N-<2-(acetylamino)ethyl>guanidine | 44956-50-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-<2-(acetylamino)ethyl>guanidine
• 英文别名: 2-Acetamino-ethylguanidin；N-(2-Guanidino-ethyl)-acetamid；N-[2-(diaminomethylideneamino)ethyl]acetamide
• CAS: 44956-50-5
• 化学式: C₅H₁₂N₄O
• 分子量: 144.176
• InChiKey: IJWTXMMAUQPBAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.5
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-3-phenylamino-acrylonitrile 、 N-<2-(acetylamino)ethyl>guanidine 在 sodium methylate 作用下， 以 乙醇 为溶剂， 生成 N-[2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]ethyl]acetamide
  参考文献：
  名称：

  Identification and SAR of novel diaminopyrimidines. Part 2: The discovery of RO-51, a potent and selective, dual P2X3/P2X2/3 antagonist for the treatment of pain

  摘要：

  The purinoceptor subtypes P2X(3) and P2X(2/3) have been shown to play a pivotal role in models of various pain conditions. Identification of a potent and selective dual P2X(3)/P2X(2/3) diaminopyrimidine antagonist RO-4 prompted subsequent optimization of the template. This paper describes the SAR and optimization of the diaminopyrimidine ring and particularly the substitution of the 2-amino group. The discovery of the highly potent and drug-like dual P2X(3)/P2X(2/3) antagonist RO-51 is presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.097
• 作为产物：
  描述：

  N-<2-(acetylamino)ethyl>-N'-tosylguanidine 在 氨 、 sodium 、 氯化铵 作用下， 生成 N-<2-(acetylamino)ethyl>guanidine
  参考文献：
  名称：

  Acylation of dibasic compounds containing amino amidine and aminoguanidine functions

  摘要：

  DOI：

  10.1021/jo00325a006

文献信息

• Syntheses of Aminoalkylguanidine Derivatives.
  作者：Tadakazu Tsuji、Hiroko Momona、Takeo Ueda

  DOI：10.1248/cpb.15.936

  日期：——

  The hydrochlorides of N1-benzyl-2-methyl-1, 2-propanediamine (I) and 5-amino-1, 3-dibenzyl-5-methylhexahydropyrimidine (II) were debenzylated by the catalytic hydrogenation under pressure. 2-Methyl-1, 2-propanediamine (III) which obtained from I, was derived to monoguanidine compound. The structure of this compound was concluded to be (2-amino-2-methylpropyl) guanidine from the comparison of the infrared spectra of related compounds. 2-Methyl-1, 2, 3-propanetriamine obtained from II, its starting material II, and other ethylenediamine derivatives were also guanidilated by the action of S-methylisothiourea sulfate.

  N1-苄基-2-甲基-1,2-丙二胺（I）和 5-氨基-1,3-二苄基-5-甲基六氢嘧啶（II）的盐酸盐在加压催化氢化作用下发生脱苄基反应。由 I 得到的 2-甲基-1, 2-丙二胺（III）被衍生成单胍化合物。通过比较相关化合物的红外光谱，可以断定该化合物的结构为（2-氨基-2-甲基丙基）胍。从 II 中得到的 2-甲基-1，2，3-丙三胺、其起始原料 II 和其他乙二胺衍生物也在硫酸 S-甲基异硫脲的作用下被胍化。
• Acylation of dibasic compounds containing amino amidine and aminoguanidine functions
  作者：Peter L. Barker、Paul L. Gendler、Henry Rapoport

  DOI：10.1021/jo00325a006

  日期：1981.6
• Identification and SAR of novel diaminopyrimidines. Part 2: The discovery of RO-51, a potent and selective, dual P2X3/P2X2/3 antagonist for the treatment of pain
  作者：Alam Jahangir、Muzaffar Alam、David S. Carter、Michael P. Dillon、Daisy Joe Du Bois、Anthony P.D.W. Ford、Joel R. Gever、Clara Lin、Paul J. Wagner、Yansheng Zhai、Jeff Zira

  DOI：10.1016/j.bmcl.2009.01.097

  日期：2009.3

  The purinoceptor subtypes P2X(3) and P2X(2/3) have been shown to play a pivotal role in models of various pain conditions. Identification of a potent and selective dual P2X(3)/P2X(2/3) diaminopyrimidine antagonist RO-4 prompted subsequent optimization of the template. This paper describes the SAR and optimization of the diaminopyrimidine ring and particularly the substitution of the 2-amino group. The discovery of the highly potent and drug-like dual P2X(3)/P2X(2/3) antagonist RO-51 is presented. (C) 2009 Elsevier Ltd. All rights reserved.