(6-氨基吡嗪-3-基)(苯基)甲酮 | 146233-35-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (6-氨基吡嗪-3-基)(苯基)甲酮
• 英文名称: 3-amino-6-benzoylpyridazine
• 英文别名: 6-amino-3-benzoylpyridazine；(6-Aminopyridazin-3-YL)(phenyl)methanone；(6-aminopyridazin-3-yl)-phenylmethanone
• CAS: 146233-35-4
• 化学式: C₁₁H₉N₃O
• mdl: MFCD08236853
• 分子量: 199.212
• InChiKey: KZKHCQBIMPVXAH-UHFFFAOYSA-N

物化性质

• 沸点：
  468.8±30.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6-氨基吡嗪-3-基)(苯基)甲酮 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 2-[3-benzoyl-6-(toluene-4-sulfonylimino)-6H-pyridazin-1-yl]-2-phenylacetamide
  参考文献：
  名称：

  Imidazo[1,2-b]pyridazines, Novel Nucleus with Potent and Broad Spectrum Activity against Human Picornaviruses:  Design, Synthesis, and Biological Evaluation

  摘要：

  A novel structural class of picornavirus inhibitors comprising an imidazo[1,2-b]pyridazine nucleus was discovered. 2-Aminoimidazo[1,2-b]pyridazines (6d, (E/Z)-7b, (E)-7d, (Z)-7d, (El Z)-8b, (E)-10b, (E)-13a, (Z)-13a, (E)-13b, (Z)-13b, (E)-13c, and (Z)-13c) were designed and synthesized in an effort to identify potent broad spectrum antirhinoviral agents. A practical synthetic route to this chemical scaffold has been developed. The target compounds were evaluated in a plaque reduction assay and in a cytopathic effect assay. Our preliminary SAR studies highlight the minimum structural features required for antirhinovirus activity. Our data suggest that the nature of the linker between the phenyl and the imidazopyridazine moieties has a significant influence on the activity of these compounds. Oximes are slightly better than vinyl carboxamides at this position. The oximes are the most potent analogues against human rhinovirus 14 (HRV-14), and at the concentrations evaluated, no apparent cellular toxicity is noted. Furthermore, the E geometry appears to be a key element for activity; the Z isomer leads to a considerable loss in potency. Of particular interest, analogue 7b exhibits potent broad-spectrum antirhinoviral and antienteroviral activity when evaluated against a panel of seven additional rhino- and enteroviruses. The chemistry and the biological evaluations are discussed.

  DOI：

  10.1021/jm020583i
• 作为产物：
  描述：

  6-氯哒嗪-3-羧酸 在 三氯化铝 、 氯化亚砜 、 氨 作用下， 反应 44.0h， 生成 (6-氨基吡嗪-3-基)(苯基)甲酮
  参考文献：
  名称：

  咪唑并[1,2 - b ]哒嗪-2-氨基甲酸甲酯及相关化合物作为潜在的抗丝虫剂

  摘要：

  合成了一系列咪唑并[1,2- b ]哒嗪，用于抗丝虫性评估。制备的化合物包括6-苯甲酰咪唑并[1,2 - b ]哒嗪-2-氨基甲酸甲酯（12），6-苯甲酰基-2-叔丁基咪唑并[1,2- b ]哒嗪（13），甲基6-（4 -氟苯甲酰基）咪唑并[1,2 - b ]哒嗪-2-氨基甲酸酯（14）和6-（2-噻吩基羰基羰基）咪唑并[1,2 - b ]哒嗪-2-氨基甲酸酯（15），它们是氮杂类似物。驱虫药甲苯达唑，氟苯达唑和诺卡达唑。另外，制备了一系列的2-叔丁基咪唑[1,2- b描述了]-哒嗪-6-羧酸衍生物。2-叔丁基-6-甲基咪唑并[1,2- b ]哒嗪的亲电溴化和碘化取代得到3-卤代衍生物。还制备了6-（4-氟苯甲酰基）哒嗪-3-氨基甲酸甲酯以用于抗丝虫评价。这些化合物均不具有针对吉氏布鲁氏菌或棘阿米巴蛋白菌感染的显着抗丝虫活性。

