3-cyano-2-phenylethynylpyridine | 118159-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-cyano-2-phenylethynylpyridine
• 英文别名: 2-(2-Phenylethynyl)pyridine-3-carbonitrile
• CAS: 118159-94-7
• 化学式: C₁₄H₈N₂
• 分子量: 204.231
• InChiKey: QAAKRNUQGPIYNY-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C(Solv: isopropyl ether (108-20-3); hexane (110-54-3))
• 沸点：
  399.6±27.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-cyano-2-phenylethynylpyridine 在 硫酸 、 氨 作用下， 以 水 、 乙二醇甲醚 为溶剂， 反应 1.0h， 以75%的产率得到7-phenyl-1,6-naphthyridin-5-one
  参考文献：
  名称：

  [EN] TANKYRASE INHIBITORS
  [FR] INHIBITEURS DE TANKYRASE

  摘要：

  本发明涉及一种具有式I的化合物，其中X为C(R6)或N，Y为C或N，环A、环B、R1和R2具有本文中定义的含义，前提是当环B为碳环时，X为C(R6)；或其药学上可接受的盐或溶剂。这些化合物是坦克酶-1和坦克酶-2抑制剂，并可用于治疗多种疾病，包括癌症。

  公开号：

  WO2014087165A1
• 作为产物：
  描述：

  2-氯-3-氰基吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四磷十氧化物 、 四丁基溴化铵 、 溶剂黄146 、 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 144.5h， 生成 3-cyano-2-phenylethynylpyridine
  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

文献信息

• Spin Frustrated Double Chain {[Fe(PZDA)H₂O)₂]·2H₂O}_n(H₂PZDA=2,3-Pyrazinedicarboxylic Acid)
  作者：Song Gao、Bao-Qing Ma、Tao Yi、Zhe-Ming Wang、Chun-Sheng Liao、Chun-Hua Yan、Guang-Xian Xu

  DOI：10.1246/cl.1999.773

  日期：1999.8

  A novel compound [Fe(PZDA)(H2O)2]·2H2O}n has been synthesized and its structure determined by X-ray diffraction analysis, which consists of a quasi-ladder-like double chain running along a axis where Fe(II) ions are linked through the carboxylic groups acting as the edges of the ladder and pyrazine rings functioning as the rungs. Variable-temperature magnetic susceptibility study indicates the presence of spin frustration in the double chain compound.

  合成了一种新化合物 [Fe(PZDA)(H2O)2]·2H2O}n，并通过 X 射线衍射分析确定了其结构。该化合物由沿 a 轴的准梯形双链构成，其中 Fe(II) 离子通过羧基相连，羧基作为梯子的边缘，而吡嗪环则作为梯子的横档。变温磁 susceptibili 研究表明，该双链化合物存在自旋挫折现象。
• A Facile Synthesis of 1,6-Naphthyridin-5(6<i>H</i>)-ones
  作者：Nagatoshi Nishiwaki、Mitsuo Komatsu、Yoshiki Ohshiro

  DOI：10.1055/s-1991-26375

  日期：——

  3-Cyano-2-(phenylethynyl)pyridine (1) was cyclized intramolecularly under acidic conditions to give 1,6-naphthyridin-5(6H)-one (2) and 5H-pyrano[4,3-b]pyridin-5-one (4). Pyranopyridine 4 was readily transformed to 2 or naphthyridinone 9 having an alkyl substituent at 6-position.

  3-氰基-2-(苯乙炔基)吡啶(1)在酸性条件下发生分子内环化反应，生成1,6-萘啶-5(6H)-酮(2)和5H-吡喃并[4,3-b]吡啶-5-酮(4)。吡喃并吡啶4很容易转化为2或萘啶酮9，后者在6位有一个烷基取代基。
• 一种钯催化制备苯基-2-（2’-氰基苯基）乙炔类化合物的方法
  申请人：浙江农林大学暨阳学院

  公开号：CN111704558B

  公开（公告）日：2023-05-30

  本发明公开了一种钯催化制备式(Ⅳ)所示的苯基‑2‑(2’‑氰基苯基)乙炔类化合物的方法，制备方法为：式(Ⅰ)所示的苯甲腈类化合物、式(Ⅱ)所示的乙炔和式(Ⅲ)所示的碘代苯类化合物，以氯化钯为催化剂，以碳酸钠为碱，以二甲基亚砜为溶剂，在氧气下充分反应反，所述的反应产物通过后处理制得苯基‑2‑(2’‑氰基苯基)乙炔类化合物。本发明方法化剂高效，符合绿色环保要求；催化体系适应性广，适用于大规模医药化工中间体生产。
• A unified approach to benzo[<i>c</i>]phenanthridines <i>via</i> the cascade dual-annulation/formylation of 2-alkynyl/alkenylbenzonitriles
  作者：Shalini Verma、Manoj Kumar、Akhilesh K. Verma

  DOI：10.1039/d3cc00197k

  日期：——

  A base-mediated versatile cascade dual-annulation and formylation of 2-alkenyl/alkynylbenzonitriles with 2-methylbenzonitriles has been established for the construction of four different classes of amino and amido substituted benzo[c]phenanthridines and benzo[c]phenanthrolines. The synthesized molecules could be of utmost relevance in pharmaceuticals. The transformation uses the solvent DMF as the

  已经建立了碱基介导的多功能级联双环化和 2-烯基/炔基苯甲腈与 2-甲基苯甲腈的甲酰化，用于构建四种不同类别的氨基和酰氨基取代的苯并 [c] 菲啶和苯并 [c]菲咯啉。合成的分子可能在药物中具有最大的相关性。该转化使用溶剂 DMF 作为甲酰源，用于合成酰胺基取代的支架。这种无过渡金属的独特策略能够在室温下在一个锅中形成多个 C-C 和 C-N 键。
• Sakamoto, Takao; An-Naka, Masayuki; Kondo, Yoshinori, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 5, p. 1890 - 1894
  作者：Sakamoto, Takao、An-Naka, Masayuki、Kondo, Yoshinori、Araki, Tomio、Yamanaka, Hiroshi

  DOI：——

  日期：——