2-chloromethyl-4-phenyl-2H-phthalazin-1-one | 92427-81-1

• 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: 2-chloromethyl-4-phenyl-2H-phthalazin-1-one
• 英文别名: (4-phenylphthalazin-1-one-2-yl)methyl chloride；2-Chlormethyl-4-phenyl-2H-phthalazinon-(1)；2-chloromethyl-4-phenyl-2H-phthalazin-1-one
• CAS: 92427-81-1
• 化学式: C₁₅H₁₁ClN₂O
• 分子量: 270.718
• InChiKey: BZCMLGBRJABNQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-chloromethyl-4-phenyl-2H-phthalazin-1-one 、 (2R,3R,4R)-2-(羟基甲基)-3,4-二氢-2H-吡喃-3,4-二醇 在 四丁基碘化铵 、 二正丁基氧化锡 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 0.5h， 以31%的产率得到3-O-(4-phenylphthalazin-1(2H)-one-2-ylmethyl)-D-galactal
  参考文献：
  名称：

  Selective Galectin‐8N Ligands: The Design and Synthesis of Phthalazinone‐ d ‐Galactals

  摘要：

  AbstractLigand selectivity among the highly conserved galectins has been an ever‐challenging objective. For galectin‐8, a protein prevalent in both pathology and tissue distribution, we report phthalazinone‐galactals that show excellent selectivity for the galectin‐8N‐terminal domain. A dissection of structure–activity relationships of the phthalazinone and an extensive molecular dynamics meta‐analysis accompany the discovery of the selective galectin‐8N ligands presented here. These selective compounds will facilitate the study of galectin‐8 biology and may have pharmaceutical relevance in the wide range of galectin‐8 associated pathologies.

  DOI：

  10.1002/cmdc.202100575
• 作为产物：
  描述：

  sodium formaldehyde bisulfite 、 4-苯基-1(2H)-酞嗪酮 在 氯化亚砜 作用下， 反应 16.0h， 以43%的产率得到2-chloromethyl-4-phenyl-2H-phthalazin-1-one
  参考文献：
  名称：

  Selective Galectin‐8N Ligands: The Design and Synthesis of Phthalazinone‐ d ‐Galactals

  摘要：

  AbstractLigand selectivity among the highly conserved galectins has been an ever‐challenging objective. For galectin‐8, a protein prevalent in both pathology and tissue distribution, we report phthalazinone‐galactals that show excellent selectivity for the galectin‐8N‐terminal domain. A dissection of structure–activity relationships of the phthalazinone and an extensive molecular dynamics meta‐analysis accompany the discovery of the selective galectin‐8N ligands presented here. These selective compounds will facilitate the study of galectin‐8 biology and may have pharmaceutical relevance in the wide range of galectin‐8 associated pathologies.

  DOI：

  10.1002/cmdc.202100575