9-(3,4,5-Trimethoxy-phenyl)-6,7-dihydro-1,3-dioxa-5-aza-dicyclopenta[b,g]naphthalen-8-one | 200053-32-3

• 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: 9-(3,4,5-Trimethoxy-phenyl)-6,7-dihydro-1,3-dioxa-5-aza-dicyclopenta[b,g]naphthalen-8-one
• 英文别名: 8-(3,4,5-Trimethoxyphenyl)-12,14-dioxa-2-azatetracyclo[7.7.0.03,7.011,15]hexadeca-1(16),2,7,9,11(15)-pentaen-6-one
• CAS: 200053-32-3
• 化学式: C₂₂H₁₉NO₆
• 分子量: 393.396
• InChiKey: OSMNKYVBDSQMIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  76.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-(3,4,5-Trimethoxy-phenyl)-6,7-dihydro-1,3-dioxa-5-aza-dicyclopenta[b,g]naphthalen-8-one 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以52%的产率得到(+/-)-6,7-methylenedioxy-9-(3,4,5-trimethoxyphenyl)-2,3,4,9-tetrahydrocyclopenta[b]quinolin-1-one
  参考文献：
  名称：

  4-Aza-2,3-dehydro-4-deoxypodophyllotoxins: simple aza-podophyllotoxin analogues possessing potent cytotoxicity

  摘要：

  4-Aza-2,3-dehydro-4-deoxypodophyllotoxin analogues 3a-n were synthesized through quinolines 2a-n. Comparison of their cytotoxicity against P-388 leukemia cells revealed that the steric effects of the ring B substituents on the activity are greater than the electronic effects, while the presence of a methoxy group on the ring E is not essential to exhibit potent cytotoxicity. Analogues 3a and 3b proved to be more than twice as cytotoxic as natural podophyllotoxin (1). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00693-9
• 作为产物：
  描述：

  3,4-亚甲二氧基苯胺 在 四氯苯醌 、 三氟乙酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 9-(3,4,5-Trimethoxy-phenyl)-6,7-dihydro-1,3-dioxa-5-aza-dicyclopenta[b,g]naphthalen-8-one
  参考文献：
  名称：

  轻松合成1-芳基萘木脂素chinensin，justicidin B和Taiwanin C的4-氮杂类似物

  摘要：

  苯胺1a-d与tetronic酸（2）或1,3-环戊二酮（3）反应分别生成苯胺内酯4a-d和苯胺基环戊烯酮5a，然后与苯甲醛缩合生成4-氮杂-1-芳基萘木脂素类似物6 –19。

  DOI：

  10.1016/s0040-4039(97)10204-0

文献信息

• A facile synthesis of the 4-aza-analogs of 1-arylnaphthalene lignans chinensin, justicidin B, and Taiwanin C
  作者：Yukio Hitotsuyanagi、Masatsugu Kobayashi、Masamoto Fukuyo、Koichi Takeya、Hideji Itokawa

  DOI：10.1016/s0040-4039(97)10204-0

  日期：1997.12

  tetronic acid (2) or 1,3-cyclopentanedione (3) produced anilinolactones 4a-d and anilinocyclopentenone 5a, respectively, which were then condensed with benzaldehydes to yield 4-aza-1-arylnaphthalene lignan analogs 6–19.

  苯胺1a-d与tetronic酸（2）或1,3-环戊二酮（3）反应分别生成苯胺内酯4a-d和苯胺基环戊烯酮5a，然后与苯甲醛缩合生成4-氮杂-1-芳基萘木脂素类似物6 –19。
• 4-Aza-2,3-dehydro-4-deoxypodophyllotoxins: simple aza-podophyllotoxin analogues possessing potent cytotoxicity
  作者：Yukio Hitotsuyanagi、Masamoto Fukuyo、Kyoko Tsuda、Masatsugu Kobayashi、Akira Ozeki、Hideji Itokawa、Koichi Takeya

  DOI：10.1016/s0960-894x(99)00693-9

  日期：2000.2

  4-Aza-2,3-dehydro-4-deoxypodophyllotoxin analogues 3a-n were synthesized through quinolines 2a-n. Comparison of their cytotoxicity against P-388 leukemia cells revealed that the steric effects of the ring B substituents on the activity are greater than the electronic effects, while the presence of a methoxy group on the ring E is not essential to exhibit potent cytotoxicity. Analogues 3a and 3b proved to be more than twice as cytotoxic as natural podophyllotoxin (1). (C) 2000 Elsevier Science Ltd. All rights reserved.