1-[2-(二甲基氨基)-5-嘧啶基]乙酮 | 265107-46-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-[2-(二甲基氨基)-5-嘧啶基]乙酮
• 英文名称: 1-(2-dimethylaminopyrimidin-5-yl)ethanone
• 英文别名: 1-(2-(Dimethylamino)pyrimidin-5-yl)ethanone；1-[2-(dimethylamino)pyrimidin-5-yl]ethanone
• CAS: 265107-46-8
• 化学式: C₈H₁₁N₃O
• 分子量: 165.195
• InChiKey: GRJYPJAIITXYGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-(二甲基氨基)-5-嘧啶基]乙酮 在 乙酸铵 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 5-(3-Bromo-phenyl)-7-(2-dimethylamino-pyrimidin-5-yl)-pyrido[2,3-d]pyrimidin-4-ylamine
  参考文献：
  名称：

  5-(3-Bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine: structure–activity relationships of 7-substituted heteroaryl analogs as non-nucleoside adenosine kinase inhibitors

  摘要：

  4-Amino-5,7-disubstituted pyridopyrimidines are potent, non-nucleoside inhibitors of adenosine kinase (AK). We recently identified a potent, orally efficacious analog, 4 containing a 7-pyridylmorpholine substituted ring system as the key structural element of this template. In this report, we disclose the pharmacologic effects of five- and six-membered heterocyclic ring replacements for the pyridine ring in 4. These replacements were found to have interesting effects on in vivo efficacy and genotoxicity as well as in vitro potency. We discovered that the nitrogen in the heterocyclic ring at C(7) is important for the modulation of mutagenic side effects (Ames assay). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.023
• 作为产物：
  描述：

  5-溴-2-(二甲基氨基)嘧啶 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 2.0h， 生成 1-[2-(二甲基氨基)-5-嘧啶基]乙酮
  参考文献：
  名称：

  5-(3-Bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine: structure–activity relationships of 7-substituted heteroaryl analogs as non-nucleoside adenosine kinase inhibitors

  摘要：

  4-Amino-5,7-disubstituted pyridopyrimidines are potent, non-nucleoside inhibitors of adenosine kinase (AK). We recently identified a potent, orally efficacious analog, 4 containing a 7-pyridylmorpholine substituted ring system as the key structural element of this template. In this report, we disclose the pharmacologic effects of five- and six-membered heterocyclic ring replacements for the pyridine ring in 4. These replacements were found to have interesting effects on in vivo efficacy and genotoxicity as well as in vitro potency. We discovered that the nitrogen in the heterocyclic ring at C(7) is important for the modulation of mutagenic side effects (Ames assay). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.023

文献信息

• [EN] NOVEL COMPOUNDS FOR THE DIAGNOSIS, TREATMENT AND PREVENTION OF DISEASES ASSOCIATED WITH THE AGGREGATION OF ALPHA-SYNUCLEIN<br/>[FR] NOUVEAUX COMPOSÉS POUR LE DIAGNOSTIC, LE TRAITEMENT ET LA PRÉVENTION DE MALADIES ASSOCIÉES À L'AGRÉGATION DE L'ALPHA-SYNUCLÉINE
  申请人：MODAG GMBH

  公开号：WO2021099518A1

  公开（公告）日：2021-05-27

  The present invention relates to compounds represented by general formula (la), (lb), (lla) or(llb). These compounds are suitable for imaging alpha-synuclein and for diagnosing diseases which are associated with the aggregation of alpha-synuclein. The compounds are also useful for treating and preventing diseases which are associated with the aggregation of alpha-synuclein.

  本发明涉及由通式(la)、(lb)、(lla)或(llb)表示的化合物。这些化合物适用于成像α-突触核蛋白和诊断与α-突触核蛋白聚集相关的疾病。这些化合物还适用于治疗和预防与α-突触核蛋白聚集相关的疾病。
• Acetylation of <i>N</i>-Heteroaryl Bromides via PdCl₂/(<i>o</i>-tolyl)₃P Catalyzed Heck Reactions
  作者：Xiaochun Tao、Lisheng Cai、Tianxiong He、Xinyan Wu、Victor Pike

  DOI：10.1055/s-2008-1032193

  日期：2008.3

  user-friendly and convenient method for the acetylation of N-heteroaryl bromides is described. This process is based on the palladium-catalyzed olefination of an N-heteroaryl bromide with butyl vinyl ether, followed by acid hydrolysis of the intermediate heteroaryl vinyl ether in situ. Isopropanol at 85 °C, in the presence of K 3 PO 4 ·3H 2 O (2 equiv), PdCl 2 (2 mol%) and ( O-tolyl) 3 P (4 mol%), provided

  描述了一种新的用户友好和方便的 N-杂芳基溴乙酰化方法。该方法基于钯催化的 N-杂芳基溴化物与丁基乙烯基醚的烯化反应，然后是中间体杂芳基乙烯基醚的原位酸水解。异丙醇在 85 °C，在 K 3 PO 4 ·3H 2 O (2 equiv)、PdCl 2 (2 mol%) 和 ( O-tolyl) 3 P (4 mol%) 存在下，提供了最佳条件，给出N-杂芳基溴的产率高达 75%。
• 5-(3-Bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine: structure–activity relationships of 7-substituted heteroaryl analogs as non-nucleoside adenosine kinase inhibitors
  作者：Mark A. Matulenko、Chih-Hung Lee、Meiqun Jiang、Robin R. Frey、Marlon D. Cowart、Erol K. Bayburt、Stanley DiDomenico、Gregory A. Gfesser、Arthur Gomtsyan、Guo Zhu Zheng、Jeffery A. McKie、Andrew O. Stewart、Haixia Yu、Kathy L. Kohlhaas、Karen M. Alexander、Steve McGaraughty、Carol T. Wismer、Joseph Mikusa、Kennan C. Marsh、Ronald D. Snyder、Marilyn S. Diehl、Elizabeth A. Kowaluk、Michael F. Jarvis、Shripad S. Bhagwat

  DOI：10.1016/j.bmc.2005.03.023

  日期：2005.6

  4-Amino-5,7-disubstituted pyridopyrimidines are potent, non-nucleoside inhibitors of adenosine kinase (AK). We recently identified a potent, orally efficacious analog, 4 containing a 7-pyridylmorpholine substituted ring system as the key structural element of this template. In this report, we disclose the pharmacologic effects of five- and six-membered heterocyclic ring replacements for the pyridine ring in 4. These replacements were found to have interesting effects on in vivo efficacy and genotoxicity as well as in vitro potency. We discovered that the nitrogen in the heterocyclic ring at C(7) is important for the modulation of mutagenic side effects (Ames assay). (c) 2005 Elsevier Ltd. All rights reserved.