1,2-dihydro-2-oxo-6-(3-pyridyl)-3-pyridinecarbonitrile | 39883-43-7

• 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: 1,2-dihydro-2-oxo-6-(3-pyridyl)-3-pyridinecarbonitrile
• 英文别名: 6-oxo-1,6-dihydro-[2,3']bipyridinyl-5-carbonitrile；6-(3-Pyridyl)-1,2-dihydro-2-oxonicotinonitrile；2-oxo-6-pyridin-3-yl-1H-pyridine-3-carbonitrile
• CAS: 39883-43-7
• 化学式: C₁₁H₇N₃O
• 分子量: 197.196
• InChiKey: ZLDBKVWPDQMGCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-dihydro-2-oxo-6-(3-pyridyl)-3-pyridinecarbonitrile 在 二苯基磷酸 、 氢溴酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 生成 benzyl N-(2-oxo-6-pyridin-3-yl-1H-pyridin-3-yl)carbamate
  参考文献：
  名称：

  Nonpeptidic Inhibitors of Human Leukocyte Elastase. 2. Design, Synthesis, and in vitro Activity of a Series of 3-Amino-6-aryl-2-oxopyridyl Trifluoromethyl Ketones

  摘要：

  A series of potent nonpeptidic inhibitors of the enzyme human leukocyte elastase (HLE) is reported. These inhibitors contain a 3-amino-2-pyridone ring as a central template in which the pyridone carbonyl and 3-position NH group are thought to form important hydrogen bonding interactions with the Val-216 residue of HLE. Substitution of the 6-position of the pyridone ring by various alkyl and aryl groups was found to afford increases in the in vitro potency of these inhibitors. A 6-position phenyl group, compound 10f, was found to result in a large increase in binding affinity, which was not obtained when the phenyl group was placed in either the 4- or 5-position of the molecule. Compound 10f was found to have good selectivity for HLE over other proteolytic enzymes, with the exception of bovine pancreatic chymotrypsin (BPC). Substitution of the 6-phenyl group in these molecules was found to decrease binding affinity for BPC without adversely affecting affinity for HLE.

  DOI：

  10.1021/jm00046a015
• 作为产物：
  描述：

  5-cyano-1,6-dihydro-6-oxo-2-(3-pyridyl)-3-pyridinecarboxylic acid 在 铜 作用下， 以 喹啉 为溶剂， 反应 5.0h， 以41%的产率得到1,2-dihydro-2-oxo-6-(3-pyridyl)-3-pyridinecarbonitrile
  参考文献：
  名称：

  Mosti; Schenone; Del Mar Mahiques, Il Farmaco, 1994, vol. 49, # 9, p. 559 - 566

  摘要：

  DOI：

文献信息

• Substituted pyridinones
  申请人：Devadas Balekudru

  公开号：US20050176775A1

  公开（公告）日：2005-08-11

  Disclosed are compounds of Formula I and pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 , R 4 , and R 5 are defined herein. These compounds are useful for treating diseases and conditions caused or exacerbated by unregulated p38 MAP Kinase and/or TNF activity. Pharmaceutical compositions containing the compounds, methods of preparing the compounds and methods of treatment using the compounds are also disclosed.

  本发明涉及式I的化合物及其药学上可接受的盐，其中R1、R2、R3、R4和R5在此被定义。这些化合物可用于治疗由未调节的p38 MAP激酶和/或TNF活性引起或加剧的疾病和状况。本发明还涉及含有这些化合物的药物组合物、制备这些化合物的方法以及使用这些化合物的治疗方法。
• Synthesis of some new bipyridines, thieno[2,3-b]pyridines, and pyrazolo[3,4-b]pyridines
  作者：Mahmoud A. Mohamed

  DOI：10.1002/jhet.802

  日期：2012.1

  3‐hydroxy‐1‐(pyridin‐3‐yl)prop‐2‐en‐1‐one gave 6‐oxo‐[2,3′]bipyridine 5a and 6‐thioxo‐[2,3′]bipyridine 5b derivatives, respectively. Compound 5b upon treatment with different methylenes 8 gave thieno[2,3‐b]pyridines 10. Treatment of 5b with iodomethane gave bipyridine derivative 7, which cyclocondensed with hydrazines 11 to give pyrazolo[3,4‐b]pyridines 13. J. Heterocyclic Chem., (2012).

  氰基乙酰胺和氰基硫代乙酰胺与3-羟基-1-（吡啶-3-基）丙-2-烯-1-酮的钠盐进行环缩合得到6-氧代[2,3']联吡啶5a和6-硫代[[ 2,3']联吡啶5b衍生物。用不同的亚甲基8处理后的化合物5b得到噻吩并[2,3- b ]吡啶10。用碘甲烷处理5b得到联吡啶衍生物7，联吡啶衍生物7与肼11环缩合，得到吡唑并[3,4- b ]吡啶13。J.杂环化​​学。（2012）。
• Mosti Luisa, Schenone Pietro, Del Mar Mahiques Maria, Dorigo Paola, Fracc+, Farmaco, 49 (1994) N 9, S 559-566
  作者：Mosti Luisa, Schenone Pietro, Del Mar Mahiques Maria, Dorigo Paola, Fracc+

  DOI：——

  日期：——
• US3948903A
  申请人：——

  公开号：US3948903A

  公开（公告）日：1976-04-06
• US7067540B2
  申请人：——

  公开号：US7067540B2

  公开（公告）日：2006-06-27