3-(2-cyano-4-nitrophenoxy)pyridine | 849044-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-cyano-4-nitrophenoxy)pyridine
• 英文别名: 5-Nitro-2-pyridin-3-yloxybenzonitrile
• CAS: 849044-12-8
• 化学式: C₁₂H₇N₃O₃
• mdl: MFCD08497007
• 分子量: 241.206
• InChiKey: WXCBXJCTUPDQLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 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：
  91.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-羟基吡啶 、 2-氯-5-硝基苯甲腈 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 3-(2-cyano-4-nitrophenoxy)pyridine
  参考文献：
  名称：

  Anti-enteroviral activity of new MDL-860 analogues: Synthesis, in vitro/in vivo studies and QSAR analysis

  摘要：

  A series of 60 nitrobenzonitrile analogues of the anti-viral agent MDL-860 were synthesized (50 of which are new) and evaluated for their activity against three types of enteroviruses (coxsackievirus B1, coxsackievirus B3 and poliovirus 1). Among them, six diaryl ethers (20e, 27e, 28e, 29e, 33e and 35e) demonstrated high in vitro activity (SI > 50) towards at least one of the tested viruses and very low cytotoxicity against human cells. Compound 27e possesses the broadest spectrum of activity towards all tested viruses in the same way as MDL-860 does. The most active derivatives (27e, 29e and 35e) against coxsackievirus B1 were tested in vivo in newborn mice experimentally infected with 20 MLD50, of coxsackievirus B1. Compound 29e showed promising in vivo activity (protection index 26% and 4 days lengthening of mean survival time). QSAR analysis of the sub-stituent effects on the in vitro cytotoxicity (CC50) and anti-viral activity of the nitrobenzonitrile derivatives was carried out and adequate QSAR models for the anti-viral activity of the compounds against poliovirus 1 and coxsackievirus B1 were constructed.

  DOI：

  10.1016/j.bioorg.2019.02.020

文献信息

• [EN] QUINAZOLINE DERIVATIVES AS ERBB RECEPTOR TYROSINE KINASES<br/>[FR] DERIVES DE QUINAZOLINE UTILISES COMME TYROSINE KINASES DU RECEPTEUR ERBB
  申请人：ASTRAZENECA AB

  公开号：WO2005118572A1

  公开（公告）日：2005-12-15

  The invention concerns quinazoline derivatives of the formula (I), wherein each of R1, R2, R3, R4, R5, R6, R7, X1, Q1, m and n have any of the meanings defined in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an antiproliferative agent in the prevention or treatment of tumours which are sensitive to inhibition of erbB receptor tyrosine kinases.

  该发明涉及公式(I)的喹唑啉衍生物，其中R1、R2、R3、R4、R5、R6、R7、X1、Q1、m和n中的每个都具有描述中定义的任意含义；它们的制备方法，含有它们的药物组合物以及它们在制造用作抗增殖剂的药物中的用途，用于预防或治疗对erbB受体酪氨酸激酶抑制敏感的肿瘤。
• Quinazoline Derivatives as Erbb Receptor Tyrosine kinases
  申请人：Bradbury Hugh Robert

  公开号：US20070232607A1

  公开（公告）日：2007-10-04

  The invention concerns quinazoline derivatives of the formula (I), wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X 1 , Q 1 , m and n have any of the meanings defined in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an antiproliferative agent in the prevention or treatment of tumours which are sensitive to inhibition of erbB receptor tyrosine kinases.

  这项发明涉及公式（I）的喹唑啉衍生物，其中R1、R2、R3、R4、R5、R6、R7、X1、Q1、m和n中的每一个都具有描述中定义的任何含义；它们的制备过程，含有它们的制药组合物以及它们在制造用作抗增殖剂的药物的过程中的使用，用于预防或治疗对erbB受体酪氨酸激酶抑制敏感的肿瘤。
• QUINAZOLINE DERIVATIVES AS ERBB RECEPTOR TYROSINE KINASES
  申请人：AstraZeneca AB

  公开号：EP1756088A1

  公开（公告）日：2007-02-28
• Anti-enteroviral activity of new MDL-860 analogues: Synthesis, in vitro/in vivo studies and QSAR analysis
  作者：Ivanka Nikolova、Ivaylo Slavchev、Martin Ravutsov、Miroslav Dangalov、Yana Nikolova、Irena Zagranyarska、Adelina Stoyanova、Nadya Nikolova、Lucia Mukova、Petar Grozdanov、Rosica Nikolova、Boris Shivachev、Victor E. Kuz'min、Liudmila N. Ognichenko、Angel S. Galabov、Georgi M. Dobrikov

  DOI：10.1016/j.bioorg.2019.02.020

  日期：2019.4

  A series of 60 nitrobenzonitrile analogues of the anti-viral agent MDL-860 were synthesized (50 of which are new) and evaluated for their activity against three types of enteroviruses (coxsackievirus B1, coxsackievirus B3 and poliovirus 1). Among them, six diaryl ethers (20e, 27e, 28e, 29e, 33e and 35e) demonstrated high in vitro activity (SI > 50) towards at least one of the tested viruses and very low cytotoxicity against human cells. Compound 27e possesses the broadest spectrum of activity towards all tested viruses in the same way as MDL-860 does. The most active derivatives (27e, 29e and 35e) against coxsackievirus B1 were tested in vivo in newborn mice experimentally infected with 20 MLD50, of coxsackievirus B1. Compound 29e showed promising in vivo activity (protection index 26% and 4 days lengthening of mean survival time). QSAR analysis of the sub-stituent effects on the in vitro cytotoxicity (CC50) and anti-viral activity of the nitrobenzonitrile derivatives was carried out and adequate QSAR models for the anti-viral activity of the compounds against poliovirus 1 and coxsackievirus B1 were constructed.