  DOI：

  10.1002/jhet.5570290636

文献信息

• Methyl imidazo[1,2-<i>b</i>]pyridazine-2-carbamates and related compounds as potential antifilarial agents
  作者：Alaa E. Mourad、Dean S. Wise、Leroy B. Townsend

  DOI：10.1002/jhet.5570290636

  日期：1992.10

  A series of imidazo[1,2-b]pyridazines have been synthesized for antifilarial evaluation. The compounds prepared include methyl 6-benzoylimidazo[1,2-b]pyridazine-2-carbamate (12), 6-benzoyl-2-t-butylimidazo[1,2-b]pyridazine (13), methyl 6-(4-fluorobenzoyl)imidazo[1,2-b]pyridazine-2-carbamate (14), and methyl 6-(2-thienylcarbonylcarbonyl)imidazo[1,2-b]pyridazine-2-carbamate (15) which are aza analogs

  合成了一系列咪唑并[1,2- b ]哒嗪，用于抗丝虫性评估。制备的化合物包括6-苯甲酰咪唑并[1,2 - b ]哒嗪-2-氨基甲酸甲酯（12），6-苯甲酰基-2-叔丁基咪唑并[1,2- b ]哒嗪（13），甲基6-（4 -氟苯甲酰基）咪唑并[1,2 - b ]哒嗪-2-氨基甲酸酯（14）和6-（2-噻吩基羰基羰基）咪唑并[1,2 - b ]哒嗪-2-氨基甲酸酯（15），它们是氮杂类似物。驱虫药甲苯达唑，氟苯达唑和诺卡达唑。另外，制备了一系列的2-叔丁基咪唑[1,2- b描述了]-哒嗪-6-羧酸衍生物。2-叔丁基-6-甲基咪唑并[1,2- b ]哒嗪的亲电溴化和碘化取代得到3-卤代衍生物。还制备了6-（4-氟苯甲酰基）哒嗪-3-氨基甲酸甲酯以用于抗丝虫评价。这些化合物均不具有针对吉氏布鲁氏菌或棘阿米巴蛋白菌感染的显着抗丝虫活性。
• Imidazo[1,2-<i>b</i>]pyridazines, Novel Nucleus with Potent and Broad Spectrum Activity against Human Picornaviruses:  Design, Synthesis, and Biological Evaluation
  作者：Chafiq Hamdouchi、Concha Sanchez-Martinez、Joseph Gruber、Miriam del Prado、Javier Lopez、Almudena Rubio、Beverly A. Heinz

  DOI：10.1021/jm020583i

  日期：2003.9.1

  A novel structural class of picornavirus inhibitors comprising an imidazo[1,2-b]pyridazine nucleus was discovered. 2-Aminoimidazo[1,2-b]pyridazines (6d, (E/Z)-7b, (E)-7d, (Z)-7d, (El Z)-8b, (E)-10b, (E)-13a, (Z)-13a, (E)-13b, (Z)-13b, (E)-13c, and (Z)-13c) were designed and synthesized in an effort to identify potent broad spectrum antirhinoviral agents. A practical synthetic route to this chemical scaffold has been developed. The target compounds were evaluated in a plaque reduction assay and in a cytopathic effect assay. Our preliminary SAR studies highlight the minimum structural features required for antirhinovirus activity. Our data suggest that the nature of the linker between the phenyl and the imidazopyridazine moieties has a significant influence on the activity of these compounds. Oximes are slightly better than vinyl carboxamides at this position. The oximes are the most potent analogues against human rhinovirus 14 (HRV-14), and at the concentrations evaluated, no apparent cellular toxicity is noted. Furthermore, the E geometry appears to be a key element for activity; the Z isomer leads to a considerable loss in potency. Of particular interest, analogue 7b exhibits potent broad-spectrum antirhinoviral and antienteroviral activity when evaluated against a panel of seven additional rhino- and enteroviruses. The chemistry and the biological evaluations are discussed.