7-{[(E)-3-(5,5-dimethyl-4-oxo-4,5-dihydro-2-furanyl)-2-propenyl]oxy}-4-methyl-2H-chromen-2-one

• 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: 7-{[(E)-3-(5,5-dimethyl-4-oxo-4,5-dihydro-2-furanyl)-2-propenyl]oxy}-4-methyl-2H-chromen-2-one
• 英文别名: 7-[(E)-3-(5,5-dimethyl-4-oxofuran-2-yl)prop-2-enoxy]-4-methylchromen-2-one
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: AXIRQRZVUWCTCT-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙醛,[(4-甲基-2-羰基-2H-1-苯并吡喃-7-基)氧代]- 在 甲基磺酰氯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 7-{[(E)-3-(5,5-dimethyl-4-oxo-4,5-dihydro-2-furanyl)-2-propenyl]oxy}-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Natural and synthetic geiparvarins are strong and selective MAO-B inhibitors. synthesis and SAR studies

  摘要：

  Natural geiparvarin 1 and a number of its analogues were prepared and tested as inhibitors of both monoamine oxidase isoforms, MAO-B and MAO-A. The desmethyl congener 6 of geiparvarin, proved potent and selective MAO-B inhibitor (PIC50 = 7.55 vs 4.62). X-ray crystallography and molecular modelling studies helped the understanding of the observed structure-activity relationships. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00798-9

文献信息

• New geiparvarin analogues from 7-(2-oxoethoxy)coumarins as efficient in vitro antitumoral agents
  作者：Stefano Chimichi、Marco Boccalini、Barbara Cosimelli、Giampietro Viola、Daniela Vedaldi、Francesco Dall'Acqua

  DOI：10.1016/s0040-4039(02)01798-7

  日期：2002.10

  A new class of compounds analogues of geiparvarin is described: aldolic condensation of 3(2H)-furanones and 7-(2-oxoethoxy)coumarins followed by a very efficient dehydration protocol led to the title compounds which show good antitumoral activity against several human cell lines.

  描述了一种新的盖帕瓦林类似物的化合物类似物：3（2 H）-呋喃酮和7-（2-氧代乙氧基）香豆素的醛缩合反应，然后通过非常有效的脱水步骤，可得到标题化合物，该化合物显示出对几种人的良好抗肿瘤活性细胞系。
• Natural and synthetic geiparvarins are strong and selective MAO-B inhibitors. synthesis and SAR studies
  作者：Angelo Carotti、Antonio Carrieri、Stefano Chimichi、Marco Boccalini、Barbara Cosimelli、Carmela Gnerre、Andrea Carotti、Pierre-Alain Carrupt、Bernard Testa

  DOI：10.1016/s0960-894x(02)00798-9

  日期：2002.12

  Natural geiparvarin 1 and a number of its analogues were prepared and tested as inhibitors of both monoamine oxidase isoforms, MAO-B and MAO-A. The desmethyl congener 6 of geiparvarin, proved potent and selective MAO-B inhibitor (PIC50 = 7.55 vs 4.62). X-ray crystallography and molecular modelling studies helped the understanding of the observed structure-activity relationships. (C) 2002 Elsevier Science Ltd. All rights reserved.