2-(2-chlorophenyl)-6-hydroxypyridazin-3(2H)-one | 53674-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(2-chlorophenyl)-6-hydroxypyridazin-3(2H)-one
• 英文别名: 2-(2-chloro-phenyl)-6-hydroxy-2H-pyridazin-3-one；3-Hydroxy-6-oxo-1-(2-chlor-phenyl)-1.6-dihydro-pyridazin；1-(2-Chlorphenyl)-3-hydroxypyridazon-6；Pyridazine-3,6(1H,2H)-dione, 1-(2-chlorophenyl)-；2-(2-chlorophenyl)-1H-pyridazine-3,6-dione
• CAS: 53674-27-4
• 化学式: C₁₀H₇ClN₂O₂
• 分子量: 222.631
• InChiKey: FJAFBNURTGHKCR-UHFFFAOYSA-N

物化性质

• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-chlorophenyl)-6-hydroxypyridazin-3(2H)-one 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium hydride 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 、 肼 、 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 25.0h， 生成 6-[(3-Aminopropyl)(2-chlorophenyl)amino]-2-(2-chlorophenyl)-2,3-dihydropyridazin-3-one
  参考文献：
  名称：

  p38 MAP kinase inhibitors. Part 6: 2-Arylpyridazin-3-ones as templates for inhibitor design

  摘要：

  p38 inhibitors based on 3,4-dihydropyrido[4,3-d]pyrimidazin-2-one template were synthesized and their SAR explored. Benchmark compounds 30, 35, and 36 were found to be potent against the enzyme. Crystal structure of p38 in complex with 30 indicated a key pi-stacking interaction with the pendant tyrosine residue-35 in the glycine-rich loop.

  DOI：

  10.1016/j.bmcl.2006.08.074
• 作为产物：
  描述：

  马来酸酐 、 (2-氯苯基)-肼 以 乙醇 为溶剂， 反应 12.0h， 以70%的产率得到2-(2-chlorophenyl)-6-hydroxypyridazin-3(2H)-one
  参考文献：
  名称：

  p38 MAP kinase inhibitors. Part 6: 2-Arylpyridazin-3-ones as templates for inhibitor design

  摘要：

  p38 inhibitors based on 3,4-dihydropyrido[4,3-d]pyrimidazin-2-one template were synthesized and their SAR explored. Benchmark compounds 30, 35, and 36 were found to be potent against the enzyme. Crystal structure of p38 in complex with 30 indicated a key pi-stacking interaction with the pendant tyrosine residue-35 in the glycine-rich loop.

  DOI：

  10.1016/j.bmcl.2006.08.074

文献信息

• Synthesis and biological evaluation of new 6-hydroxypyridazinone benzisoxazoles: Potential multi-receptor-targeting atypical antipsychotics
  作者：Xudong Cao、Yin Chen、Yifang Zhang、Yinli Qiu、Minquan Yu、Xiangqing Xu、Xin Liu、Bi-Feng Liu、Guisen Zhang

  DOI：10.1016/j.ejmech.2016.09.008

  日期：2016.11

  In recent years, multi-targeting directed ligands have attracted great interest as possible new atypical antipsychotics. Combinations of dopamine and serotonin receptor ligands within single molecules might afford new therapeutic opportunities. Herein, we describe the synthesis of a novel series of 6-hydroxypyridazinone benzisoxazoles and their binding behaviors to different receptors in terms of atypical antipsychotic behaviors. The most potent compound (46) exhibited excellent affinities for certain receptors (D-2, K-i = 0.5 +/- 0.07 nM; 5-HT1A, K-i = 5.9 +/- 0.8 nM; 5-HT2A, K-i = 0.3 +/- 0.01 nM; 5-HT6, K-i = 0.5 +/- 0.04 nM) and combined with low affinities for the H-1, 5-HT2C, and adrenergic alpha(1) receptors. In contrast to risperidone, compound 46 exhibited a high cataleptic threshold; this may be useful in the development of a novel class of drugs treating schizophrenia. (C) 2016 Elsevier Masson SAS. All rights reserved.
• SIMAMURA, XIROSI;KOSEHGI, KODZI;YANAGINUMA, XIDEHYA
  作者：SIMAMURA, XIROSI、KOSEHGI, KODZI、YANAGINUMA, XIDEHYA

  DOI：——

  日期：——
• p38 MAP kinase inhibitors. Part 6: 2-Arylpyridazin-3-ones as templates for inhibitor design
  作者：Swaminathan R. Natarajan、Stephen T. Heller、Kiyean Nam、Suresh B. Singh、Giovanna Scapin、Sangita Patel、James E. Thompson、Catherine E. Fitzgerald、Stephen J. O’Keefe

  DOI：10.1016/j.bmcl.2006.08.074

  日期：2006.11

  p38 inhibitors based on 3,4-dihydropyrido[4,3-d]pyrimidazin-2-one template were synthesized and their SAR explored. Benchmark compounds 30, 35, and 36 were found to be potent against the enzyme. Crystal structure of p38 in complex with 30 indicated a key pi-stacking interaction with the pendant tyrosine residue-35 in the glycine-rich loop.