3-acetyl-4-cyano-7-diethylaminocoumarin | 106695-74-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-acetyl-4-cyano-7-diethylaminocoumarin
• 英文别名: 3-Acetyl-7-(diethylamino)-2-oxochromene-4-carbonitrile
• CAS: 106695-74-3
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: KSRBRVUTCWORHX-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C(Solv: ethanol (64-17-5); chloroform (67-66-3))
• 沸点：
  490.4±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(二乙氨基)水杨醛 在 吗啉 、 碘 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 生成 3-acetyl-4-cyano-7-diethylaminocoumarin
  参考文献：
  名称：

  Synthesis and anti-angiogenesis activity of coumarin derivatives

  摘要：

  A series of 7-diethylaminocoumarin compounds were synthesized and the cytotoxicities were tested against human umbilical vein endothelial cell (HUVEC) and some cancer cells. We found that the introduction of cyano groups at the 4-position will promote the bioactivity. In particular, compounds 9 and 10 strongly inhibited the proliferation of various cancer cell lines, and 12 and 15 showed a high selectivity for HUVEC. Therefore, these coumarin molecules can be utilized as lead compounds to develop potential nontoxic angiogenesis inhibitors and small molecular ligands to target HUVEC. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.007

文献信息

• Chemoselective Fluorgenic Molecular Linkers and Methods for Their Preparation and Use
  申请人：Wang Qian

  公开号：US20070224695A1

  公开（公告）日：2007-09-27

  The present invention describes a bioconjugation strategy and compounds that are useful therein in which a fluorescent signal is produced when two molecular or supramolecular entities are linked by chemoselective combination of one linker having an azido or halide substituent group with another linker having a cyano or an alkyne substituent group. A kit is also provided.

  本发明描述了一种生物共轭策略和在其中有用的化合物，当两个分子或超分子实体通过一个含有偶氮基或卤素取代基的连接剂与另一个含有氰基或炔基取代基的连接剂进行化学选择性组合时，会产生荧光信号。同时还提供了一种试剂盒。
• Chandrasekhar, Anjana; Padmanabhan, S.; Seshadri, S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 137 - 140
  作者：Chandrasekhar, Anjana、Padmanabhan, S.、Seshadri, S.

  DOI：——

  日期：——
• CHANDRASEKHAR A.; PADMANABHAN S.; SESHADRI S., INDIAN J. CHEM., 25,(1986) N 2, 137-140
  作者：CHANDRASEKHAR A.、 PADMANABHAN S.、 SESHADRI S.

  DOI：——

  日期：——
• US7745229B2
  申请人：——

  公开号：US7745229B2

  公开（公告）日：2010-06-29
• Synthesis and anti-angiogenesis activity of coumarin derivatives
  作者：Seokjoon Lee、Krishnamoorthy Sivakumar、Woon-Seob Shin、Fang Xie、Qian Wang

  DOI：10.1016/j.bmcl.2006.06.007

  日期：2006.9

  A series of 7-diethylaminocoumarin compounds were synthesized and the cytotoxicities were tested against human umbilical vein endothelial cell (HUVEC) and some cancer cells. We found that the introduction of cyano groups at the 4-position will promote the bioactivity. In particular, compounds 9 and 10 strongly inhibited the proliferation of various cancer cell lines, and 12 and 15 showed a high selectivity for HUVEC. Therefore, these coumarin molecules can be utilized as lead compounds to develop potential nontoxic angiogenesis inhibitors and small molecular ligands to target HUVEC. (c) 2006 Elsevier Ltd. All rights reserved.