2-amino-5,10-dioxo-4-(pyridin-4-yl)-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile | 1019060-38-8

• 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-5,10-dioxo-4-(pyridin-4-yl)-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile
• 英文别名: 2-amino-5,10-dioxo-4-pyridin-4-yl-4H-benzo[g]chromene-3-carbonitrile
• CAS: 1019060-38-8
• 化学式: C₁₉H₁₁N₃O₃
• 分子量: 329.315
• InChiKey: VAVGZYFBRIMTER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 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：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-吡啶甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 2-amino-5,10-dioxo-4-(pyridin-4-yl)-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

• Zn(<scp>L</scp>-proline)₂as a powerful and reusable organometallic catalyst for the very fast synthesis of 2-amino-4<i>H</i>-benzo[<i>g</i>]chromene derivatives under solvent-free conditions
  作者：Behrooz Maleki、Saeed Babaee、Reza Tayebee

  DOI：10.1002/aoc.3306

  日期：2015.6

  An efficient route for the synthesis of 2‐amino‐4H‐benzo[g]chromenes via a three‐component coupling reaction of aldehydes, malononitrile and 2‐hydroxy‐1,4‐naphthaquinone in the presence of Zn( L‐proline)2 is reported. High yields, short reaction times, non‐toxicity and recyclability of the catalyst, and easy work‐up are the main merits of this protocol. Copyright © 2015 John Wiley & Sons, Ltd.

  在锌（L-脯氨酸）存在下，醛，丙二腈和2-羟基-1,4-萘醌的三组分偶联反应合成2-氨基-4 H-苯并[ g ]色烯的有效途径报告2。该方案的主要优点是高收率，较短的反应时间，催化剂的无毒性和可回收性以及易于后处理。版权所有©2015 John Wiley＆Sons，Ltd.
• 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.