3-(4-chlorophenyl)hydrazono-1,2,3,4-tetrahydroquinoxalin-2-one | 269716-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-(4-chlorophenyl)hydrazono-1,2,3,4-tetrahydroquinoxalin-2-one
• 英文别名: 3-[2-(4-chlorophenyl)hydrazinyl]-1H-quinoxalin-2-one
• CAS: 269716-94-1
• 化学式: C₁₄H₁₁ClN₄O
• 分子量: 286.721
• InChiKey: CDUOHKZMODTQRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)hydrazono-1,2,3,4-tetrahydroquinoxalin-2-one 在 吡啶 、 五氯化磷 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 4-Chloro-2-(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]quinoxalin-1-one
  参考文献：
  名称：

  1,2,4-Triazolo[4,3-a]quinoxalin-1-one:  A Versatile Tool for the Synthesis of Potent and Selective Adenosine Receptor Antagonists

  摘要：

  4-Amino-6-benzylamino-1,2-dihydro-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-1-one (1) has been found to be an A(2A) versus A(1) selective antagonist (Colotta et al. Arch. Pharm. Pharm. Med. Chem. 1999,332, 39-41). In this paper some novel triazoloquinoxalin-1-ones 4-25 bearing different substituents on the 2-phenyl and/or 4-amino moiety of the parent 4-amino-1,2-dihydro-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-1-one (3) have been synthesized and tested in radioligand binding assays at bovine A(1) and A(2A) and cloned human A(3) adenosine receptors (AR). Moreover, the binding activities at the above-mentioned AR subtypes of the 1,4-dione parent compounds 26-31 and their 5-N-alkyl derivatives 33-37 were also evaluated. The substituent on the 2-phenyl ring exerted a different effect on AR subtypes, while replacement of a hydrogen atom of the 4-amino group with suitable substituents yielded selective A(1) or A(3) antagonists. Replacement of a hydrogen atom of the 4-NH2 with an acyl group, or replacement of the whole 4-NH2 with a 4-oxo moiety, shifted the binding activity toward the A(3) AR. The binding results allowed elucidation of the structural requirements for the binding of these novel tricyclic derivatives at each receptor subtype. In particular, A(1) and A(2A) binding required the presence of a proton donor group at position-4, while for A(3) affinity the presence of a proton acceptor in this same region was of paramount importance.

  DOI：

  10.1021/jm991096e
• 作为产物：
  描述：

  邻苯二胺 、 ethyl 2-chloro[(4-chlorophenyl)hydrazono]acetate 在 三乙胺 作用下， 以93%的产率得到3-(4-chlorophenyl)hydrazono-1,2,3,4-tetrahydroquinoxalin-2-one
  参考文献：
  名称：

  1,2,4-Triazolo[4,3-a]quinoxalin-1-one:  A Versatile Tool for the Synthesis of Potent and Selective Adenosine Receptor Antagonists

  摘要：

  4-Amino-6-benzylamino-1,2-dihydro-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-1-one (1) has been found to be an A(2A) versus A(1) selective antagonist (Colotta et al. Arch. Pharm. Pharm. Med. Chem. 1999,332, 39-41). In this paper some novel triazoloquinoxalin-1-ones 4-25 bearing different substituents on the 2-phenyl and/or 4-amino moiety of the parent 4-amino-1,2-dihydro-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-1-one (3) have been synthesized and tested in radioligand binding assays at bovine A(1) and A(2A) and cloned human A(3) adenosine receptors (AR). Moreover, the binding activities at the above-mentioned AR subtypes of the 1,4-dione parent compounds 26-31 and their 5-N-alkyl derivatives 33-37 were also evaluated. The substituent on the 2-phenyl ring exerted a different effect on AR subtypes, while replacement of a hydrogen atom of the 4-amino group with suitable substituents yielded selective A(1) or A(3) antagonists. Replacement of a hydrogen atom of the 4-NH2 with an acyl group, or replacement of the whole 4-NH2 with a 4-oxo moiety, shifted the binding activity toward the A(3) AR. The binding results allowed elucidation of the structural requirements for the binding of these novel tricyclic derivatives at each receptor subtype. In particular, A(1) and A(2A) binding required the presence of a proton donor group at position-4, while for A(3) affinity the presence of a proton acceptor in this same region was of paramount importance.

  DOI：

  10.1021/jm991096e

文献信息

• 1,2,4-Triazolo[4,3-<i>a</i>]quinoxalin-1-one:  A Versatile Tool for the Synthesis of Potent and Selective Adenosine Receptor Antagonists
  作者：Vittoria Colotta、Daniela Catarzi、Flavia Varano、Lucia Cecchi、Guido Filacchioni、Claudia Martini、Letizia Trincavelli、Antonio Lucacchini

  DOI：10.1021/jm991096e

  日期：2000.3.1

  4-Amino-6-benzylamino-1,2-dihydro-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-1-one (1) has been found to be an A(2A) versus A(1) selective antagonist (Colotta et al. Arch. Pharm. Pharm. Med. Chem. 1999,332, 39-41). In this paper some novel triazoloquinoxalin-1-ones 4-25 bearing different substituents on the 2-phenyl and/or 4-amino moiety of the parent 4-amino-1,2-dihydro-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-1-one (3) have been synthesized and tested in radioligand binding assays at bovine A(1) and A(2A) and cloned human A(3) adenosine receptors (AR). Moreover, the binding activities at the above-mentioned AR subtypes of the 1,4-dione parent compounds 26-31 and their 5-N-alkyl derivatives 33-37 were also evaluated. The substituent on the 2-phenyl ring exerted a different effect on AR subtypes, while replacement of a hydrogen atom of the 4-amino group with suitable substituents yielded selective A(1) or A(3) antagonists. Replacement of a hydrogen atom of the 4-NH2 with an acyl group, or replacement of the whole 4-NH2 with a 4-oxo moiety, shifted the binding activity toward the A(3) AR. The binding results allowed elucidation of the structural requirements for the binding of these novel tricyclic derivatives at each receptor subtype. In particular, A(1) and A(2A) binding required the presence of a proton donor group at position-4, while for A(3) affinity the presence of a proton acceptor in this same region was of paramount importance.