2-[2-Oxo-4-(thieno[3,2-b]pyridine-2-sulfonyl)-piperazin-1-ylmethyl]-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester | 1028312-60-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[2-Oxo-4-(thieno[3,2-b]pyridine-2-sulfonyl)-piperazin-1-ylmethyl]-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 2-[(2-oxo-4-thieno[3,2-b]pyridin-2-ylsulfonylpiperazin-1-yl)methyl]pyrrolo[3,2-c]pyridine-1-carboxylate
• CAS: 1028312-60-8
• 化学式: C₂₄H₂₅N₅O₅S₂
• 分子量: 527.625
• InChiKey: OPARIECMTPUMLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[2-Oxo-4-(thieno[3,2-b]pyridine-2-sulfonyl)-piperazin-1-ylmethyl]-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-(1H-Pyrrolo[3,2-c]pyridin-2-ylmethyl)-4-(thieno[3,2-b]pyridine-2-sulfonyl)-piperazin-2-one
  参考文献：
  名称：

  Discovery of an Orally Efficacious Inhibitor of Coagulation Factor Xa Which Incorporates a Neutral P₁ Ligand

  摘要：

  The discovery and SAR of ketopiperazino methylazaindole factor Xa inhibitors are described. Structureactivity data suggesting that this class of inhibitors does not bind in the canonical mode were confirmed by an X-ray crystal structure showing the neutral haloaromatic bound in the S, subsite. The most potent azaindole, 33 (RPR209685), is selective against related serine proteases and attains higher levels of exposure upon oral dosing than comparable benzamidines and benzamidine isosteres. Compound 33 was efficacious in the canine AV model of thrombosis.

  DOI：

  10.1021/jm020384z
• 作为产物：
  描述：

  4-氨基-3-碘吡啶 在 钯 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 甲酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.67h， 生成 2-[2-Oxo-4-(thieno[3,2-b]pyridine-2-sulfonyl)-piperazin-1-ylmethyl]-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Discovery of an Orally Efficacious Inhibitor of Coagulation Factor Xa Which Incorporates a Neutral P₁ Ligand

  摘要：

  The discovery and SAR of ketopiperazino methylazaindole factor Xa inhibitors are described. Structureactivity data suggesting that this class of inhibitors does not bind in the canonical mode were confirmed by an X-ray crystal structure showing the neutral haloaromatic bound in the S, subsite. The most potent azaindole, 33 (RPR209685), is selective against related serine proteases and attains higher levels of exposure upon oral dosing than comparable benzamidines and benzamidine isosteres. Compound 33 was efficacious in the canine AV model of thrombosis.

  DOI：

  10.1021/jm020384z