1-(5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-yl)-3-(pyridin-3-yl)propan-1-one | 1588827-97-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-yl)-3-(pyridin-3-yl)propan-1-one
• 英文别名: 1-[5-Hydroxy-2-methyl-2-(4-methylpent-3-enyl)chromen-6-yl]-3-pyridin-3-ylpropan-1-one；1-[5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)chromen-6-yl]-3-pyridin-3-ylpropan-1-one
• CAS: 1588827-97-7
• 化学式: C₂₄H₂₇NO₃
• 分子量: 377.483
• InChiKey: YNXUCCSUUYRDJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[5-hydroxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl]-3-pyridin-3-ylpropenone 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以60%的产率得到1-(5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-yl)-3-(pyridin-3-yl)propan-1-one
  参考文献：
  名称：

  Synthesis, Structure–Activity Relationships, and Biological Studies of Chromenochalcones as Potential Antileishmanial Agents

  摘要：

  Antileishmanial activities of a library of synthetic chalcone analogues have been examined. Among them, five compounds (11, 14, 16, 17, 22, and 24) exhibited better activity than the marketed drug miltefosine in in vitro studies against the intracellular amastigotes form of Leishmania donovani. Three promising compounds, 16, 17, and 22, were tested in a L. donovani/hamster model. Oral administration of chalcone 16, at a concentration of 100 mg/kg of body weight per day for 5 consecutive days, resulted in >84% parasite inhibition at day 7 post-treatment and it retained the activity until day 28. The molecular and immunological studies revealed that compound 16 has a dual nature to act as a direct parasite killing agent and as a host immunostimulant. Pharmacokinetics and serum albumin binding studies also suggest that compound 16 has the potential to be a candidate for the treatment of the nonhealing form of leishmaniasis.

  DOI：

  10.1021/jm401893j