3-甲氧基-8-甲基-2-苯基色烯-4-酮 | 87165-68-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 3-甲氧基-8-甲基-2-苯基色烯-4-酮
• 英文名称: 3-methoxy-8-methyl-2-phenylchromen-4-one
• 英文别名: 3-Methoxy-8-methyl-2-phenyl-4H-1-benzopyran-4-one
• CAS: 87165-68-2
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: SCMWGCOMUAAIGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-甲氧基-8-甲基-2-苯基色烯-4-酮 在 N-溴代丁二酰亚胺(NBS) 、 乌洛托品 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 9.0h， 生成 3-methoxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde
  参考文献：
  名称：

  1,4-Dihydropyridine derivatives as calcium channel modulators: the role of 3-methoxy-flavone moiety

  摘要：

  It was earlier recognized that calcium antagonists, and in particular 1,4-dihydropyridines, exhibited distinct cardiovascular profiles. In addition two different splice variants of the L-type calcium channel were found in vascular and cardiac tissues. In this study, novel substituted 1,4-dihydropyridines with a 3-methoxy-flavone moiety were synthesized and structural modifications of the substituents in the dihydropyridine ring of nifedipine were carried out in order to find tissue specific compounds. The negative inotropic, chronotropic and vasorelaxant effects were investigated on guinea-pig left, right atria and aortic strips, respectively. The introduction of an heteroaromatic ring in 4-position of the 1,4-dihydropyridine nucleus led to compounds selective for cardiac tissues. Moreover, different residues in the 1,4-dihydropyridine ring could modulate the chronotropic versus inotropic activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.007
• 作为产物：
  描述：

  3-羟基-8-甲基-2-苯基色烯-4-酮 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以96%的产率得到3-甲氧基-8-甲基-2-苯基色烯-4-酮
  参考文献：
  名称：

  1,4-Dihydropyridine derivatives as calcium channel modulators: the role of 3-methoxy-flavone moiety

  摘要：

  It was earlier recognized that calcium antagonists, and in particular 1,4-dihydropyridines, exhibited distinct cardiovascular profiles. In addition two different splice variants of the L-type calcium channel were found in vascular and cardiac tissues. In this study, novel substituted 1,4-dihydropyridines with a 3-methoxy-flavone moiety were synthesized and structural modifications of the substituents in the dihydropyridine ring of nifedipine were carried out in order to find tissue specific compounds. The negative inotropic, chronotropic and vasorelaxant effects were investigated on guinea-pig left, right atria and aortic strips, respectively. The introduction of an heteroaromatic ring in 4-position of the 1,4-dihydropyridine nucleus led to compounds selective for cardiac tissues. Moreover, different residues in the 1,4-dihydropyridine ring could modulate the chronotropic versus inotropic activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.007

文献信息

• HYDROXYFLAVONE DERIVATIVES AS TAU PROTEIN KINASE 1 INHIBITORS
  申请人：MITSUBISHI CHEMICAL CORPORATION

  公开号：EP1115718A1

  公开（公告）日：2001-07-18
• [EN] HYDROXYFLAVONE DERIVATIVES AS TAU PROTEIN KINASE 1 INHIBITORS<br/>[FR] DERIVES D'HYDROXYFLAVONE UTILISES COMME INHIBITEURS DE TAU-PROTEINE-KINASE 1
  申请人：MITSUBISHI CHEM CORP

  公开号：WO2000017184A1

  公开（公告）日：2000-03-30

  A medicament for preventive and/or therapeutic treatment of a disease caused by tau protein kinase 1 hyperactivity or a neurodegenerative disease which comprises as an active ingredient a substance selected from the group consisting of a hydroxyflavone derivative represented by formula (I) and a salt thereof, and a solvate thereof and a hydrate thereof, wherein R1 represents hydrogen atom or hydroxyl group; R2 represents hydrogen atom or a C¿1?-C18 alkyl group which may have one or more C6-C14 aryl groups; and Ar represents a C6-C14 aryl group which may be substituted or an aromatic heterocyclic group which may be substituted.
• 1,4-Dihydropyridine derivatives as calcium channel modulators: the role of 3-methoxy-flavone moiety
  作者：Roberta Budriesi、Alessandra Bisi、Pierfranco Ioan、Angela Rampa、Silvia Gobbi、Federica Belluti、Lorna Piazzi、Piero Valenti、Alberto Chiarini

  DOI：10.1016/j.bmc.2005.03.007

  日期：2005.5

  It was earlier recognized that calcium antagonists, and in particular 1,4-dihydropyridines, exhibited distinct cardiovascular profiles. In addition two different splice variants of the L-type calcium channel were found in vascular and cardiac tissues. In this study, novel substituted 1,4-dihydropyridines with a 3-methoxy-flavone moiety were synthesized and structural modifications of the substituents in the dihydropyridine ring of nifedipine were carried out in order to find tissue specific compounds. The negative inotropic, chronotropic and vasorelaxant effects were investigated on guinea-pig left, right atria and aortic strips, respectively. The introduction of an heteroaromatic ring in 4-position of the 1,4-dihydropyridine nucleus led to compounds selective for cardiac tissues. Moreover, different residues in the 1,4-dihydropyridine ring could modulate the chronotropic versus inotropic activity. (c) 2005 Elsevier Ltd. All rights reserved.