4-amino-3-chloro-1-(2,3-dideoxy-β-D-glycero-pentofuranosyl)pyridazin-6-one | 156549-62-1

• 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: 4-amino-3-chloro-1-(2,3-dideoxy-β-D-glycero-pentofuranosyl)pyridazin-6-one
• 英文别名: 5-amino-6-chloro-2-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyridazin-3-one；5-amino-6-chloro-2-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyridazin-3-one
• CAS: 156549-62-1
• 化学式: C₉H₁₂ClN₃O₃
• 分子量: 245.666
• InChiKey: SEKUSAPFAQZYLH-YLWLKBPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  88.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-3-chloro-1-(2,3-dideoxy-β-D-glycero-pentofuranosyl)pyridazin-6-one 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以90%的产率得到4-amino-1-(2,3-dideoxy-β-D-glycero-pentofuranosyl)pyridazin-6-one
  参考文献：
  名称：

  Synthesis of 2′,3′-Dideoxy- and 3′-Azido-2′,3′-dideoxy-pyridazine Nucleosides as Potential Antiviral Agents

  摘要：

  The synthesis of 4-methoxy-, 4-amino-3-chloro-, and 4-amino-1-(2,3-dideoxy-beta-D-glycero-pentofuranosyl)pyridazin-6-one nucleosides, 6, 19 and 20 is described. The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of 3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-beta-D-erythro-pentofuranosyl)pyridazin-6-one (13) in 67% and its alpha-anomer 14 in 12% yield, (r)espectively. A series of 3'-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1- (3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive.

  DOI：

  10.1080/15257779408013255
• 作为产物：
  描述：

  4-amino-3-chloro-1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)pyridazin-6-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 以67%的产率得到4-amino-3-chloro-1-(2,3-dideoxy-β-D-glycero-pentofuranosyl)pyridazin-6-one
  参考文献：
  名称：

  Synthesis of 2′,3′-Dideoxy- and 3′-Azido-2′,3′-dideoxy-pyridazine Nucleosides as Potential Antiviral Agents

  摘要：

  The synthesis of 4-methoxy-, 4-amino-3-chloro-, and 4-amino-1-(2,3-dideoxy-beta-D-glycero-pentofuranosyl)pyridazin-6-one nucleosides, 6, 19 and 20 is described. The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of 3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-beta-D-erythro-pentofuranosyl)pyridazin-6-one (13) in 67% and its alpha-anomer 14 in 12% yield, (r)espectively. A series of 3'-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1- (3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive.

  DOI：

  10.1080/15257779408013255

文献信息

• Synthesis of 2′,3′-Dideoxy- and 3′-Azido-2′,3′-dideoxy-pyridazine Nucleosides as Potential Antiviral Agents
  作者：Biserka Kasnar、Dean S. Wise、Louis S. Kucera、John C. Drach、Leroy B. Townsend

  DOI：10.1080/15257779408013255

  日期：1994.3

  The synthesis of 4-methoxy-, 4-amino-3-chloro-, and 4-amino-1-(2,3-dideoxy-beta-D-glycero-pentofuranosyl)pyridazin-6-one nucleosides, 6, 19 and 20 is described. The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of 3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-beta-D-erythro-pentofuranosyl)pyridazin-6-one (13) in 67% and its alpha-anomer 14 in 12% yield, (r)espectively. A series of 3'-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1- (3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive.