3-phenyl-1H-pyrano(3,4-c)pyridin-1-one | 5657-55-6

• 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-phenyl-1H-pyrano(3,4-c)pyridin-1-one
• 英文别名: 3-phenyl-7-azaisocoumarin；3-phenyl-pyrano[3,4-c]pyridin-1-one；3-Phenyl-1H-pyrano<3,4-c>-pyridin-1-on；3-Phenylpyrano[3,4-c]pyridin-1-one
• CAS: 5657-55-6
• 化学式: C₁₄H₉NO₂
• 分子量: 223.231
• InChiKey: YMSRDLCFCMPXGQ-UHFFFAOYSA-N

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-phenyl-1H-pyrano(3,4-c)pyridin-1-one 在 氨 作用下， 以 乙二醇甲醚 为溶剂， 以131 mg的产率得到3-phenyl-2,7-naphthyridin-1(2H)-one
  参考文献：
  名称：

  Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2015.05.005
• 作为产物：
  描述：

  4-氯-3-氰基吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 PPA 、 三乙胺 作用下， 反应 6.25h， 生成 3-phenyl-1H-pyrano(3,4-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

• Application of Organolithium and Related Reagents in Synthesis. Part 11¹. Metallation of 2-Methyl- and 4-Methylnicotinic Acids. A Useful Method for Preparation of AZA-Isocoumarins
  作者：J. Epsztajn、M. W. Płotka、J. Ścianowski

  DOI：10.1080/00397919208019305

  日期：1992.5

  Abstract The metallation (LDA/THF) of 2-methyl- and 4-methylnicotinic acids (1) and (2), and the subsequent reaction of the lithiated species (3) and (4) with carbonyl electrophiles as a synthetic route of 5-aza- and 7-aza-isocoumarins (7), (8), (9) and (10), is described. The isocoumarins (9) and (10) appeared to be readily transformable into the corresponding naphthyridines (11) and (12).

  摘要 2-甲基-和 4-甲基烟酸 (1) 和 (2) 的金属化 (LDA/THF)，以及锂化物质 (3) 和 (4) 与羰基亲电试剂的后续反应，作为 5描述了-氮杂-和7-氮杂-异香豆素(7)、(8)、(9)和(10)。异香豆素 (9) 和 (10) 似乎很容易转化为相应的萘啶 (11) 和 (12)。
• Merlini,L. et al., Gazzetta Chimica Italiana, 1975, vol. 105, p. 339 - 348
  作者：Merlini,L. et al.

  DOI：——

  日期：——
• 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：——