2-(乙基氨基)-4-吡啶甲腈 | 87121-58-2

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 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
• 中文名称: 2-(乙基氨基)-4-吡啶甲腈
• 英文名称: 2-(ethylamino)isonicotinonitrile
• 英文别名: 2-(ethylamino)pyridine-4-carbonitrile
• CAS: 87121-58-2
• 化学式: C₈H₉N₃
• 分子量: 147.18
• InChiKey: QJJCFTFAVGJRPR-UHFFFAOYSA-N

物化性质

• 沸点：
  276℃
• 密度：
  1.10
• 闪点：
  121℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  48.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(乙基氨基)-4-吡啶甲腈 在 氨 、 氢气 、 镍 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、333.4 kPa 条件下， 反应 3.0h， 以79%的产率得到4-(aminomethyl)-N-ethylpyridin-2-amine
  参考文献：
  名称：

  Discovery of an N-(2-aminopyridin-4-ylmethyl)nicotinamide derivative: a potent and orally bioavailable NCX inhibitor

  摘要：

  Ca2+ overload in myocardial cells is responsible for arrhythmia. Sodium-calcium exchanger (NCX) inhibitors are more effective than sodium hydrogen exchanger (NHE) inhibitors with regard to modulation of Ca2+ overload, because NCX inhibitors can directly inhibit the influx of Ca2+ into cells. NCX is an attractive target for the treatment of heart failure and ischemia-reper-fusion. We have designed and synthesized a series of N-(2-aminopyridin-4-ylmethyl)nicotinamide derivatives, based on compound 5. We have discovered a novel NCX inhibitor (23h) with an IC50 value of 0.12 mu M against reverse NCX. The inhibitory activities of our NCX inhibitors against cytochrome P450 were also evaluated. The effects on heart failure and the pharmacokinetic profile of compound 23h are discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.052
• 作为产物：
  描述：

  2-氯-4-氰基吡啶 、 乙胺 以 四氢呋喃 为溶剂， 反应 3.0h， 以49%的产率得到2-(乙基氨基)-4-吡啶甲腈
  参考文献：
  名称：

  Discovery of an N-(2-aminopyridin-4-ylmethyl)nicotinamide derivative: a potent and orally bioavailable NCX inhibitor

  摘要：

  Ca2+ overload in myocardial cells is responsible for arrhythmia. Sodium-calcium exchanger (NCX) inhibitors are more effective than sodium hydrogen exchanger (NHE) inhibitors with regard to modulation of Ca2+ overload, because NCX inhibitors can directly inhibit the influx of Ca2+ into cells. NCX is an attractive target for the treatment of heart failure and ischemia-reper-fusion. We have designed and synthesized a series of N-(2-aminopyridin-4-ylmethyl)nicotinamide derivatives, based on compound 5. We have discovered a novel NCX inhibitor (23h) with an IC50 value of 0.12 mu M against reverse NCX. The inhibitory activities of our NCX inhibitors against cytochrome P450 were also evaluated. The effects on heart failure and the pharmacokinetic profile of compound 23h are discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.052

文献信息

• Diarylthiazole: An Antimycobacterial Scaffold Potentially Targeting PrrB-PrrA Two-Component System
  作者：Eknath Bellale、Maruti Naik、Varun VB、Anisha Ambady、Ashwini Narayan、Sudha Ravishankar、Vasanthi Ramachandran、Parvinder Kaur、Robert McLaughlin、James Whiteaker、Sapna Morayya、Supreeth Guptha、Sreevalli Sharma、Anandkumar Raichurkar、Disha Awasthy、Vijayshree Achar、Prakash Vachaspati、Balachandra Bandodkar、Manoranjan Panda、Monalisa Chatterji

  DOI：10.1021/jm500833f

  日期：2014.8.14

  Diarylthiazole (DAT), a hit from diversity screening, was found to have potent antimycobacterial activity against Mycobacterium tuberculosis (Mtb). In a systematic medicinal chemistry exploration, we demonstrated chemical opportunities to optimize the potency and physicochemical properties. The effort led to more than 10 compounds with submicromolar MICs and desirable physicochemical properties. The potent antimycobacterial activity, in conjunction with low molecular weight, made the series an attractive lead (antibacterial ligand efficiency (ALE)>0.4). The series exhibited excellent bactericidal activity and was active against drug-sensitive and resistant Mtb. Mutational analysis showed that mutations in prrB impart resistance to DAT compounds but not to reference drugs tested. The sensor kinase PrrB belongs to the PrrBA two component system and is potentially the target for DAT. PrrBA is a conserved, essential regulatory mechanism in Mtb and has been shown to have a role in virulence and metabolic adaptation to stress. Hence, DATs provide an opportunity to understand a completely new target system for antimycobacterial drug discovery.
• LaMattina, Journal of Heterocyclic Chemistry, 1983, vol. 20, # 3, p. 533 - 538
  作者：LaMattina

  DOI：——

  日期：——
• LAMATTINA, J. L., J. HETEROCYCL. CHEM., 1983, 20, N 3, 533-538
  作者：LAMATTINA, J. L.

  DOI：——

  日期：——
• NOVEL FXR (NR1H4) MODULATING COMPOUNDS
  申请人：Gilead Sciences, Inc.

  公开号：EP3233831B1

  公开（公告）日：2019-02-20
• 3-AMINO-1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONES
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：US20170101391A1

  公开（公告）日：2017-04-13

  Compounds of formula (I) which are inhibitors of Bub1 kinase, processes for their production and their use as pharmaceuticals.