2-amino-7-hydroxy-4-(2,3,4-trimethoxyphenyl)-4H-chromene-3-carbonitrile | 1427071-55-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 2-amino-7-hydroxy-4-(2,3,4-trimethoxyphenyl)-4H-chromene-3-carbonitrile
• CAS: 1427071-55-3
• 化学式: C₁₉H₁₈N₂O₅
• 分子量: 354.362
• InChiKey: XWVURMSTWFAOJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  丙二腈 、 间苯二酚 、 2,3,4-三甲氧基苯甲醛 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 生成 2-amino-7-hydroxy-4-(2,3,4-trimethoxyphenyl)-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Comparative in vivo evaluation of polyalkoxy substituted 4H-chromenes and oxa-podophyllotoxins as microtubule destabilizing agents in the phenotypic sea urchin embryo assay

  摘要：

  A series of polyalkoxy substituted 7-hydroxy- and 7-methoxy-4-aryl-4H-chromenes were evaluated using the sea urchin embryo model to yield several compounds exhibiting potent antimitotic microtubule destabilizing activity. Data obtained by the assay were further confirmed in the NCI60 human cancer cell screen. The replacement of methylenedioxy ring A and lactone ring D in podophyllotoxin analogues by 7-methoxy, 2-NH2, and 3-CN groups in 4-aryl-4H-chromenes resulted in potent antimitotic microtubule destabilizing agents. Feasible synthesis and high yields render 7-methoxy-4H-chromenes to be a promising series for further anticancer drug development.

  DOI：

  10.1016/j.bmcl.2014.06.043

文献信息

• New ruthenium(<scp>ii</scp>) catalysts enable the synthesis of 2-amino-4<i>H</i>-chromenes using primary alcohols <i>via</i> acceptorless dehydrogenative coupling
  作者：Veerappan Tamilthendral、Rengan Ramesh、Jan Grzegorz Malecki

  DOI：10.1039/d2nj03268f

  日期：——

  acceptorless dehydrogenative coupling of substituted benzyl alcohols, resorcinol, and malononitrile. The present catalytic protocol furnishes a variety of 2-amino-4H-chromenes in high yields of up to 95% from a wide range of readily available primary alcohols without the use of any oxidant/additives utilizing low catalyst loading. A plausible mechanism for the catalytic synthesis of 2-amino-4H-chromene compounds

  通过包含 N-O 螯合咔唑基腙配体的对伞花烃 Ru( II ) 有机金属络合物催化的一锅多组分反应，合成了一系列具有不同取代基功能的具有生物学意义的 2-氨基-4 H-色烯。使用各种光谱（FT-IR、UV-vis、NMR 和 HR-MS）和分析方法合成和表征了一组对伞花烃 Ru( II ) 配合物。借助单晶 X 射线衍射研究证实了其中一种配合物的分子结构。2-氨基-4 H-色烯衍生物已在温和条件下通过钌( II) 催化剂介导的取代苯甲醇、间苯二酚和丙二腈的无受体脱氢偶联。本催化协议提供了各种 2-氨基-4 H-色烯，从各种容易获得的伯醇中以高达 95% 的高产率提供，而无需使用任何利用低催化剂负载的氧化剂/添加剂。通过醛和亚苄基丙二腈中间体的形成以及水和氢作为副产物的排放，已经描述了催化合成 2-氨基-4 H-色烯化合物的合理机制。有趣的是，从合成的 2-氨基-4 H-色烯中成功构建了具有良好收率的药用重要的他克林类似物。
• Comparative in vivo evaluation of polyalkoxy substituted 4H-chromenes and oxa-podophyllotoxins as microtubule destabilizing agents in the phenotypic sea urchin embryo assay
  作者：Marina N. Semenova、Dmitry V. Tsyganov、Oleg R. Malyshev、Oleg V. Ershov、Ivan N. Bardasov、Roman V. Semenov、Alex S. Kiselyov、Victor V. Semenov

  DOI：10.1016/j.bmcl.2014.06.043

  日期：2014.8

  A series of polyalkoxy substituted 7-hydroxy- and 7-methoxy-4-aryl-4H-chromenes were evaluated using the sea urchin embryo model to yield several compounds exhibiting potent antimitotic microtubule destabilizing activity. Data obtained by the assay were further confirmed in the NCI60 human cancer cell screen. The replacement of methylenedioxy ring A and lactone ring D in podophyllotoxin analogues by 7-methoxy, 2-NH2, and 3-CN groups in 4-aryl-4H-chromenes resulted in potent antimitotic microtubule destabilizing agents. Feasible synthesis and high yields render 7-methoxy-4H-chromenes to be a promising series for further anticancer drug development.