3-methyl-2-(8-methyl-2-oxo-3-p-tolyl-2H-chromen-6-yl)-2,3-dihydroquinazolin-4(1H)-one | 1476068-40-2

• 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-methyl-2-(8-methyl-2-oxo-3-p-tolyl-2H-chromen-6-yl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 3-Methyl-2-[8-methyl-3-(4-methylphenyl)-2-oxochromen-6-yl]-1,2-dihydroquinazolin-4-one；3-methyl-2-[8-methyl-3-(4-methylphenyl)-2-oxochromen-6-yl]-1,2-dihydroquinazolin-4-one
• CAS: 1476068-40-2
• 化学式: C₂₆H₂₂N₂O₃
• 分子量: 410.472
• InChiKey: CAUFJROIYYUVQC-UHFFFAOYSA-N

物化性质

• 熔点：
  238-240 °C
• 沸点：
  659.3±55.0 °C(predicted)
• 密度：
  1.257±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  靛红酸酐 在 N-甲基吗啉 、 三聚氯氰 、 ammonium acetate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3-methyl-2-(8-methyl-2-oxo-3-p-tolyl-2H-chromen-6-yl)-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  咪唑和 2,3-二氢喹唑啉酮衍生物的一锅区域选择性合成 - 轻松获得“类天然分子”；系列中的第十三部分：“新型合成方法研究”

  摘要：

  报道了一种温和且高度实用的区域选择性合成咪唑和 2,3-二氢喹唑啉酮衍生物，由 5-烷基-4-羟基间苯二醛与合适的底物在乙酸中合成。2,3-二氢喹唑啉酮的分子多样性的进一步探索通过多种药理学相关的天然产物样支架的合成得到证明。

  DOI：

  10.1055/s-0033-1339466

文献信息

• 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.
• One-Pot Regioselective Synthesis of Imidazole and 2,3-Dihydroquinazolinone Derivatives - An Easy Access to ‘Nature-Like Molecules'; Part XIII in the Series: ‘Studies on Novel Synthetic Methodologies'
  作者：Koneni Sashidhara、Gopala Palnati、Ranga Dodda、Srinivasa Avula、Priyanka Swami

  DOI：10.1055/s-0033-1339466

  日期：——

  A mild and highly practical regioselective synthesis of imidazole and 2,3-dihydroquinazolinone derivatives from 5-alkyl-4-hydroxyisophthalaldehydes with suitable substrates in acetic acid is reported. Further exploration of the molecular diversity of 2,3-dihydroquinazolinone is demonstrated by the synthesis of diverse pharmacologically relevant natural-product-like scaffolds.

  报道了一种温和且高度实用的区域选择性合成咪唑和 2,3-二氢喹唑啉酮衍生物，由 5-烷基-4-羟基间苯二醛与合适的底物在乙酸中合成。2,3-二氢喹唑啉酮的分子多样性的进一步探索通过多种药理学相关的天然产物样支架的合成得到证明。