2-amino-4-(2-chloro-6-fluorophenyl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile | 728884-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-amino-4-(2-chloro-6-fluorophenyl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile
• 英文别名: 2-amino-4-(2-chloro-6-fluorophenyl)-5,10-dioxo-4H-benzo[g]chromene-3-carbonitrile
• CAS: 728884-07-9
• 化学式: C₂₀H₁₀ClFN₂O₃
• 分子量: 380.762
• InChiKey: WXAIZBRADVGZNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氯-6-氟-苯甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 2-amino-4-(2-chloro-6-fluorophenyl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile
  参考文献：
  名称：

  Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-Pyrano-[2,3-b]naphthoquinones with anticancer activity

  摘要：

  4H-Pyrano-[2,3-b]naphthoquinone is a structural motif commonly found in natural products manifesting anticancer activities. As part of a program aimed at structural simplification of bioactive natural products utilizing multicomponent synthetic processes, we developed a compound library based on this heterocyclic scaffold. We found that several library members displayed low micromolar antiproliferative activity and induced apoptosis in human cancer cells. Selected compounds showed promising activity against cancer cell lines resistant to proapoptotic stimuli, demonstrating their potential in treating cancers with dismal prognoses. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.073

文献信息

• Facile one-pot green synthesis of 2-amino-4<i>H</i>-benzo[<i>g</i>]chromenes in aqueous ethanol under ultrasound irradiation
  作者：Shabalala Nhlanhla Gracious、Nagaraju Kerru、Suresh Maddila、Werner E. van Zyl、Sreekantha B. Jonnalagadda

  DOI：10.1080/00397911.2020.1761393

  日期：2020.7.2

  Abstract We report an efficient green one-pot approach for the synthesis of eighteen novel dihydro-4H-benzo[g]chromene derivatives under ultrasound irradiation conditions. The three-component condensation reaction proceeded through Knoevenagel-Michael reaction of chosen active methylene compounds and 2-hydroxynaphthalene-1,4-dione with different substituted aldehydes in the presence of ammonium acetate

  摘要 我们报告了一种在超声辐照条件下合成十八种新型二氢-4H-苯并[g]色烯衍生物的高效绿色一锅法。三组分缩合反应通过选定的活性亚甲基化合物和2-羟基萘-1,4-二酮与不同取代醛的Knoevenagel-Michael反应在醋酸铵的存在下在水和乙醇混合物中在室温下进行，收率高在 5-15 分钟的快速反应时间内生成产品 (91-98%)。该程序提供了 95% 的原子经济和 100% 的碳效率以及其他环保效益。图形概要
• Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-Pyrano-[2,3-b]naphthoquinones with anticancer activity
  作者：Igor V. Magedov、Artem S. Kireev、Aaron R. Jenkins、Nikolai M. Evdokimov、Dustin T. Lima、Paul Tongwa、Jeff Altig、Wim F. A. Steelant、Severine Van slambrouck、Mikhail Yu. Antipin、Alexander Kornienko

  DOI：10.1016/j.bmcl.2012.06.073

  日期：2012.8

  4H-Pyrano-[2,3-b]naphthoquinone is a structural motif commonly found in natural products manifesting anticancer activities. As part of a program aimed at structural simplification of bioactive natural products utilizing multicomponent synthetic processes, we developed a compound library based on this heterocyclic scaffold. We found that several library members displayed low micromolar antiproliferative activity and induced apoptosis in human cancer cells. Selected compounds showed promising activity against cancer cell lines resistant to proapoptotic stimuli, demonstrating their potential in treating cancers with dismal prognoses. (c) 2012 Elsevier Ltd. All rights reserved.