5-hydrazosulfonylbenzene-1,3-carboxylic acid dimethyl ester | 926291-89-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-hydrazosulfonylbenzene-1,3-carboxylic acid dimethyl ester
• 英文别名: Dimethyl 5-(hydrazinesulfonyl)benzene-1,3-dicarboxylate
• CAS: 926291-89-6
• 化学式: C₁₀H₁₂N₂O₆S
• 分子量: 288.281
• InChiKey: UVYPTEJLEBAXKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-hydrazosulfonylbenzene-1,3-carboxylic acid dimethyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 37.0h， 生成 (E)-5-[1-(4-butyloxy-3-methoxyphenyl)-1-phenylmethylene]-sulfohydrazono-isophthalic acid
  参考文献：
  名称：

  Pharmacophore-Based Design of Sphingosine 1-phosphate-3 Receptor Antagonists That Include a 3,4-Dialkoxybenzophenone Scaffold

  摘要：

  Sphingosine 1-phosphate (S1P) receptors are G-protein-coupled receptors. Among the five identified subtypes S1P(1)-5, the S1P(3) receptor expressed on vascular endothelial cells has been shown to play an important role in cell proliferation, migration, and inflammation. A pharmacophore-based database search was used to identify a potent scaffold for an S1P(3) receptor antagonist by common feature-based alignment and further validated using the GUner-Henry (GH) scoring method. Assumed excluded volumes were merged into this model to evaluate the steric effect with the S1P(3) receptor. Three commercially available compounds were identified as S1P(3) receptor antagonists, with IC50 values < 5 mu M. The synthesis of further derivatives revealed that the 3,4-dialkoxybenzophenone scaffold is a potent component of an S1P(3) receptor antagonist. Our results indicate that pharmacophore-based design of S1P(3) receptor antagonists can be used to expand the possibility of structural modification through scaffold-hopping based on a database search.

  DOI：

  10.1021/jm060834d
• 作为产物：
  描述：

  5-(氯磺酰基)异邻苯二甲酸二甲酯 在 一水合肼 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 6.0h， 以56%的产率得到5-hydrazosulfonylbenzene-1,3-carboxylic acid dimethyl ester
  参考文献：
  名称：

  Pharmacophore-Based Design of Sphingosine 1-phosphate-3 Receptor Antagonists That Include a 3,4-Dialkoxybenzophenone Scaffold

  摘要：

  Sphingosine 1-phosphate (S1P) receptors are G-protein-coupled receptors. Among the five identified subtypes S1P(1)-5, the S1P(3) receptor expressed on vascular endothelial cells has been shown to play an important role in cell proliferation, migration, and inflammation. A pharmacophore-based database search was used to identify a potent scaffold for an S1P(3) receptor antagonist by common feature-based alignment and further validated using the GUner-Henry (GH) scoring method. Assumed excluded volumes were merged into this model to evaluate the steric effect with the S1P(3) receptor. Three commercially available compounds were identified as S1P(3) receptor antagonists, with IC50 values < 5 mu M. The synthesis of further derivatives revealed that the 3,4-dialkoxybenzophenone scaffold is a potent component of an S1P(3) receptor antagonist. Our results indicate that pharmacophore-based design of S1P(3) receptor antagonists can be used to expand the possibility of structural modification through scaffold-hopping based on a database search.

  DOI：

  10.1021/jm060834d

文献信息

• Pharmacophore-Based Design of Sphingosine 1-phosphate-3 Receptor Antagonists That Include a 3,4-Dialkoxybenzophenone Scaffold
  作者：Yuuki Koide、Kazuhiro Uemoto、Takeshi Hasegawa、Tomoyuki Sada、Akira Murakami、Hiroshi Takasugi、Atsuko Sakurai、Naoki Mochizuki、Atsuo Takahashi、Atsushi Nishida

  DOI：10.1021/jm060834d

  日期：2007.2.8

  Sphingosine 1-phosphate (S1P) receptors are G-protein-coupled receptors. Among the five identified subtypes S1P(1)-5, the S1P(3) receptor expressed on vascular endothelial cells has been shown to play an important role in cell proliferation, migration, and inflammation. A pharmacophore-based database search was used to identify a potent scaffold for an S1P(3) receptor antagonist by common feature-based alignment and further validated using the GUner-Henry (GH) scoring method. Assumed excluded volumes were merged into this model to evaluate the steric effect with the S1P(3) receptor. Three commercially available compounds were identified as S1P(3) receptor antagonists, with IC50 values < 5 mu M. The synthesis of further derivatives revealed that the 3,4-dialkoxybenzophenone scaffold is a potent component of an S1P(3) receptor antagonist. Our results indicate that pharmacophore-based design of S1P(3) receptor antagonists can be used to expand the possibility of structural modification through scaffold-hopping based on a database search.