5,6-dihydro-8-hydroxy-9-methoxy-N-methyl-2,3-methylenedioxybenzo[c]phenanthridine | 115522-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5,6-dihydro-8-hydroxy-9-methoxy-N-methyl-2,3-methylenedioxybenzo[c]phenanthridine
• 英文别名: dihydroterihanine；3-methoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridin-2-ol
• CAS: 115522-75-3
• 化学式: C₂₀H₁₇NO₄
• 分子量: 335.359
• InChiKey: YDBJVOYZKCNQOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  588.3±50.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-dihydro-8-hydroxy-9-methoxy-N-methyl-2,3-methylenedioxybenzo[c]phenanthridine 在 Jones reagent 、 盐酸 作用下， 以 丙酮 、 水 为溶剂， 反应 0.5h， 以32%的产率得到terihanine chloride
  参考文献：
  名称：

  Total Synthesis of the Benzo[c]phenanthridine Alkaloids, Terihanine and Isoterihanine, and Their Antitumor Activity

  摘要：

  A new total synthesis of terihanine (2a) and isoterihanine (2b) was established by our new bond formation between the C4b and N5 positions of the benzo[c]phenanthridine ring based on a microwave-assisted thermal electrocyclic reaction of 2-cycloalkenylbenzaldoxime as an aza 6 pi-electron system. In addition, the antitumor activity of these synthesized compounds, including nitidine and nornitidine was evaluated in HCT-116 cells.

  DOI：

  10.3987/com-13-s(s)16
• 作为产物：
  描述：

  2-溴-5-羟基-4-甲氧基苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 硫酸 、 palladium 10% on activated carbon 、 sodium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 邻二氯苯 、 乙腈 为溶剂， 反应 78.0h， 生成 5,6-dihydro-8-hydroxy-9-methoxy-N-methyl-2,3-methylenedioxybenzo[c]phenanthridine
  参考文献：
  名称：

  Total Synthesis of the Benzo[c]phenanthridine Alkaloids, Terihanine and Isoterihanine, and Their Antitumor Activity

  摘要：

  A new total synthesis of terihanine (2a) and isoterihanine (2b) was established by our new bond formation between the C4b and N5 positions of the benzo[c]phenanthridine ring based on a microwave-assisted thermal electrocyclic reaction of 2-cycloalkenylbenzaldoxime as an aza 6 pi-electron system. In addition, the antitumor activity of these synthesized compounds, including nitidine and nornitidine was evaluated in HCT-116 cells.

  DOI：

  10.3987/com-13-s(s)16

文献信息

• Studies on the chemical constituents of rutaceous plants. LXIV. Structural establishment of oxyterihanine, a phenolic benzo[c]phenanthridone alkaloid. Syntheses of phenolic benzo[c]phenanthridine alkaloids, terihanine and isoterihanine, and related compounds.
  作者：HISASHI ISHII、IH-SHENG CHEN、SATOSHI UEKI、MISAKO AKAIKE、TSUTOMU ISHIKAWA

  DOI：10.1248/cpb.35.2717

  日期：——

  The structure of oxyterihanine (2c), a new phenolic benzo [c] phenanthridone alkaloid which was isolated from Formosan Xanthoxylum nitidum (ROXB.) D. C. (Fagara nitida ROXB.), was established as 8-hydroxy-9-methoxy-5-methyl-2, 3-methylenedioxybenzo [c] phenanthridin-6 (5H) one by direct comparison with a synthetic specimen, which was derived from 2- (4-isopropoxy-3-methoxyphenyl) -6, 7-methylenedioxy-3, 4-dihydronaphthalen-1 (2H) -one (8a) through the synthetic sequence shown in Charts 3 and 4. 9-Hydroxy-8-methoxy-5-methyl-2, 3-methylenedioxybenzo [c] phenanthridin-6 (5H) -one [oxyisoterihanine (2d)] and two phenolic quaternary benzo [c] phenanthridine alkaloids, terihanine (1c) and isoterihanine (1d), were also synthesized.

  oxyterihanine (2c) 是从台湾两面针 (Fagara nitida ROXB.) 中分离出来的一种新型酚类苯并[c]菲啶酮生物碱，其结构被确定为 8-羟基-9-甲氧基-5-甲基-2, 3-亚甲基二氧基苯并[c]菲啶-6 (5H) 1，通过与合成样品直接比较，合成样品衍生自 2- (4-异丙氧基-3-甲氧基苯基) -6, 7-亚甲基二氧基-3, 4-二氢萘-1 (2H) -酮 (8a) 通过图 3 和图 4 所示的合成顺序进行。 9-羟基-8-甲氧基-5-甲基-2, 3-亚甲基二氧基苯并[c] 菲啶-6 (5H) -酮还合成了[oxyisoterihanine (2d)]和两种酚季苯并[c]菲啶生物碱terihanine (1c) 和isoterihanine (1d)。
• ISHII, HISASHI;CHEN, IH-SHENG;UEKI, SATOSHI;AKAIKE, MISAKO;ISHIKAWA, TSUT+, CHEM. AND PHARM. BULL., 35,(1987) N 7, 2717-2725
  作者：ISHII, HISASHI、CHEN, IH-SHENG、UEKI, SATOSHI、AKAIKE, MISAKO、ISHIKAWA, TSUT+

  DOI：——

  日期：——