3-(4-chlorophenyl)-4H-pyrido[1,2-a]pyrimidin-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 3-(4-chlorophenyl)-4H-pyrido[1,2-a]pyrimidin-4-one
• 英文别名: 3-(4-Chlorophenyl)pyrido[1,2-a]pyrimidin-4-one；3-(4-chlorophenyl)pyrido[1,2-a]pyrimidin-4-one
• 化学式: C₁₄H₉ClN₂O
• 分子量: 256.691
• InChiKey: BOPWDUPMEAXROP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 3-(4-chlorophenyl)-4H-pyrido[1,2-a]pyrimidin-4-one
  参考文献：
  名称：

  芳基取代稠合嘧啶酮的简便一锅法合成

  摘要：

  摘要 合成了一系列具有良好生物活性的3-苯基吡啶并[1,2-a]嘧啶酮4、3-苯基嘧啶并[1,2-c]喹唑啉酮7和3-苯基吡嗪并[1,2-a]嘧啶酮10。被表达。

  DOI：

  10.1515/hc-2015-0262

文献信息

• Pd-Catalyzed Ag(I)-Promoted C3-Arylation of Pyrido[1,2-<i>a</i>]pyrimidin-4-ones with Bromo/Iodo-Arenes
  作者：Sankar K. Guchhait、Garima Priyadarshani

  DOI：10.1021/acs.joc.5b01573

  日期：2015.8.21

  A regioselective Ag(I)-promoted Pd-catalyzed C3-H activation arylation of pyrido[1,2-a]pyrimidin-4-ones with bromo/iodo-(hetero)arenes under aqueous conditions has been developed. It affords an efficient access to pharmaceutically important versatile 3-arylpyrido[1,2-a]pyrimidin-4-ones. Interestingly, the arylation undergoes via a pathway with an unusual feature involving the formation of cationic arylpalladium species promoted by halo-sequestering Ag salts enabling concerted C3-palladation-deprotonation, as explored by relevant experiments and spectroscopic studies. The present approach is step economical, good yielding, and compatible with various functionalities and applicable to a wide range of starting materials.
• Scaffold-hopping of bioactive flavonoids: Discovery of aryl-pyridopyrimidinones as potent anticancer agents that inhibit catalytic role of topoisomerase IIα
  作者：Garima Priyadarshani、Suyog Amrutkar、Anmada Nayak、Uttam C. Banerjee、Chanakya N. Kundu、Sankar K. Guchhait

  DOI：10.1016/j.ejmech.2016.06.024

  日期：2016.10

  A strategy of scaffold-hopping of bioactive natural products, flavones and isofl avones, leading to target-based discovery of potent anticancer agents has been reported for the first time. Scaffold-hopped flavones, 2-aryl-4H-pyrido[1,2-a]pyrimidin-4-ones and the scaffold-hopped isofiavones, 3-aryl-pyrido[1,2-a]pyrimidin-4-ones were synthesized via Pd-catalyzed activation-arylation methods. Most of the compounds were found to exhibit pronounced human topoisomerase II alpha (hTopoll alpha) inhibitory activities and several compounds were found to be more potent than etoposide (a hTopoll alpha-inhibiting anticancer drug). These classes of compounds were found to be hTopoll alpha-selective catalytic inhibitors while not interfering with topoisomerase I and interacted with DNA plausibly in groove domain. Cytotoxicities against various cancer cells, low toxicity in normal cells, and apoptotic effects were observed. Interestingly, compared to parent flavones/isoflavones, their scaffold-hopped analogs bearing alike functionalities showed significant/enhanced hTopoII alpha-inhibitory and cytotoxic properties, indicating the importance of a natural product-based scaffold-hopping strategy in the drug discovery. (C) 2016 Elsevier Masson SAS. All rights reserved.
• A facile one-pot synthesis of aryl-substituted fused pyrimidinones
  作者：Hyuck Joo Lee、Yang-Heon Song

  DOI：10.1515/hc-2015-0262

  日期：2016.4.1

  Abstract The convenient synthesis of a series of 3-phenylpyrido[1,2-a]pyrimidinones 4, 3-phenylpyrimido[1,2-c]quinazolinones 7 and 3-phenylpyrazino[1,2-a]pyrimidinones 10 with promising biological activity is presented.

  摘要 合成了一系列具有良好生物活性的3-苯基吡啶并[1,2-a]嘧啶酮4、3-苯基嘧啶并[1,2-c]喹唑啉酮7和3-苯基吡嗪并[1,2-a]嘧啶酮10。被表达。