8-bromo-6-methyl-3-phenylcoumarin | 1247212-14-1

• 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: 8-bromo-6-methyl-3-phenylcoumarin
• 英文别名: 8-bromo-6-methyl-3-phenylchromen-2-one
• CAS: 1247212-14-1
• 化学式: C₁₆H₁₁BrO₂
• 分子量: 315.166
• InChiKey: TYLXEMSZGAPZTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙酸 、 3-溴-2-羟基-5-甲基苯甲醛 在 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以45%的产率得到8-bromo-6-methyl-3-phenylcoumarin
  参考文献：
  名称：

  New halogenated 3-phenylcoumarins as potent and selective MAO-B inhibitors

  摘要：

  With the aim to find out the structural features for the MAO inhibitory activity and selectivity, in the present communication we report the synthesis and pharmacological evaluation of a new series of bromo-6-methyl-3-phenylcoumarin derivatives (with bromo atom in both different benzene rings of the skeleton) with and without different number of methoxy substituent at the 3-phenyl ring. The methoxy substituents were introduced, in this new scaffold, in the meta and/or para positions of the 3-phenyl ring. The synthesized compounds 3-7 were evaluated as MAO-A and B inhibitors using R-(-)-deprenyl (selegiline) and iproniazide as reference inhibitors, showing, most of them, MAO-B inhibitory activities in the low nanomolar range. Compounds 4 (IC50 = 11.05 nM), 5 (IC50 = 3.23 nM) and 6 (IC50 = 7.12 nM) show higher activity than selegiline (IC50 = 19.60 nM) and higher MAO-B selectivity, with more than 9050-fold, 30,960-fold and 14,045-fold inhibition levels, with respect to the MAO-A isoform. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.013

文献信息

• [EN] LABELLED COUMARIN DERIVATIVES<br/>[FR] DÉRIVÉS DE COUMARINE MARQUÉS
  申请人：GE HEALTHCARE LTD

  公开号：WO2016097339A1

  公开（公告）日：2016-06-23

  The present invention relates to compounds having selective binding for MAO-B as compared with MAO-A. The invention also provides radioactive versions of these compounds, and precursor compounds for the synthesis of these radioactive compounds. The radioactive compounds of the invention can find use for in vivo imaging applications.

  本发明涉及与MAO-A相比具有选择性结合MAO-B的化合物。该发明还提供这些化合物的放射性版本，以及用于合成这些放射性化合物的前体化合物。本发明的放射性化合物可用于体内成像应用。
• [EN] MONOAMINE OXIDASE B BINDERS FOR USE IN THE TREATMENT AND THE DIAGNOSTIC OF ALZHEIMER DISEASE<br/>[FR] LIANTS DE TYPE MONOAMINE OXYDASE B POUR LEUR UTILISATION DANS LE TRAITEMENT ET LE DIAGNOSTIC DE LA MALADIE D'ALZHEIMER
  申请人：CLINO LTD

  公开号：WO2017103257A1

  公开（公告）日：2017-06-22

  The present invention provides methods useful in the management neuropathological conditions where expression of monoamine oxidase B (MAO-B) deviates from that seen in healthy subjects. The invention provides for the use of compounds in therapeutic and diagnostic applications.
• New halogenated 3-phenylcoumarins as potent and selective MAO-B inhibitors
  作者：Maria João Matos、Dolores Viña、Patricia Janeiro、Fernanda Borges、Lourdes Santana、Eugenio Uriarte

  DOI：10.1016/j.bmcl.2010.07.013

  日期：2010.9

  With the aim to find out the structural features for the MAO inhibitory activity and selectivity, in the present communication we report the synthesis and pharmacological evaluation of a new series of bromo-6-methyl-3-phenylcoumarin derivatives (with bromo atom in both different benzene rings of the skeleton) with and without different number of methoxy substituent at the 3-phenyl ring. The methoxy substituents were introduced, in this new scaffold, in the meta and/or para positions of the 3-phenyl ring. The synthesized compounds 3-7 were evaluated as MAO-A and B inhibitors using R-(-)-deprenyl (selegiline) and iproniazide as reference inhibitors, showing, most of them, MAO-B inhibitory activities in the low nanomolar range. Compounds 4 (IC50 = 11.05 nM), 5 (IC50 = 3.23 nM) and 6 (IC50 = 7.12 nM) show higher activity than selegiline (IC50 = 19.60 nM) and higher MAO-B selectivity, with more than 9050-fold, 30,960-fold and 14,045-fold inhibition levels, with respect to the MAO-A isoform. (C) 2010 Elsevier Ltd. All rights reserved.