3-(3-methoxyphenyl)-8-methyl-2-oxo-2H-chromene-6-carbaldehyde | 1290078-30-6

• 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: 3-(3-methoxyphenyl)-8-methyl-2-oxo-2H-chromene-6-carbaldehyde
• 英文别名: 3-(3-Methoxyphenyl)-8-methyl-2-oxochromene-6-carbaldehyde；3-(3-methoxyphenyl)-8-methyl-2-oxochromene-6-carbaldehyde
• CAS: 1290078-30-6
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: IEPLPJGCMZZOHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  靛红酸酐 、 3-(3-methoxyphenyl)-8-methyl-2-oxo-2H-chromene-6-carbaldehyde 、 甲胺 在 溶剂黄146 作用下， 以86%的产率得到2-(3-(3-methoxyphenyl)-8-methyl-2-oxo-2H-chromen-6-yl)-3-methyl-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  Discovery of coumarin-dihydroquinazolinone analogs as niacin receptor 1 agonist with in-vivo anti-obesity efficacy

  摘要：

  In this study, we presented rational designing and synthesis of coumarin-dihydroquinazolinone conjugates to evaluate their agonist activity at GPR109a receptor. Among the synthesized small molecule library, compound 10c displayed robust agonist action at GPR109a with EC50 < 11 nM. Homology model of human GPR109a protein was generated to realize the binding interaction of the active molecule with the active site of GPR109a. Further, the efficacy of active compound 10c was supported by in -vivo experiments which showed reduced body weight in diet induced obese mice model. Interestingly, compound 10c reduced leptin in blood plasma and total serum cholesterol. These results suggest that the coumarin-dihydroquinazolinone conjugate is a suitable scaffold to further expand the chemical diversity and make them potential niacin receptor 1 agonist. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.04.037
• 作为产物：
  描述：

  邻甲酚 在 N-甲基吗啉 、 三聚氯氰 、 乌洛托品 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 3-(3-methoxyphenyl)-8-methyl-2-oxo-2H-chromene-6-carbaldehyde
  参考文献：
  名称：

  Discovery of coumarin-dihydroquinazolinone analogs as niacin receptor 1 agonist with in-vivo anti-obesity efficacy

  摘要：

  In this study, we presented rational designing and synthesis of coumarin-dihydroquinazolinone conjugates to evaluate their agonist activity at GPR109a receptor. Among the synthesized small molecule library, compound 10c displayed robust agonist action at GPR109a with EC50 < 11 nM. Homology model of human GPR109a protein was generated to realize the binding interaction of the active molecule with the active site of GPR109a. Further, the efficacy of active compound 10c was supported by in -vivo experiments which showed reduced body weight in diet induced obese mice model. Interestingly, compound 10c reduced leptin in blood plasma and total serum cholesterol. These results suggest that the coumarin-dihydroquinazolinone conjugate is a suitable scaffold to further expand the chemical diversity and make them potential niacin receptor 1 agonist. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.04.037

文献信息

• Efficient and General Synthesis of 3-Aryl Coumarins Using Cyanuric Chloride¹
  作者：Koneni Sashidhara、Gopala Palnati、Srinivasa Avula、Abdhesh Kumar

  DOI：10.1055/s-0031-1290344

  日期：2012.3

  protocol for a rapid synthesis of different substituted 3-aryl coumarins is reported. A series of different substituted phenyl acetic acids have been successfully reacted with different substituted 2-hydroxy benzaldehydes in the presence of cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) and N-methyl morpholine to afford 3-aryl coumarins in good to excellent yields. synthesis - 3-aryl coumarins -

  报道了快速合成不同取代的3-芳基香豆素的有效且通用的方案。在氰尿酰氯（2,4,6-三氯-1,3,5-三嗪）和N-甲基吗啉的存在下，一系列不同的取代苯基乙酸已成功与不同的取代的2-羟基苯甲醛反应，得到3芳基香豆素的收率高至优异。 合成-3-芳基香豆素-氰尿酰氯-2-羟基苯甲醛 系列“新型合成方法论研究”的第八部分。
• Discovery of coumarin-dihydroquinazolinone analogs as niacin receptor 1 agonist with in-vivo anti-obesity efficacy
  作者：L. Ravithej Singh、Ajeet Kumar、Akanksha Upadhyay、Sampa Gupta、Gopala Reddy Palanati、Kamakshi Sikka、Mohammad Imran Siddiqi、Prem N. Yadav、Koneni V. Sashidhara

  DOI：10.1016/j.ejmech.2018.04.037

  日期：2018.5

  In this study, we presented rational designing and synthesis of coumarin-dihydroquinazolinone conjugates to evaluate their agonist activity at GPR109a receptor. Among the synthesized small molecule library, compound 10c displayed robust agonist action at GPR109a with EC50 < 11 nM. Homology model of human GPR109a protein was generated to realize the binding interaction of the active molecule with the active site of GPR109a. Further, the efficacy of active compound 10c was supported by in -vivo experiments which showed reduced body weight in diet induced obese mice model. Interestingly, compound 10c reduced leptin in blood plasma and total serum cholesterol. These results suggest that the coumarin-dihydroquinazolinone conjugate is a suitable scaffold to further expand the chemical diversity and make them potential niacin receptor 1 agonist. (C) 2018 Elsevier Masson SAS. All rights reserved.