10-(4-hydroxy-3-methoxyphenyl)-2-methyl-6,7,9,10-tetrahydro-1H-furo[3,4-b]pyrrolo[2,3-f]quinolin-9-one | 1380422-93-4

• 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: 10-(4-hydroxy-3-methoxyphenyl)-2-methyl-6,7,9,10-tetrahydro-1H-furo[3,4-b]pyrrolo[2,3-f]quinolin-9-one
• 英文别名: 10-(3-hydroxy-4-methoxyphenyl)-2-methyl-6,7,9,10-tetrahydro-1H-furo[3,4-b]pyrrolo[2,3-f]quinolin-9-one；16-(3-Hydroxy-4-methoxyphenyl)-4-methyl-13-oxa-3,10-diazatetracyclo[7.7.0.02,6.011,15]hexadeca-1(9),2(6),4,7,11(15)-pentaen-14-one
• CAS: 1380422-93-4
• 化学式: C₂₁H₁₈N₂O₄
• 分子量: 362.385
• InChiKey: PGWCNAGWNDBVOL-UHFFFAOYSA-N

物化性质

• 沸点：
  643.4±55.0 °C(predicted)
• 密度：
  1.47±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-羟乙酰乙酸内酯 、 5-氨基-2-甲基吲哚 、 香草醛 以 乙醇 为溶剂， 反应 1.0h， 以85%的产率得到10-(4-hydroxy-3-methoxyphenyl)-2-methyl-6,7,9,10-tetrahydro-1H-furo[3,4-b]pyrrolo[2,3-f]quinolin-9-one
  参考文献：
  名称：

  Synthesis, cytotoxic activity and docking studies of new 4-aza-podophyllotoxin derivatives

  摘要：

  The synthesized nine aza-podophyllotoxin derivatives (8a-f, 10, 12 and 14) have been evaluated for their cytotoxicity in a panel of tumor cancer cell lines (Zr-75-1, MCF7, KB, Gurav, DWD, Colo-205, A-549 and Hop62). Among them, 8a and 8b compounds show stronger growth inhibition activity than the standard drug etoposide. Further, molecular docking simulations were carried out against human topoisomerase II, a putative target for these classes of molecules.

  DOI：

  10.1007/s00044-015-1375-z

文献信息

• [EN] 4-AZA-2, 3-DIDEHYDROPODOPHYLLOTOXIN COMPOUNDS AND PROCESS FOR THE PREPARATION THEREOF<br/>[FR] COMPOSÉS DE 4-AZA-2, 3-DIDÉSHYDROPODOPHYLLOTOXINE ET PROCÉDÉS DE PRÉPARATION DE CEUX-CI
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2012076942A1

  公开（公告）日：2012-06-14

  The present invention provides 4-Aza-2,3-didehydropodophyllotoxin compound of general formula A (4a- 4z and 4aa-4ae) as useful potential antitumour agents against human cancer cell lines. The present invention further provides a process for the synthesis of 4-Aza-2,3-didehydropodophyllotoxin compounds (4a-4z and 4aa-4ae).

  本发明提供了通式A（4a-4z和4aa-4ae）的4-Aza-2,3-didehydropodophyllotoxin化合物，作为潜在的抗人类癌细胞系药物。本发明还提供了一种合成4-Aza-2,3-didehydropodophyllotoxin化合物（4a-4z和4aa-4ae）的方法。
• 4-AZA-2, 3-DIDEHYDROPODOPHYLLOTOXIN COMPOUNDS AND PROCESS FOR THE PREPARATION THEREOF
  申请人：Ahmed Kamal

  公开号：US20130245048A1

  公开（公告）日：2013-09-19

  The present invention provides 4-Aza-2,3-didehydropodophyllotoxin compound of general formula A (4a-4z and 4aa-4ae) as useful potential antitumour agents against human cancer cell lines. The present invention further provides a process for the synthesis of 4-Aza-2,3-didehydropodophyllotoxin compounds (4a-4z and 4aa-4ae).
• US8927560B2
  申请人：——

  公开号：US8927560B2

  公开（公告）日：2015-01-06
• Synthesis, cytotoxic activity and docking studies of new 4-aza-podophyllotoxin derivatives
  作者：Islavathu Hatti、Reddymasu Sreenivasulu、Surender Singh Jadav、Venkatesan Jayaprakash、C. Ganesh Kumar、Rudraraju Ramesh Raju

  DOI：10.1007/s00044-015-1375-z

  日期：2015.8

  The synthesized nine aza-podophyllotoxin derivatives (8a-f, 10, 12 and 14) have been evaluated for their cytotoxicity in a panel of tumor cancer cell lines (Zr-75-1, MCF7, KB, Gurav, DWD, Colo-205, A-549 and Hop62). Among them, 8a and 8b compounds show stronger growth inhibition activity than the standard drug etoposide. Further, molecular docking simulations were carried out against human topoisomerase II, a putative target for these classes of molecules.