4-(7-(diethylamino)-4-methyl-2-oxo-2H-chromen-3-yl)benzaldehyde | 1114962-65-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4-(7-(diethylamino)-4-methyl-2-oxo-2H-chromen-3-yl)benzaldehyde
• 英文别名: 4-[7-(diethylamino)-4-methyl-2-oxo-2H-1-benzopyran-3-yl]benzaldehyde；7-diethylamino-4-methyl-3-(4-formylphenyl)coumarin；4-[7-(Diethylamino)-4-methyl-2-oxochromen-3-yl]benzaldehyde
• CAS: 1114962-65-0
• 化学式: C₂₁H₂₁NO₃
• 分子量: 335.403
• InChiKey: STPNTXDOWKJTIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  542.6±50.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(7-(diethylamino)-4-methyl-2-oxo-2H-chromen-3-yl)benzaldehyde 、 丙酮 在 四氢吡咯 作用下， 以 水 为溶剂， 生成 7-diethylamino-3-[4-(1-hydroxy-3-oxobutyl)phenyl]-4-methylchromen-2-one
  参考文献：
  名称：

  A Fluorogenic Aldehyde Bearing a 1,2,3-Triazole Moiety for Monitoring the Progress of Aldol Reactions

  摘要：

  We have developed a new type of fluorogenic aldehyde bearing a 1,2,3-triazole moiety that is useful for monitoring the progress of aldol reactions through an increase in fluorescence. Whereas 6-methoxy-2-naphthaldehyde was highly fluorescent, the fluorogenic aldehyde, 4-formylbenzene connected to the 6-methoxy-2-naphthyl group through a 1,2,3-triazole moiety, was essentially nonfluorescent in aqueous solutions. We suggest that the 4-formylphenyl group acts as a quencher to suppress the fluorescence of the 6-methoxy-2-naphthyltriazole moiety. The product of the aldol reaction of this aldehyde does not have a quenching moiety and showed more than 800-fold higher fluorescence than the aldehyde. Assay systems using the fluorogenic aldehyde were validated by screening of aldol catalysts, ranking of the activities of the catalysts, and evaluation of reaction conditions.

  DOI：

  10.1021/jo900013w
• 作为产物：
  描述：

  7-二乙氨基-4-甲基香豆素 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 ammonium acetate 、 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 73.0h， 生成 4-(7-(diethylamino)-4-methyl-2-oxo-2H-chromen-3-yl)benzaldehyde
  参考文献：
  名称：

  兴奋性氨基酸转运蛋白亚型1选择性抑制剂基于香豆素的荧光类似物的设计，合成和药理学表征

  摘要：

  兴奋性氨基酸转运蛋白（EAAT）在调节哺乳动物中枢神经系统中谷氨酸的突触浓度中起关键作用。迄今为止，已鉴定出五种不同的亚型，在人类中名为EAAT15（在啮齿动物中分别为GLAST，GLT-1，EAAC1，EAAT4和EAAT5）。最近，我们发表并提出了一种新型的EAAT1（和GLAST）选择性抑制剂的结构-活性关系（SAR）研究，其类似物为UCPH-101（IC 50  = 0.66μM ）和UCPH-102（IC 50  = 0.43μM）是该系列中最有效的抑制剂。在本文中，我们介绍了六种基于香豆素的UCPH-101 / 102荧光素类似物作为EAAT1亚型选择性抑制剂的设计，合成和药理学评估。类似物1114未能抑制EAAT1功能（IC 50值> 300μM），而类似物15和UCPH-102F抑制EAAT1，IC 50值处于中等微摩尔范围（分别为17μM和14μM ）。在生理pH下，类似

  DOI：

  10.1016/j.bmc.2012.09.049

文献信息

• A Fluorogenic Aldehyde Bearing a 1,2,3-Triazole Moiety for Monitoring the Progress of Aldol Reactions
  作者：Hai-Ming Guo、Fujie Tanaka

  DOI：10.1021/jo900013w

  日期：2009.3.20

  We have developed a new type of fluorogenic aldehyde bearing a 1,2,3-triazole moiety that is useful for monitoring the progress of aldol reactions through an increase in fluorescence. Whereas 6-methoxy-2-naphthaldehyde was highly fluorescent, the fluorogenic aldehyde, 4-formylbenzene connected to the 6-methoxy-2-naphthyl group through a 1,2,3-triazole moiety, was essentially nonfluorescent in aqueous solutions. We suggest that the 4-formylphenyl group acts as a quencher to suppress the fluorescence of the 6-methoxy-2-naphthyltriazole moiety. The product of the aldol reaction of this aldehyde does not have a quenching moiety and showed more than 800-fold higher fluorescence than the aldehyde. Assay systems using the fluorogenic aldehyde were validated by screening of aldol catalysts, ranking of the activities of the catalysts, and evaluation of reaction conditions.
• Design, synthesis and pharmacological characterization of coumarin-based fluorescent analogs of excitatory amino acid transporter subtype 1 selective inhibitors, UCPH-101 and UCPH-102
  作者：Tri H.V. Huynh、Bjarke Abrahamsen、Karsten K. Madsen、Alba Gonzalez-Franquesa、Anders A. Jensen、Lennart Bunch

  DOI：10.1016/j.bmc.2012.09.049

  日期：2012.12

  GLAST), with the analogs UCPH-101 (IC50 = 0.66 μM) and UCPH-102 (IC50 = 0.43 μM) being the most potent inhibitors in the series. In this paper, we present the design, synthesis and pharmacological evaluation of six coumarin-based fluorescent analogs of UCPH-101/102 as subtype-selective inhibitors at EAAT1. Analogs 1114 failed to inhibit EAAT1 function (IC50 values >300 μM), whereas analogs 15 and UCPH-102F

  兴奋性氨基酸转运蛋白（EAAT）在调节哺乳动物中枢神经系统中谷氨酸的突触浓度中起关键作用。迄今为止，已鉴定出五种不同的亚型，在人类中名为EAAT15（在啮齿动物中分别为GLAST，GLT-1，EAAC1，EAAT4和EAAT5）。最近，我们发表并提出了一种新型的EAAT1（和GLAST）选择性抑制剂的结构-活性关系（SAR）研究，其类似物为UCPH-101（IC 50  = 0.66μM ）和UCPH-102（IC 50  = 0.43μM）是该系列中最有效的抑制剂。在本文中，我们介绍了六种基于香豆素的UCPH-101 / 102荧光素类似物作为EAAT1亚型选择性抑制剂的设计，合成和药理学评估。类似物1114未能抑制EAAT1功能（IC 50值> 300μM），而类似物15和UCPH-102F抑制EAAT1，IC 50值处于中等微摩尔范围（分别为17μM和14μM ）。在生理pH下，类似