2-(4-chlorophenyl)-6-propoxyimiodazo<1,2-b>pyridazine | 3748-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-chlorophenyl)-6-propoxyimiodazo<1,2-b>pyridazine
• 英文别名: 2-(4-chloro-phenyl)-6-propoxy-imidazo[1,2-b]pyridazine；6-Propyloxy-2-(4-chlorphenyl)imidazo<1,2-b>pyridazin；Imidazo[1,2-b]pyridazine,2-(4-chlorophenyl)-6-propoxy-；2-(4-chlorophenyl)-6-propoxyimidazo[1,2-b]pyridazine
• CAS: 3748-69-4
• 化学式: C₁₅H₁₄ClN₃O
• 分子量: 287.749
• InChiKey: NOOWYAXZOIEDIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-羟甲基苯甲酰胺 、 2-(4-chlorophenyl)-6-propoxyimiodazo<1,2-b>pyridazine 在 硫酸 、 溶剂黄146 作用下， 反应 24.0h， 以52%的产率得到N-[[2-(4-chlorophenyl)-6-propoxyimidazo[1,2-b]pyridazin-3-yl]methyl]benzamide
  参考文献：
  名称：

  Syntheses, pharmacological evaluation and molecular modelling of substituted 6-alkoxyimidazo[1,2-b]pyridazines as new ligands for the benzodiazepine receptor

  摘要：

  A series of 2,3-disubstituted-6-alkoxyimidazo[1,2-b] has been synthesized and evaluated for in vitro affinity for the benzodiazepine receptor (BZR). 3-(Benzamidomethyl or substituted benzamidomethyl)-6-methoxy-2-(3,4-methylenedioxyphenyl)imidazo[1,2-b]pyridazines were found to be the most potent BZR ligands (eg, 4a, IC50 7 nM; 4e, IC50 14 nM; 4v, IC50 8 nM). Imidazo[1,2-b]pyridazines unsubstituted in the 3-position, or containing builder alkoxy groups in the 6-position, were found to bind less strongly to the BZR. Selected compounds from the series were identified from in vitro GABA-shift experiments as BZR agonists. Molecular modelling has been employed to identify the common pharmacophoric points of lipophilic and hydrogen bonding, ligand-receptor interaction and areas of steric hindrance for these substituted imidazo[1,2-b]pyridazines at the BZR.

  DOI：

  10.1016/0223-5234(96)85873-9
• 作为产物：
  描述：

  2'-溴-4-氯苯乙酮 、 6-丙氧基哒嗪-3-胺 在 碳酸氢钠 作用下， 生成 2-(4-chlorophenyl)-6-propoxyimiodazo<1,2-b>pyridazine
  参考文献：
  名称：

  Syntheses, pharmacological evaluation and molecular modelling of substituted 6-alkoxyimidazo[1,2-b]pyridazines as new ligands for the benzodiazepine receptor

  摘要：

  A series of 2,3-disubstituted-6-alkoxyimidazo[1,2-b] has been synthesized and evaluated for in vitro affinity for the benzodiazepine receptor (BZR). 3-(Benzamidomethyl or substituted benzamidomethyl)-6-methoxy-2-(3,4-methylenedioxyphenyl)imidazo[1,2-b]pyridazines were found to be the most potent BZR ligands (eg, 4a, IC50 7 nM; 4e, IC50 14 nM; 4v, IC50 8 nM). Imidazo[1,2-b]pyridazines unsubstituted in the 3-position, or containing builder alkoxy groups in the 6-position, were found to bind less strongly to the BZR. Selected compounds from the series were identified from in vitro GABA-shift experiments as BZR agonists. Molecular modelling has been employed to identify the common pharmacophoric points of lipophilic and hydrogen bonding, ligand-receptor interaction and areas of steric hindrance for these substituted imidazo[1,2-b]pyridazines at the BZR.

  DOI：

  10.1016/0223-5234(96)85873-9

文献信息

• 2-Phenylimidazo[1,2-b]pyridazine derivatives highly active against Haemonchus contortus
  作者：Abdelselam Ali、Teresa Cablewski、Craig L. Francis、Ashit K. Ganguly、Roger M. Sargent、David G. Sawutz、Kevin N. Winzenberg

  DOI：10.1016/j.bmcl.2011.05.096

  日期：2011.7

  A series of 2-phenylimidazo[1,2-b]pyridazine derivatives were synthesized and evaluated for their in vitro anthelmintic activity against Haemonchus contortus. The most active compounds had in vitro LD(99) values of 30 nM, which is comparable to that of the benchmark commercial nematocide, Ivermectin. (C) 2011 Elsevier Ltd. All rights reserved.
• Syntheses, pharmacological evaluation and molecular modelling of substituted 6-alkoxyimidazo[1,2-b]pyridazines as new ligands for the benzodiazepine receptor
  作者：PW Harrison、GB Barlin、LP Davies、SJ Ireland、P Mátyus、MG Wong

  DOI：10.1016/0223-5234(96)85873-9

  日期：1996.1

  A series of 2,3-disubstituted-6-alkoxyimidazo[1,2-b] has been synthesized and evaluated for in vitro affinity for the benzodiazepine receptor (BZR). 3-(Benzamidomethyl or substituted benzamidomethyl)-6-methoxy-2-(3,4-methylenedioxyphenyl)imidazo[1,2-b]pyridazines were found to be the most potent BZR ligands (eg, 4a, IC50 7 nM; 4e, IC50 14 nM; 4v, IC50 8 nM). Imidazo[1,2-b]pyridazines unsubstituted in the 3-position, or containing builder alkoxy groups in the 6-position, were found to bind less strongly to the BZR. Selected compounds from the series were identified from in vitro GABA-shift experiments as BZR agonists. Molecular modelling has been employed to identify the common pharmacophoric points of lipophilic and hydrogen bonding, ligand-receptor interaction and areas of steric hindrance for these substituted imidazo[1,2-b]pyridazines at the BZR.