-2 chromanone | 77763-59-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: -2 chromanone
• 英文别名: (E)-3-[(pyridin-2-yl)methylene]chroman-4-one；(pyridinylydene-2')-2 chromanone；(3E)-3-(pyridin-2-ylmethylidene)chromen-4-one
• CAS: 77763-59-8
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: DUDLXRUHPVUQFY-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  -2 chromanone 在 钾硼氢 作用下， 以 甲醇 为溶剂， 生成 -2 chromanol
  参考文献：
  名称：

  Fournier; Berthelot; Pavard, European Journal of Medicinal Chemistry, 1981, vol. 16, # 1, p. 48 - 58

  摘要：

  DOI：
• 作为产物：
  描述：

  吡啶-2-甲醛 、 2,3-二氢苯并吡喃-4-酮 在 potassium alcoholate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以51%的产率得到-2 chromanone
  参考文献：
  名称：

  Fournier; Berthelot; Pavard, European Journal of Medicinal Chemistry, 1981, vol. 16, # 1, p. 48 - 58

  摘要：

  DOI：

文献信息

• Facile synthesis of spiro chromanone-tetrahydrothiophenes with three contiguous stereocenters via sulfa-Michael/aldol cascade reactions
  作者：Ya-Jian Hu、Xiao-Bing Wang、Su-Yi Li、Sai-Sai Xie、Kelvin D.G. Wang、Ling-Yi Kong

  DOI：10.1016/j.tetlet.2014.11.026

  日期：2015.1

  A novel sulfa-Michael/aldol cascade reaction of (E)-3-arylidenechroman-4-ones with 1,4-dithiane-2,5-diol has been developed. This method provides a new practical and facile approach to 4′-hydroxy-2′-aryl-4′,5′-dihydro-2′H-spiro[chroman-3,3′-thiophen]-4-ones with three contiguous stereocenters in high yields. The transformation is atom-economic with good to excellent diastereoselectivities.

  （E）-3-芳基苯并二氢吡喃-4-酮与1，4-二噻吩-2，5-二醇的新型磺胺-迈克尔/羟醛级联反应已得到开发。此方法提供了一种新的实用的和容易的方法来4'-羟基-2'-芳基-4'，5'-二氢-2' ħ -螺[色满-3,3'-噻吩] -4-酮用三个连续高产量的立体中心。该转化是原子经济的，具有良好的至优异的非对映选择性。
• ( E )-3-Heteroarylidenechroman-4-ones as potent and selective monoamine oxidase-B inhibitors
  作者：Nicoletta Desideri、Luca Proietti Monaco、Rossella Fioravanti、Mariangela Biava、Matilde Yáñez、Stefano Alcaro、Francesco Ortuso

  DOI：10.1016/j.ejmech.2016.03.081

  日期：2016.7

  A series of (E)-3-heteroarylidenechroman-4-ones (1a-r) was designed, synthesized and investigated in vitro for their ability to inhibit the enzymatic activity of both human monoamine oxidase (hMAO) isoforms, hMAO-A and hMAO-B. All the compounds were found to be selective hMAO-B inhibitors showing IC50 values in the nanomolar or micromolar range. (E)-5,7-Dichloro-3-[(2-(dimethylamino) pyrimidin-5-yl]methylene}chroman-4-one (1c) was the most interesting compound identified in this study, endowed with higher hMAO-B potency (IC50 = 10.58 nM) and selectivity (SI > 9452) with respect to the reference selective inhibitor selegiline (IC50 = 19.60 nM, IC50 > 3431). Molecular modelling studies were performed for rationalizing at molecular level the target selective inhibition of our compounds, revealing a remarkable contribution of hydrogen bond network and water solvent. (C) 2016 Elsevier Masson SAS. All rights reserved.
• FOURNIER F.; BERTHELOT J.; PAVARD A.-M.; RONZANI N.; BASSELIER J.-J., EUR. J. MED. CHEM.-CHIM. THER., 1981, 16, NO 1, 48-58
  作者：FOURNIER F.、 BERTHELOT J.、 PAVARD A.-M.、 RONZANI N.、 BASSELIER J.-J.

  DOI：——

  日期：——