4-cyano-3-phenoxypyridine | 78790-74-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-cyano-3-phenoxypyridine
• 英文别名: 3-Phenoxypyridine-4-carbonitrile
• CAS: 78790-74-6
• 化学式: C₁₂H₈N₂O
• 分子量: 196.208
• InChiKey: BLBNWYFNLQKNLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 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：
  45.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-cyano-3-phenoxypyridine 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 3-phenoxyisonicotinonitrile hydrochloride
  参考文献：
  名称：

  Chemoselective reactions of 3-chloroisonicotinonitrile

  摘要：

  DOI：

  10.1021/jo00334a014
• 作为产物：
  描述：

  4-<(hydroxyimino)methyl>-3-phenoxypyridine 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以67%的产率得到4-cyano-3-phenoxypyridine
  参考文献：
  名称：

  3-Phenoxypyridine 1-oxides as anticonvulsant agents

  摘要：

  The anticonvulsant activity of a series of 3-phenoxypyridine 1-oxides is described. An investigation carried out to optimize the activity/side effect ratio provided 4-methyl-3-phenoxypyridine 1-oxide, 3, as the derivative of choice. Overall, 3 has a pharmacological profile that is very similar to phenytoin. It exhibited significant anticonvulsant activity at doses that did not produce ataxia or sedation but caused increased spontaneous behavioral activity not seen with most anticonvulsants. The short duration of pharmacological effect of 3 was attributed to metabolic hydroxylation at the C-4 pyridine methyl group; however, structural modifications designed to inhibit this metabolic pathway were unsuccessful.

  DOI：

  10.1021/jm00399a027

文献信息

• Synthesis and Conformational Dynamics of the Reported Structure of Xylopyridine A
  作者：Robert-André F. Rarig、Mai N. Tran、David M. Chenoweth

  DOI：10.1021/ja404737q

  日期：2013.6.19

  Natural products have served as a rich source for the discovery of new nucleic acid targeting molecules for more than half a century. However, our ability to design molecules that bind nucleic acid motifs in a sequence- and/or structure-selective manner is still in its infancy. Xylopyridine A, a naturally occurring molecule of unprecedented architecture, has been found to bind DNA by a unique mode of intercalation. Here we show that the structure proposed for xylopyridine A is not consistent with the characterization in the original isolation report and does not bind B-form DNA. Instead, we report that the originally proposed structure for xylopyridine A represents a new class of conformationally dynamic structure-selective quadruplex nucleic acid binder. The unique molecular conformation locks out nonspecific intercalative binding modes and provides a starting point for the design of a new class of structure-specific nucleic acid binder.
• LAMATTINA, J. L.;TAYLOR, R. L., J. ORG. CHEM., 1981, 46, N 21, 4179-4182
  作者：LAMATTINA, J. L.、TAYLOR, R. L.

  DOI：——

  日期：——
• PAVIA, MICHAEL R.;TAYLOR, CHARLES P.;HERSHENSON, FRED M.;LOBBESTAEL, SAND+, J. MED. CHEM., 31,(1988) N 4, 841-847
  作者：PAVIA, MICHAEL R.、TAYLOR, CHARLES P.、HERSHENSON, FRED M.、LOBBESTAEL, SAND+

  DOI：——

  日期：——
• Chemoselective reactions of 3-chloroisonicotinonitrile
  作者：John L. LaMattina、Richard L. Taylor

  DOI：10.1021/jo00334a014

  日期：1981.10
• 3-Phenoxypyridine 1-oxides as anticonvulsant agents
  作者：Michael R. Pavia、Charles P. Taylor、Fred M. Hershenson、Sandra J. Lobbestael、Donald E. Butler

  DOI：10.1021/jm00399a027

  日期：1988.4

  The anticonvulsant activity of a series of 3-phenoxypyridine 1-oxides is described. An investigation carried out to optimize the activity/side effect ratio provided 4-methyl-3-phenoxypyridine 1-oxide, 3, as the derivative of choice. Overall, 3 has a pharmacological profile that is very similar to phenytoin. It exhibited significant anticonvulsant activity at doses that did not produce ataxia or sedation but caused increased spontaneous behavioral activity not seen with most anticonvulsants. The short duration of pharmacological effect of 3 was attributed to metabolic hydroxylation at the C-4 pyridine methyl group; however, structural modifications designed to inhibit this metabolic pathway were unsuccessful.