2-(3,4-dimethoxyphenyl)-3-phenyl-4H-pyrido[1,2-a]pyrimidine-4-one | 1459205-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(3,4-dimethoxyphenyl)-3-phenyl-4H-pyrido[1,2-a]pyrimidine-4-one
• 英文别名: 2-(3,4-dimethoxyphenyl)-3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-one；2-(3,4-Dimethoxyphenyl)-3-phenylpyrido[1,2-a]pyrimidin-4-one
• CAS: 1459205-56-1
• 化学式: C₂₂H₁₈N₂O₃
• 分子量: 358.397
• InChiKey: HCMITHCVVSIPJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯胺 在 sodium carbonate 、 溶剂红 43 作用下， 以 水 、 乙腈 为溶剂， 反应 25.0h， 生成 2-(3,4-dimethoxyphenyl)-3-phenyl-4H-pyrido[1,2-a]pyrimidine-4-one
  参考文献：
  名称：

  吡啶并[1,2-a]嘧啶-4-酮和噻唑并[3,2-a]嘧啶-5-酮的可见光辅助直接C3-H芳基化

  摘要：

  在温和的反应条件下，开发了使用可见光照射的无金属催化剂、有机染料催化的吡啶并[1,2- a ]嘧啶-4-酮的C3-H芳基化。这种操作简单且直接的C-H功能化方法有效地产生了具有生物学意义的C3芳基化吡啶并[1,2- a ]嘧啶-4-一和噻唑并[3,2- a ]嘧啶-5-一衍生物，包括医学上重要的内皮细胞功能障碍抑制剂和抗炎剂的产率良好至优异，且具有良好的官能团耐受性。目前的光诱导直接 C3-H 芳基化方法适合放大合成。

  DOI：

  10.1021/acs.joc.3c00780

文献信息

• A novel 2,3-diphenyl-4H-pyrido[1,2-a]pyrimidin-4-one derivative inhibits endothelial cell dysfunction and smooth muscle cell proliferation/activation
  作者：Serena Del Turco、Stefania Sartini、Cassandra Sentieri、Chiara Saponaro、Teresa Navarra、Bianca Dario、Federico Da Settimo、Concettina La Motta、Giuseppina Basta

  DOI：10.1016/j.ejmech.2013.11.021

  日期：2014.1

  Hyper-proliferation and migration of vascular smooth muscle cells and endothelial cell dysfunction are central events in the development of neo-intimal lesions.Pursuing our interest in the synthesis of bioisosters of flavonoids, we studied in depth a novel synthetic 2,3-diphenyl-4H-pyrido[1,2-a]pyrimidin-4-one derivative, examining its effects in vitro on induced-cell proliferation and activation in human aortic smooth muscle cells (HAoSMCs) and in human umbilical vein endothelial cells (HUVECs).Compared with two well known flavonoids, apigenin and quercetin, the novel compound, 2-(3,4-dimethoxyphenyl)-3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-one, 3, was not toxic for HUVECs, even at high concentrations and for long incubation times, while the two flavonoids were not tolerated, even at concentrations as low as 10 mu mol/L. Compound 3 inhibited selectively, and in a concentration-dependent manner, the proliferation of HAoSMCs but not that of HUVECs. In HUVECs, it inhibited the cytokine-induced vascular cell adhesion molecule-1 expression, but not the cyclooxygenase-2 (COX-2) expression. Instead, in HAoSMC, it inhibited the induction of COX-2 expression and the relative release of prostaglandin E-2. In addition, it inhibited the transcription of the matrix metalloproteinase-9 and its activity..Thanks to its multiple and tissue-specific function, 2-(3,4-dimethoxyphenyl)-3-phenyl-4H-pyrido[1,2-a]pyrimidin-4-one might replace or assist the action of current drugs eluted by coronary stents, in order to promote a functional repair of damaged wall. (C) 2013 Elsevier Masson SAS. All rights reserved.
• [EN] A THERAPEUTIC AGENT FOR TREATMENT OF BLOOD VESSELS<br/>[FR] AGENT THÉRAPEUTIQUE UTILISABLE EN VUE DU TRAITEMENT DES VAISSEAUX SANGUINS
  申请人：UNIV PISA

  公开号：WO2013144860A1

  公开（公告）日：2013-10-03

  A therapeutic agent for the treatment of blood vessels, preferably applied to coronary stents, characterised in that it comprises compounds with a 2,3-diphenyl-4H- pyrido[1,2-a]pyrimidine-4-one nucleus.