6,8-dibromo-N-tert-butyl-2-oxo-2H-chromene-3-carboxamide | 886133-38-6

• 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: 6,8-dibromo-N-tert-butyl-2-oxo-2H-chromene-3-carboxamide
• 英文别名: 6,8-dibromo-N-tert-butyl-2-oxochromene-3-carboxamide
• CAS: 886133-38-6
• 化学式: C₁₄H₁₃Br₂NO₃
• 分子量: 403.07
• InChiKey: YQHUCPNDZXMPSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6,8-二溴-2-氧代-2H-色烯-3-羧酸乙酯 在 盐酸 、 4-二甲氨基吡啶 、 氯化亚砜 、 sodium hydroxide 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 6,8-dibromo-N-tert-butyl-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  New 2H-chromene-3-carboxamide derivatives: Design, synthesis and use as inhibitors of hMAO

  摘要：

  A series new 2H-chromene-3-carboxamide derivatives 4a-4t were synthesized and evaluated as monoamine oxidase A and B (MAO-A and MAO-B) inhibitors. Among them, compound 4d (IC50 = 0.93 μM, IC(50 iproniazid) = 7.80 μM) showed the most activity and higher MAO-B selectivity (64.5-fold vs. 1-fold) with respect to the MAO-A isoform. The active compound 4d was also docked into the hMAO-B complex structure active site to determine the probable binding model. The results indicated that conserved residue CYSA 172 was important for ligand binding via hydrogen bond interaction, Pi-Pi interaction was found between the benzene-ring of compound 4d and residue ILEA 199.

  DOI：

  10.1016/j.ejmech.2014.04.060

文献信息

• New 2H-chromene-3-carboxamide derivatives: Design, synthesis and use as inhibitors of hMAO
  作者：Zhi-Xiang Pan、Xu He、Yan-Yan Chen、Wen-Jian Tang、Jing-Bo Shi、Yu-Lan Tang、Bao-An Song、Jun Li、Xin-Hua Liu

  DOI：10.1016/j.ejmech.2014.04.060

  日期：2014.6

  A series new 2H-chromene-3-carboxamide derivatives 4a-4t were synthesized and evaluated as monoamine oxidase A and B (MAO-A and MAO-B) inhibitors. Among them, compound 4d (IC50 = 0.93 μM, IC(50 iproniazid) = 7.80 μM) showed the most activity and higher MAO-B selectivity (64.5-fold vs. 1-fold) with respect to the MAO-A isoform. The active compound 4d was also docked into the hMAO-B complex structure active site to determine the probable binding model. The results indicated that conserved residue CYSA 172 was important for ligand binding via hydrogen bond interaction, Pi-Pi interaction was found between the benzene-ring of compound 4d and residue ILEA 199.