3-(4-chlorophenyl)-4-(3-hydroxy-4-methoxyphenyl)-4,5,7,8-tetrahydrofuro[3',4':5,6]pyrido[3,2-d]isoxazol-5-one | 1305285-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(4-chlorophenyl)-4-(3-hydroxy-4-methoxyphenyl)-4,5,7,8-tetrahydrofuro[3',4':5,6]pyrido[3,2-d]isoxazol-5-one
• 英文别名: 6-(4-Chlorophenyl)-8-(3-hydroxy-4-methoxyphenyl)-4,11-dioxa-2,5-diazatricyclo[7.3.0.03,7]dodeca-1(9),3(7),5-trien-10-one；6-(4-chlorophenyl)-8-(3-hydroxy-4-methoxyphenyl)-4,11-dioxa-2,5-diazatricyclo[7.3.0.03,7]dodeca-1(9),3(7),5-trien-10-one
• CAS: 1305285-53-3
• 化学式: C₂₁H₁₅ClN₂O₅
• 分子量: 410.813
• InChiKey: AQCKEGOIHCCDSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  93.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  异香兰素 、 4-羟乙酰乙酸内酯 、 5-氨基-3-(4-氯苯基)异噁唑 以 乙醇 为溶剂， 反应 1.0h， 以85%的产率得到3-(4-chlorophenyl)-4-(3-hydroxy-4-methoxyphenyl)-4,5,7,8-tetrahydrofuro[3',4':5,6]pyrido[3,2-d]isoxazol-5-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

• [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：Council of Scientific & Industrial Research

  公开号：EP2649078B1

  公开（公告）日：2016-07-27
• 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.