9-(4-hydroxy-3-methoxyphenyl)-5,6,7-trimethoxy-1,3,4,9-tetrahydrofuro[3,4-b]quinolin-1-one | 1305285-54-4

• 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: 9-(4-hydroxy-3-methoxyphenyl)-5,6,7-trimethoxy-1,3,4,9-tetrahydrofuro[3,4-b]quinolin-1-one
• 英文别名: 9-(4-hydroxy-3-methoxyphenyl)-5,6,7-trimethoxy-4,9-dihydro-3H-furo[3,4-b]quinolin-1-one
• CAS: 1305285-54-4
• 化学式: C₂₁H₂₁NO₇
• 分子量: 399.4
• InChiKey: DPAGJRPMLSWORM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-羟乙酰乙酸内酯 、 2,3,4-三甲氧基苯胺 、 香草醛 以 乙醇 为溶剂， 反应 1.0h， 以85%的产率得到9-(4-hydroxy-3-methoxyphenyl)-5,6,7-trimethoxy-1,3,4,9-tetrahydrofuro[3,4-b]quinolin-1-one
  参考文献：
  名称：

  Synthesis of a new 4-aza-2,3-didehydropodophyllotoxin analogues as potent cytotoxic and antimitotic agents

  摘要：

  A series of novel conjugates of 4-aza-2,3-didehydropodophyllotoxins (11a-w) were synthesized by a straightforward one-step multicomponent synthesis that demonstrated cytotoxicity against five human cancer cell lines (breast, oral, colon, lung and ovarian). All the twenty three compounds (11a-w) have been examined for the inhibition of tubulin polymerization. Among these compounds, 11a, 11k and 11p exhibited inhibition of polymerization tubulin comparable to podophyllotoxin apart from disruption of microtubule organization within the cells. Flow cytometric analysis showed that these compounds (11a, 11k and 11p) arrested the cell cycle in the G2/M phase of cell cycle leading to caspase-3 dependent apoptotic cell death. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.020

文献信息

• 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 of a new 4-aza-2,3-didehydropodophyllotoxin analogues as potent cytotoxic and antimitotic agents
  作者：Ahmed Kamal、Paidakula Suresh、Adla Mallareddy、Banala Ashwini Kumar、Papagari Venkat Reddy、Paidakula Raju、Jaki R. Tamboli、Thokhir B. Shaik、Nishant Jain、Shasi V. Kalivendi

  DOI：10.1016/j.bmc.2011.02.020

  日期：2011.4

  A series of novel conjugates of 4-aza-2,3-didehydropodophyllotoxins (11a-w) were synthesized by a straightforward one-step multicomponent synthesis that demonstrated cytotoxicity against five human cancer cell lines (breast, oral, colon, lung and ovarian). All the twenty three compounds (11a-w) have been examined for the inhibition of tubulin polymerization. Among these compounds, 11a, 11k and 11p exhibited inhibition of polymerization tubulin comparable to podophyllotoxin apart from disruption of microtubule organization within the cells. Flow cytometric analysis showed that these compounds (11a, 11k and 11p) arrested the cell cycle in the G2/M phase of cell cycle leading to caspase-3 dependent apoptotic cell death. (C) 2011 Elsevier Ltd. All rights reserved.