3-(4-氨基苯基)丙基氯 | 396124-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(4-氨基苯基)丙基氯
• 英文名称: 3-(4-aminophenyl)propyl chloride
• 英文别名: 4-(3-chloro-propyl)-aniline；4-Amino-1-(γ-chlor-propyl)-benzol；4-(γ-Chlor-propyl)-anilin；4-(3-Chlor-propyl)-anilin；3-(p-Aminophenyl)propylchlorid；4-(3-Chloropropyl)-anilin；Benzenamine, 4-(3-chloropropyl)-；4-(3-chloropropyl)aniline
• CAS: 396124-51-9
• 化学式: C₉H₁₂ClN
• mdl: MFCD09744310
• 分子量: 169.654
• InChiKey: SZLGIQPBYMYKCI-UHFFFAOYSA-N

物化性质

• 沸点：
  291.6±15.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-氨基苯基)丙基氯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-[4-[3-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]propyl]-N-(2-hydroxyethyl)anilino]ethanol
  参考文献：
  名称：

  7-Substituted 5-Amino-2-(2-furyl)pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines as A_2A Adenosine Receptor Antagonists:  A Study on the Importance of Modifications at the Side Chain on the Activity and Solubility

  摘要：

  It was demonstrated in the early 1990s that adenosine exerts many physiological functions through the interaction with four different receptors, named A(1), A(2A), A(2B), and A(3). In the past few years, our group has been involved in the development of A(2A) antagonists, which led to the synthesis of SCH 58261 (1), the first potent and selective adenosine A(2A) antagonist, which has been widely used as a reference compound. In this paper, we present an extended series of pyrazolotriazolopyrimidines synthesized with the aim to investigate the influence of the substitutions on the pyrazole ring. The choice of the substituents was based on their capability to improve water solubility while retaining high affinity and selectivity at the human A(2A) adenosine receptor subtype. In this series, some structural characteristics that are important for activity, i.e., tricyclic structure, free amino group at 5-position, furan ring, and substituent at 7-position on the pyrazole moiety, have been maintained. We focused our attention on the nature of the phenyl ring substituent to improve water solubility. Following this strategy, we developed new compounds with good affinity and selectivity for A(2A) adenosine receptors, such as 8d (K-i 0.12 nM; hA(1)/hA(2A) ratio = 1025; R-m = 2.8), 8h (K-i 0.22; hA(1)/hA(2A) ratio = 9818; R-m = 3.4), 8i (K-i 0.18 nM; hA(1)/hA(2A) ratio = 994; R-m = 2.8), 8k (K-i 0.13 nM; hA(1)/hA(2A) ratio = 4430; R-m = 3.6), and 14b (K-i 0.19 nM; hA(1)/hA(2A) ratio = 2273; R-m = 2.7). All the new synthesized compounds have no significant interaction with either-A(2B) or A(3) receptor subtypes. This new series of compounds deeply enlightens some structural requirements to display high affinity and selectivity for the A(2A) adenosine receptor subtype, although our goal of identifying new compounds with increased water solubility was not completely achieved. On this basis, other strategies will be devised to improve this class of compounds with a profile that appears to be promising for treatment of neurodegenerative disorders, such as Parkinson's disease.

  DOI：

  10.1021/jm010924c
• 作为产物：
  描述：

  1-氯-3-苯基丙烷 在 10percent Pd/C 氢气 、 硝酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 3-(4-氨基苯基)丙基氯
  参考文献：
  名称：

  7-Substituted 5-Amino-2-(2-furyl)pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines as A_2A Adenosine Receptor Antagonists:  A Study on the Importance of Modifications at the Side Chain on the Activity and Solubility

  摘要：

  It was demonstrated in the early 1990s that adenosine exerts many physiological functions through the interaction with four different receptors, named A(1), A(2A), A(2B), and A(3). In the past few years, our group has been involved in the development of A(2A) antagonists, which led to the synthesis of SCH 58261 (1), the first potent and selective adenosine A(2A) antagonist, which has been widely used as a reference compound. In this paper, we present an extended series of pyrazolotriazolopyrimidines synthesized with the aim to investigate the influence of the substitutions on the pyrazole ring. The choice of the substituents was based on their capability to improve water solubility while retaining high affinity and selectivity at the human A(2A) adenosine receptor subtype. In this series, some structural characteristics that are important for activity, i.e., tricyclic structure, free amino group at 5-position, furan ring, and substituent at 7-position on the pyrazole moiety, have been maintained. We focused our attention on the nature of the phenyl ring substituent to improve water solubility. Following this strategy, we developed new compounds with good affinity and selectivity for A(2A) adenosine receptors, such as 8d (K-i 0.12 nM; hA(1)/hA(2A) ratio = 1025; R-m = 2.8), 8h (K-i 0.22; hA(1)/hA(2A) ratio = 9818; R-m = 3.4), 8i (K-i 0.18 nM; hA(1)/hA(2A) ratio = 994; R-m = 2.8), 8k (K-i 0.13 nM; hA(1)/hA(2A) ratio = 4430; R-m = 3.6), and 14b (K-i 0.19 nM; hA(1)/hA(2A) ratio = 2273; R-m = 2.7). All the new synthesized compounds have no significant interaction with either-A(2B) or A(3) receptor subtypes. This new series of compounds deeply enlightens some structural requirements to display high affinity and selectivity for the A(2A) adenosine receptor subtype, although our goal of identifying new compounds with increased water solubility was not completely achieved. On this basis, other strategies will be devised to improve this class of compounds with a profile that appears to be promising for treatment of neurodegenerative disorders, such as Parkinson's disease.

  DOI：

  10.1021/jm010924c

文献信息

• Basic ethers of 2-anilinobenzothiazoles and 2-anilinobenzoxazoles as potential antidepressants
  作者：C. J. Sharpe、P. J. Palmer、D. E. Evans、G. R. Brown、Gillian King、R. S. Shadbolt、R. B. Trigg、R. J. Ward、A. Ashford、Janet W. Ross

  DOI：10.1021/jm00275a022

  日期：1972.5
• v. Braun; Deutsch, Chemische Berichte, 1912, vol. 45, p. 2511
  作者：v. Braun、Deutsch

  DOI：——

  日期：——