N-<4(5)-β-Naphthyl-1H-imidazol-2-yl>acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-<4(5)-β-Naphthyl-1H-imidazol-2-yl>acetamide
• 英文别名: N-(5-naphthalen-2-yl-1H-imidazol-2-yl)acetamide
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: AEWGPOCEYYUJJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-<4(5)-β-Naphthyl-1H-imidazol-2-yl>acetamide 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以83%的产率得到2-Amino-4(5)-β-naphthylimidazole sulfate
  参考文献：
  名称：

  A Simple and Practical Synthesis of 2-Aminoimidazoles

  摘要：

  A new and simple two-step procedure to synthesize 2-aminoimidazoles (2-AI's) from readily available materials has been developed. The cyclization reaction of alpha-halo ketones and N-acetylguanidine in acetonitrile (MeCN) at reflux, or in dimethylformamide (DMF) at ambient temperature, gives 4(5)-substituted and 4,5-disubstituted N-(1H-imidazol-2-yl)acetamides, which are then hydrolyzed to their respective 2-AI's. In general, the purified products were isolated in good yields. We have prepared several examples and have demonstrated the usefulness of this method by its application in the total synthesis of 8, an interesting histamine analog, and oroidin, 15, a marine natural product isolated from various sponges.

  DOI：

  10.1021/jo00103a021
• 作为产物：
  描述：

  2-溴代-2-乙酰基萘 、 N-乙酰基胍 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以58%的产率得到N-<4(5)-β-Naphthyl-1H-imidazol-2-yl>acetamide
  参考文献：
  名称：

  A Simple and Practical Synthesis of 2-Aminoimidazoles

  摘要：

  A new and simple two-step procedure to synthesize 2-aminoimidazoles (2-AI's) from readily available materials has been developed. The cyclization reaction of alpha-halo ketones and N-acetylguanidine in acetonitrile (MeCN) at reflux, or in dimethylformamide (DMF) at ambient temperature, gives 4(5)-substituted and 4,5-disubstituted N-(1H-imidazol-2-yl)acetamides, which are then hydrolyzed to their respective 2-AI's. In general, the purified products were isolated in good yields. We have prepared several examples and have demonstrated the usefulness of this method by its application in the total synthesis of 8, an interesting histamine analog, and oroidin, 15, a marine natural product isolated from various sponges.

  DOI：

  10.1021/jo00103a021

文献信息

• Carboxylic acid derivatives, medicaments comprising these compounds, their use and processes for their production
  申请人：Boehringer Ingelheim Pharma KG

  公开号：US20030055263A1

  公开（公告）日：2003-03-20

  The present application relates to the use of the carboxylic acid derivatives of general formula R 1 —A—B—R 2 (I) wherein R 1 , R 2 , A and B are defined as in claim 1 , the isomers and the salts thereof, particularly the physiologically acceptable salts thereof, which have an inhibitory effect on telomerase, processes for the preparation thereof, pharmaceutical compositions containing these compounds and the use thereof as well as the preparation thereof.

  本申请涉及一般公式R1—A—B—R2(I)的羧酸衍生物的使用，其中R1、R2、A和B的定义如权利要求1中所述，其异构体和盐，特别是其生理上可接受的盐，对端粒酶具有抑制作用，其制备方法，含有这些化合物的药物组合物以及其用途，以及其制备方法。
• [DE] CARBONSÄUREDERIVATE, DIESE VERBINDUNGEN ENTHALTENDE ARZNEIMITTEL, DEREN VERWENDUNG UND HERSTELLUNG<br/>[EN] CARBOXYLIC ACID DERIVATIVES, MEDICAMENTS CONTAINING THESE COMPOUNDS, THEIR USE AND THE PRODUCTION THEREOF<br/>[FR] DERIVES D'ACIDE CARBOXYLIQUE, MEDICAMENTS CONTENANT CES COMPOSES, LEUR UTILISATION ET LEUR PRODUCTION
  申请人：BOEHRINGER INGELHEIM PHARMA

  公开号：WO2003006443A2

  公开（公告）日：2003-01-23

  Die vorliegende Anmeldung betrifft die Verwendung der Carbonsäurederivate der allgemeinen Formel R1 - A - B - R2 (I), in der R1, R2, A und B wie im Anspruch 1 definiert sind, deren Isomere und deren Salze, insbesondere deren physiologisch verträglichen Salze, welche eine Hemmwirkung auf die Telomerase aufweisen, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung sowie deren Herstellung.
• A Simple and Practical Synthesis of 2-Aminoimidazoles
  作者：Thomas L. Little、Stephen E. Webber

  DOI：10.1021/jo00103a021

  日期：1994.12

  A new and simple two-step procedure to synthesize 2-aminoimidazoles (2-AI's) from readily available materials has been developed. The cyclization reaction of alpha-halo ketones and N-acetylguanidine in acetonitrile (MeCN) at reflux, or in dimethylformamide (DMF) at ambient temperature, gives 4(5)-substituted and 4,5-disubstituted N-(1H-imidazol-2-yl)acetamides, which are then hydrolyzed to their respective 2-AI's. In general, the purified products were isolated in good yields. We have prepared several examples and have demonstrated the usefulness of this method by its application in the total synthesis of 8, an interesting histamine analog, and oroidin, 15, a marine natural product isolated from various sponges.