9-(2,5-dimethoxy-3,4-methyledioxyphenyl)-7-methoxy-3,9-dihydro-1H-furo[3,4-b]chromen-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-(2,5-dimethoxy-3,4-methyledioxyphenyl)-7-methoxy-3,9-dihydro-1H-furo[3,4-b]chromen-1-one
• 英文别名: 9-(4,7-Dimethoxy-1,3-benzodioxol-5-yl)-6-methoxy-3,9-dihydrofuro[3,4-b]chromen-1-one
• 化学式: C₂₁H₁₈O₈
• 分子量: 398.369
• InChiKey: RBOAKPUWPBGXKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  洋芹脑 在 吡啶 、 四丁基溴化铵 、 臭氧 、 溶剂黄146 、 potassium hydroxide 作用下， 以 甲醇 、 氯仿 、 水 、 甲苯 为溶剂， 反应 1.17h， 生成 9-(2,5-dimethoxy-3,4-methyledioxyphenyl)-7-methoxy-3,9-dihydro-1H-furo[3,4-b]chromen-1-one
  参考文献：
  名称：

  Synthesis and comparative evaluation of 4-oxa- and 4-aza-podophyllotoxins as antiproliferative microtubule destabilizing agents

  摘要：

  A series of novel 4-oxa-podophyllotoxin derivatives 7 featuring the intact lactone ring D and various substituents in rings B and E has been synthesized and evaluated in a phenotypic sea urchin embryo assay along with the representative 4-aza-analogs 5 for their antimitotic and microtubule destabilizing activity. The most active compounds exhibited myristicin-derived or a 3',5'-dimethoxy substitution pattern in the ring E and a 6-methoxy moiety replacing the methylenedioxy ring A. Compounds 5xb, 5xe, 5yb, 7xa, 7xb, and 7xc showed potent antiproliferative effects in the NCI60 cytotoxicity screen. Notably, growth of the multi-drug resistant NCI/ADR-RES cells was more affected by these agents than the parent OVCAR-8 cell line. Although generally 4-oxa-podophyllotoxins were less potent than the respective 4-aza-derivatives in these assays, stability of the former series towards oxidation may prove to be of interest for the development of anticancer agents with in vivo activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.128

文献信息

• Synthesis and comparative evaluation of 4-oxa- and 4-aza-podophyllotoxins as antiproliferative microtubule destabilizing agents
  作者：Natalia B. Chernysheva、Dmitry V. Tsyganov、Alex A. Philchenkov、Michael P. Zavelevich、Alex S. Kiselyov、Roman V. Semenov、Marina N. Semenova、Victor V. Semenov

  DOI：10.1016/j.bmcl.2012.01.128

  日期：2012.4

  A series of novel 4-oxa-podophyllotoxin derivatives 7 featuring the intact lactone ring D and various substituents in rings B and E has been synthesized and evaluated in a phenotypic sea urchin embryo assay along with the representative 4-aza-analogs 5 for their antimitotic and microtubule destabilizing activity. The most active compounds exhibited myristicin-derived or a 3',5'-dimethoxy substitution pattern in the ring E and a 6-methoxy moiety replacing the methylenedioxy ring A. Compounds 5xb, 5xe, 5yb, 7xa, 7xb, and 7xc showed potent antiproliferative effects in the NCI60 cytotoxicity screen. Notably, growth of the multi-drug resistant NCI/ADR-RES cells was more affected by these agents than the parent OVCAR-8 cell line. Although generally 4-oxa-podophyllotoxins were less potent than the respective 4-aza-derivatives in these assays, stability of the former series towards oxidation may prove to be of interest for the development of anticancer agents with in vivo activity. (C) 2012 Elsevier Ltd. All rights reserved.