N,N-dimethyl-N'-(3-methylpyridyl)formamidine | 36172-55-1

• 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
• 英文名称: N,N-dimethyl-N'-(3-methylpyridyl)formamidine
• 英文别名: N,N-dimethyl-N'-(3-methylpyridin-2-yl)formimideamide；N,N-dimethyl-N′-(3-methylpyridin-2-yl)formimidamide；N,N-Dimethyl-N'-(3-methylpyridyl-2)formamidin；N,N-dimethyl-N'-(3-methyl-pyridin-2-yl)-formamidine；(E)-N,N-Dimethyl-N'-(3-methylpyridin-2-yl)formimidamide；N,N-dimethyl-N'-(3-methylpyridin-2-yl)methanimidamide
• CAS: 36172-55-1
• 化学式: C₉H₁₃N₃
• 分子量: 163.222
• InChiKey: SBPJSTICBJFIJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-N'-(3-methylpyridyl)formamidine 在 正丁基锂 、 盐酸羟胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 7.0h， 生成 5-iodo-8-methyl-[1,2,4]triazolo[1,5-a]pyridine
  参考文献：
  名称：

  1,2,4-Triazolo-[1,5-a]pyridine HIF Prolylhydroxylase Domain-1 (PHD-1) Inhibitors With a Novel Monodentate Binding Interaction

  摘要：

  Herein we describe the identification of 4-{[1,2,4]triazolo[1,5-a]pyridin-5-yl}benzonitrile-based inhibitors of the hypoxia-inducible factor prolylhydroxylase domain-1 (PHD-1) enzyme. These inhibitors were shown to possess a novel binding mode by X-ray crystallography, in which the triazolo N1 atom coordinates in a hitherto unreported monodentate interaction with the active site Fe2+ ion, while the benzonitrile group accepts a hydrogen -bonding interaction from the side chain residue of Asn315. Further optimization led to potent PHD-1 inhibitors with good physicochemical and pharmacokinetic properties.

  DOI：

  10.1021/acs.jmedchem.7b00352
• 作为产物：
  描述：

  2-氨基-3-甲基吡啶 、 N,N-二甲基甲酰胺二甲基缩醛 以 甲苯 为溶剂， 反应 12.0h， 生成 N,N-dimethyl-N'-(3-methylpyridyl)formamidine
  参考文献：
  名称：

  1,2,4-Triazolo-[1,5-a]pyridine HIF Prolylhydroxylase Domain-1 (PHD-1) Inhibitors With a Novel Monodentate Binding Interaction

  摘要：

  Herein we describe the identification of 4-{[1,2,4]triazolo[1,5-a]pyridin-5-yl}benzonitrile-based inhibitors of the hypoxia-inducible factor prolylhydroxylase domain-1 (PHD-1) enzyme. These inhibitors were shown to possess a novel binding mode by X-ray crystallography, in which the triazolo N1 atom coordinates in a hitherto unreported monodentate interaction with the active site Fe2+ ion, while the benzonitrile group accepts a hydrogen -bonding interaction from the side chain residue of Asn315. Further optimization led to potent PHD-1 inhibitors with good physicochemical and pharmacokinetic properties.

  DOI：

  10.1021/acs.jmedchem.7b00352

文献信息

• Investigations on substituted (2-aminothiazol-5-yl)(imidazo[1,2-a]pyridin-3-yl)methanones for the treatment of Alzheimer’s disease
  作者：Sneha R. Sagar、Devendra Pratap Singh、Rajesh D. Das、Nirupa B. Panchal、Vasudevan Sudarsanam、Manish Nivsarkar、Kamala K. Vasu

  DOI：10.1016/j.bmc.2021.116091

  日期：2021.4
• Georgescu, Florentina; Georgescu, Emilian; Drǎghici, Constantin, Revue Roumaine de Chimie, 2005, vol. 50, # 5, p. 349 - 352
  作者：Georgescu, Florentina、Georgescu, Emilian、Drǎghici, Constantin、Iuhas, Paula C.、Filip, Petru I.

  DOI：——

  日期：——
• Synthesis of (aryloxy)alkylamines. 2. Novel imidazo-fused heterocycles with calcium channel blocking and local anesthetic activity
  作者：Pauline J. Sanfilippo、Maud Urbanski、Jeffery B. Press、Barry Dubinsky、John B. Moore

  DOI：10.1021/jm00119a026

  日期：1988.11

  A series of imidazo-fused heterocycles substituted with an aryloxy)alkylamine side chain were prepared as modifications to butoprozine (I) and found to possess calcium channel blocking activity similar in potency to that of bepridil in trachea smooth muscle and similar to that of verapamil in nitrendipine binding affinity in rabbit cardiac muscle. Of the various imidazo-fused heterocycles prepared, the imidazo[1,2-a]pyridines were also found to be potent local anesthetic agents. While most compounds in this series were equipotent to lidocaine in our initial screen, compounds 2 and 35 showed local anesthetic activity approximately 100 times more potent than lidocaine in our preliminary assays. These compounds represent a novel structural class of local anesthetic agents, and compound 2 is under further investigation.
• New syntheses of s-triazolo[1,5-a]pyridines and s-triazolo[5,1-a]isoquinoline
  作者：Yang-I Lin、S. A. Lang

  DOI：10.1021/jo00328a028

  日期：1981.7