ethyl ({[(7-cyano-2-naphthyl)methyl][4-(4-methyl-1,4-diazepan-1-yl)phenyl]amino}sulfonyl)acetate | 714249-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: ethyl ({[(7-cyano-2-naphthyl)methyl][4-(4-methyl-1,4-diazepan-1-yl)phenyl]amino}sulfonyl)acetate
• CAS: 714249-31-7
• 化学式: C₂₈H₃₂N₄O₄S
• 分子量: 520.652
• InChiKey: JQKDTRDQUKZSOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  93.95
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl ({[(7-cyano-2-naphthyl)methyl][4-(4-methyl-1,4-diazepan-1-yl)phenyl]amino}sulfonyl)acetate 在 盐酸 、 ammonium acetate 作用下， 以 甲醇 、 氯仿 、 1,4-二氧六环 为溶剂， 反应 40.0h， 以40%的产率得到ethyl ({({7-[amino(imino)methyl]-2-naphthyl}methyl)[4-(4-methyl-1,4-diazepan-1-yl)phenyl]amino}sulfonyl)acetate acid 2.9 hydrochloride
  参考文献：
  名称：

  Orally active factor Xa inhibitor: synthesis and biological activity of masked amidines as prodrugs of novel 1,4-diazepane derivatives

  摘要：

  Factor Xa (fXa) is a serine protease, which plays a pivotal role in the coagulation cascade. To improve the oral anticoagulant activity of fXa inhibitors containing a 1,4-diazepane moiety as the P4 part, a prodrug strategy was examined. Among the compounds evaluated in this study, amidoxime prodrugs bearing an ester moiety, Such as compounds 21 and 30, showed effective oral anticoagulant activity in mice. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.046
• 作为产物：
  描述：

  tert-butyl 4-(4-nitrophenyl)-1,4-diazepane-1-carboxylate 在 palladium on activated charcoal 吡啶 、 氢气 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 38.0h， 生成 ethyl ({[(7-cyano-2-naphthyl)methyl][4-(4-methyl-1,4-diazepan-1-yl)phenyl]amino}sulfonyl)acetate
  参考文献：
  名称：

  Synthesis and biological activity of novel 1,4-diazepane derivatives as factor Xa inhibitor with potent anticoagulant and antithrombotic activity

  摘要：

  Factor Xa (fXa) is a serine protease involved in the coagulation cascade, which has received great interest as a potential target for the development of new antithrombotic drugs. Herein we report a novel series of fXa inhibitors in which the 1,4-diazepane moiety was designed to interact with the S4 aryl-binding domain of the fXa active site. Compound 13 (YM-96765) showed potent fXa inhibitory activity (IC50 = 6.8 nM) and effective antithrombotic activity without prolonging bleeding time. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.022