  Dioncophylline A (1) represents a novel insecticidal agent, as documented by its enhanced growth-retarding effect on larvae of the polyphagous pest insect Spodoptera littoralis. Within the scope of the work described here, the potential of this as yet most active naphthylisoquinoline alkaloid was further elucidated by the preparation and testing of selected analogues. Investigation of a broad series of structurally modified dioncophylline A analogues (2-20) revealed the free amine function to be essential for the growth inhibitory effect, whereas a modification of the OH function partially led to a distinct increase of activity. In particular, the 8-O-alkyl (especially 8-O-benzylated) derivatives (14 and 15 as well as 16-19) displayed pronounced effects. In the case of 8-O-(p-bromobenzyl)dioncophylline A (16), the activity of the natural parent compound dioncophylline A (1) (EC50 = 277 mu g/g fresh wt of diet; concentration that inhibits larval growth by 50%) was even improved by a factor of >15 (EC50 = 15.6 mu g/g fresh wt).
• BRINGMANN, GERHARD;RUBENACKER, MARTIN;VOGT, PETER;BUSSE, HOLGER;AKE, ASSI+, PHYTOCHEMISTRY, 30,(1991) N, C. 1691-1696
  作者：BRINGMANN, GERHARD、RUBENACKER, MARTIN、VOGT, PETER、BUSSE, HOLGER、AKE, ASSI+

  DOI：——

  日期：——