4,5,3',4'-tetramethoxy-2-vinyl-stilbene | 94757-36-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4,5,3',4'-tetramethoxy-2-vinyl-stilbene
• 英文别名: 4,5,3',4'-Tetramethoxy-2-vinyl-stilben；Laudanosen
• CAS: 94757-36-5
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: AILUBGXVNJUJEG-UHFFFAOYSA-N

物化性质

• 沸点：
  491.2±45.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,5,3',4'-tetramethoxy-2-vinyl-stilbene 在 硝酸 、 溶剂黄146 作用下， 生成 (+/-)-1-(4,5-dimethoxy-2-nitro-benzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline
  参考文献：
  名称：

  Effects of L-dopa treatment on methylation in mouse brain: Implications for the side effects of L-dopa

  摘要：

  The effects of L-dopa on methylation process in the mouse brain were investigated. The study is based on recent findings that methylation may play an important role in Parkinson's disease (PD) and in the actions of L-dopa. The methyl donor, S-adenosylmethionine (SAM) and a product of SAM, methyl beta-carboline, were shown to cause PD-like symptoms, when injected into the brain of animals. Furthermore, large amounts of 3-O-methyl dopa, the methyl product of L-dopa, are produced in PD patients receiving L-dopa treatment, and L-dopa induces methionine adenosyl transferase, the enzyme that produces SAM. The results show that, at 0.5 hr, L-dopa (100 mg/kg) decreased the methyl donor, S-adenosylmethionine (SAM) by 36%, increased its metabolite S-adenosylhomocysteine (SAH) by 89% and increased methylation (SAH/SAM) by about 200%. All parameters returned to control values within 4 hr. But 2, 3 and 4 consecutive injections of L-dopa, given at 45 min intervals, depleted SAM by 60, 64 and 76% and increased SAM/SAH to 818, 896, and 1524%. L-dopa (50, 100 and 200 mg/kg) dose-dependently depleted SAM from 24.9 +/- 1.7 nmol/g to 13.0 +/- 0.8, 14.7 +/- 0.8 and 7.7 +/- 0.7 nmol/g, and increased SAH from 1.88 +/- 0.14 to 3.43 +/- 0.26, 4.22 +/- 0.32 and 6.21 +/- 0.40 nmol/g. Brain L-dopa was increased to 326, 335 and 779%, dopamine to 138, 116 and 217% and SAH/SAM to 354, 392 and 1101%. The data show that L-dopa depletes SAM, and increases methylation 4-5 times more than dopamine, therefore, methylation may play a role in the actions of L-dopa. This and other studies suggest that the high level of utilization of methyl group by L-dopa leads to the induction of enzymes to replenish SAM and to increase the methylation of L-dopa as well as DA. These changes may be involved in the side effects of L-dopa.

  DOI：

  10.1016/s0024-3205(00)00557-9
• 作为产物：
  描述：

  Laudanosin-methin-methohydroxyd 在 氢氧化钾 作用下， 生成 4,5,3',4'-tetramethoxy-2-vinyl-stilbene
  参考文献：
  名称：

  459.生物碱的苄基异喹啉和邻苯二甲酰异喹啉系列中的氧化胺热解和霍夫曼降解

  摘要：

  DOI：

  10.1039/jr9630002491

文献信息

• Die Konfiguration des natürlichen (+)-Laudanosins sowie verwandter Tetrahydro-isochinolin-, Aporphin- und Tetrahydro-berberin-Alkaloide
  作者：H. Corrodi、E. Hardegger

  DOI：10.1002/hlca.19560390333

  日期：——

  wurde in die optischen Antipoden gespalten. Die reduktive Methylierung des (−)-N-Nor-laudanosins gab rlatiirliches (+)-Laudanosin, wahrend der Abbau mit Ozon und Perameisensaure zu einem L-Asparaginssure-Derivat fuhrte. Damit ist die fruher nur auf Grund der Clough'schen Regel abgeleitete Konfiguration des natürlichen (+)-Laudanosins streng bewiesen. Aus unserer Beweisführung ergibt sich auch die Konfiguration

  罂粟中的1N-Norlaudanosin（Tetrahydro-papaverin）炸药包装在Optischen Antipoden gespalten中。还原甲基（-）-N-Nor-laudanosins gab rlatiirliches（+）-Laudanosin，作者是Abzon mit Ozon和Perameisensaure zu Einem L-Asparaginssure-Derivat fuhrte。国防军在纳尔·克劳德·克劳夫氏父子的统治下继续前进，纳特里琴（+）-劳丹诺辛菌强化了他的力量。不可抗药性的发生是由于本位制人安扎尔·威特尔（Alzaloide der Tetrahydro-isochinolin-），der Aporphin和der Tetrahydro-berberin-Reihe所致。
• Spaeth; Epstein, Chemische Berichte, 1928, vol. 61, p. 340
  作者：Spaeth、Epstein

  DOI：——

  日期：——
• Gadamer; Knoch, Archiv der Pharmazie, 1921, vol. 259, p. 149
  作者：Gadamer、Knoch

  DOI：——

  日期：——
• Schoepf; Thierfelder, Justus Liebigs Annalen der Chemie, 1932, vol. 497, p. 22,33
  作者：Schoepf、Thierfelder

  DOI：——

  日期：——
• 103. Preliminary synthetic experiments in the morphine group. Part IV. A dehydro-derivative of laudanosoline hydrochloride and its constitution
  作者：Robert Robinson、Shigehiko Sugasawa

  DOI：10.1039/jr9320000789

  日期：——