3-(4-(trifluoromethyl)phenyl)-4H-pyrido[1,2-a]pyrimidin-4-one | 1335239-86-5

• 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: 3-(4-(trifluoromethyl)phenyl)-4H-pyrido[1,2-a]pyrimidin-4-one
• 英文别名: 3-(p-(Trifluoromethyl)phenyl)-4H-pyrido[1,2-a]pyrimidine-4-one；3-[4-(trifluoromethyl)phenyl]pyrido[1,2-a]pyrimidin-4-one
• CAS: 1335239-86-5
• 化学式: C₁₅H₉F₃N₂O
• 分子量: 290.244
• InChiKey: MSTJINQMPCOTFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4H-吡啶并[1,2-a]嘧啶-4-酮 、 对溴三氟甲苯 在 palladium diacetate 、 potassium carbonate 、 silver carbonate 、 三环己基膦 、 三甲基乙酸 作用下， 以 水 、 甲苯 为溶剂， 以68%的产率得到3-(4-(trifluoromethyl)phenyl)-4H-pyrido[1,2-a]pyrimidin-4-one
  参考文献：
  名称：

  Pd-Catalyzed Ag(I)-Promoted C3-Arylation of Pyrido[1,2-a]pyrimidin-4-ones with Bromo/Iodo-Arenes

  摘要：

  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.

  DOI：

  10.1021/acs.joc.5b01573

文献信息

• Suzuki–Miyaura cross-coupling reactions of halo derivatives of 4H-pyrido[1,2-a]pyrimidin-4-ones
  作者：Annamária Molnár、Anita Kapros、László Párkányi、Zoltán Mucsi、Gábor Vlád、István Hermecz

  DOI：10.1039/c1ob05505d

  日期：——

  cross-coupling reactions of halo derivatives of 4H-pyrido[1,2-a]pyrimidin-4-one with (het)arylboronic acids allow easy access to (het)aryl and vinyl derivatives of this bicycle in good to excellent yields, even from chloro derivatives. The sequence of reactivity of the halogen in the different positions of the ring system was also investigated. 6-Phenyl-4H-pyrido[1,2-a]pyrimidin-4-one could be prepared by thermal

  钯催化的卤素衍生物的Suzuki-Miyaura交叉偶联反应 4 H-吡啶并[1,2- a ]嘧啶-4-一与（杂）芳基硼酸一起使用，即使从氯代衍生物中也可以很容易地获得该自行车的（杂）芳基和乙烯基衍生物。还研究了卤素在环系统不同位置的反应顺序。6-苯基-4 H-吡啶并[1,2- a ]嘧啶-4-一 可以通过热环化制备 异亚丙基（6-苯基吡啶-2-基氨基）亚甲基丙二酸酯，以及少量的7-苯基-1,4-二氢-1,8-萘啶-4-酮。
• 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.