methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-N-(tert-butoxycarbonylsulfamoyl)-N-{[(3-cyanophenyl)(methyl)carbamoyl]methyl}anthranilate | 540765-43-3

• 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: methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-N-(tert-butoxycarbonylsulfamoyl)-N-{[(3-cyanophenyl)(methyl)carbamoyl]methyl}anthranilate
• CAS: 540765-43-3
• 化学式: C₃₃H₄₃N₅O₁₀S
• 分子量: 701.798
• InChiKey: RZRUBIRRSPJCJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  49.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  184.88
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-N-(tert-butoxycarbonylsulfamoyl)-N-{[(3-cyanophenyl)(methyl)carbamoyl]methyl}anthranilate 在 盐酸 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 119.63h， 生成 6-[(1-acetimidoyl-4-piperidyl)oxy]-1-{[(3-amidinophenyl)(methyl)carbamoyl]methyl}-1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide 2.2-hydrochloride
  参考文献：
  名称：

  Design, synthesis and biological activity of YM-60828 derivatives. Part 2: potent and orally-bioavailable factor Xa inhibitors based on benzothiadiazine-4-one template

  摘要：

  Compound YM-60828 was previously characterized in our laboratory as a potent, selective and orally-bioavailable Factor Xa (FXa) inhibitor. The L-shape conformation of this compound in the active site of FXa was recognized as an important factor in displaying its FXa inhibitory activity. This led to the exploration of conformationally restricted cyclic scaffolds bearing a similar active conformation. The current study investigated a novel series of benzothiadiazine-4-one based compounds as FXa inhibitors. Structure-activity relationship (SAR) investigations revealed some potent FXa inhibitors that were selected for further in vitro and ex vivo anticoagulant studies. Among them, compound 6j (YM-169920) was proved to be most effective anticoagulant in this series. The synthesis and SAR in addition to docking studies of this class of inhibitors are described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00462-5
• 作为产物：
  描述：

  2-氨基-5-羟基苯甲酸甲基 在 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 乙腈 为溶剂， 反应 109.0h， 生成 methyl 5-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]-N-(tert-butoxycarbonylsulfamoyl)-N-{[(3-cyanophenyl)(methyl)carbamoyl]methyl}anthranilate
  参考文献：
  名称：

  Design, synthesis and biological activity of YM-60828 derivatives. Part 2: potent and orally-bioavailable factor Xa inhibitors based on benzothiadiazine-4-one template

  摘要：

  Compound YM-60828 was previously characterized in our laboratory as a potent, selective and orally-bioavailable Factor Xa (FXa) inhibitor. The L-shape conformation of this compound in the active site of FXa was recognized as an important factor in displaying its FXa inhibitory activity. This led to the exploration of conformationally restricted cyclic scaffolds bearing a similar active conformation. The current study investigated a novel series of benzothiadiazine-4-one based compounds as FXa inhibitors. Structure-activity relationship (SAR) investigations revealed some potent FXa inhibitors that were selected for further in vitro and ex vivo anticoagulant studies. Among them, compound 6j (YM-169920) was proved to be most effective anticoagulant in this series. The synthesis and SAR in addition to docking studies of this class of inhibitors are described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00462-5