3-Phenylpyrano[4,3-c]pyridin-1-one | 118160-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-Phenylpyrano[4,3-c]pyridin-1-one
• 英文别名: 3-Phenyl-1H-pyrano[4,3-c]pyridin-1-one
• CAS: 118160-04-6
• 化学式: C₁₄H₉NO₂
• 分子量: 223.231
• InChiKey: FVJSGLJBLDWPPB-UHFFFAOYSA-N

物化性质

• 熔点：
  166-168 °C(Solv: isopropyl ether (108-20-3); hexane (110-54-3))
• 沸点：
  407.4±45.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 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：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Phenylpyrano[4,3-c]pyridin-1-one 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 3-(2-oxo-2-phenylethyl)-4-pyridinecarboxylic acid
  参考文献：
  名称：

  α-（3-吡啶基）丙二酸酯：制备与合成应用

  摘要：

  芳环的烷基化是有机合成中的主要挑战，因为可以构建更复杂的碳骨架。据报道，通过丙二酸酯将3-硝基-4-吡啶基甲酸甲酯（1）中的硝基进行亲核芳香取代，使吡啶烷基化。α-（3-吡啶基）丙二酸酯产物（3）的多功能性通过许多新的3-烷基化吡啶和新的稠合双杂环的形成来证明。选择性地制备出顺式2-卤甲基-4-（3-吡啶基）四氢呋喃产物。通过一系列NMR实验，获得了几乎所有产品的精确1 H和13 C NMR赋值。

  DOI：

  10.1016/j.tet.2007.09.026
• 作为产物：
  描述：

  3-氯-4-氰基吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 PPA 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.25h， 生成 3-Phenylpyrano[4,3-c]pyridin-1-one
  参考文献：
  名称：

  Sakamoto, Takao; An-Naka, Masayuki; Kondo, Yoshinori, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 5, p. 1890 - 1894

  摘要：

  DOI：

文献信息

• Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases
  作者：Katerina Kumpan、Amit Nathubhai、Chenlu Zhang、Pauline J. Wood、Matthew D. Lloyd、Andrew S. Thompson、Teemu Haikarainen、Lari Lehtiö、Michael D. Threadgill

  DOI：10.1016/j.bmc.2015.05.005

  日期：2015.7

  The tankyrases are members of the PARP superfamily; they poly(ADP-ribosyl) ate their target proteins using NAD(+) as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrases (TRF1, NuMA and axin) are involved in replication of cancer cells; thus inhibitors of the tankyrases may have anticancer activity. Using structure-based drug design and by analogy with known 3-arylisoquinolin-1-one and 2-arylquinazolin-4-one inhibitors, series of arylnaphthyridinones, arylpyridinopyrimidinones and their tetrahydro-derivatives were synthesised and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-ones, 3-aryl-2,6-naphthyridin-1-ones and 3-aryl-2,7-naphthyridin-1-ones were prepared by acid-catalysed cyclisation of the corresponding arylethynylpyridinenitriles or reaction of bromopyridinecarboxylic acids with beta-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. Cu-catalysed reaction of benzamidines with bromopyridinecarboxylic acids furnished 2-arylpyrido[2,3-d]pyrimidin-4-ones. Condensation of benzamidines with methyl 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d] pyrimidin-4-ones, aza analogues of the known inhibitor XAV939. Introduction of the ring-N in the arylnaphthyridinones and the arylpyridopyrimidinones caused > 1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogues. However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrases, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 versus tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2. (C) 2015 Elsevier Ltd. All rights reserved.
• SAKAMOTO, TAKAO;AN-NAKA, MASAYUKI;KONDO, YOSHINORI;ARAKI, TOMIO;YAMANAKA,+, CHEM. AND PHARM. BULL., 36,(1988) N 5, 1890-1894
  作者：SAKAMOTO, TAKAO、AN-NAKA, MASAYUKI、KONDO, YOSHINORI、ARAKI, TOMIO、YAMANAKA,+

  DOI：——

  日期：——