ethyl ({({7-[amino(imino)methyl]-2-naphthyl}methyl)[4-(4-ethanimidoyl-1,4-diazepan-1-yl)phenyl]amino}sulfonyl)acetate | 220220-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl ({({7-[amino(imino)methyl]-2-naphthyl}methyl)[4-(4-ethanimidoyl-1,4-diazepan-1-yl)phenyl]amino}sulfonyl)acetate
• 英文别名: Ethyl [N-[4-(4-acetimidoylhexahydro-1H-1,4-diazepin-1-yl) phenyl]-N-[(7-amidino-2-naphthyl)methyl]-sulfamoyl]acetate；Ethyl 2-[(7-carbamimidoylnaphthalen-2-yl)methyl-[4-(4-ethanimidoyl-1,4-diazepan-1-yl)phenyl]sulfamoyl]acetate；ethyl 2-[(7-carbamimidoylnaphthalen-2-yl)methyl-[4-(4-ethanimidoyl-1,4-diazepan-1-yl)phenyl]sulfamoyl]acetate
• CAS: 220220-41-7
• 化学式: C₂₉H₃₆N₆O₄S
• 分子量: 564.709
• InChiKey: AFVSBRGUQJCVCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  152
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl ({({7-[amino(imino)methyl]-2-naphthyl}methyl)[4-(4-ethanimidoyl-1,4-diazepan-1-yl)phenyl]amino}sulfonyl)acetate 在 盐酸 作用下， 反应 15.0h， 以62%的产率得到[N-[4-(4-acet-imidoylhexahydro-1H-1,4-diazepin-1-yl)phenyl]-N-[(7-amidino-2-naphthyl)methyl]sulfamoyl]acetic acid dihydro-chloride
  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
• 作为产物：
  描述：

  1,4-二氮杂环庚烷-1-甲酸叔丁酯 在 palladium on activated charcoal 吡啶 、 盐酸 、 乙醇 、 氢气 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 109.0h， 生成 ethyl ({({7-[amino(imino)methyl]-2-naphthyl}methyl)[4-(4-ethanimidoyl-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

文献信息

• Synthesis and biological activity of novel 1,4-diazepane derivatives as factor Xa inhibitor with potent anticoagulant and antithrombotic activity
  作者：Hiroyuki Koshio、Fukushi Hirayama、Tsukasa Ishihara、Yuta Taniuchi、Kazuo Sato、Yumiko Sakai-Moritani、Seiji Kaku、Tomihisa Kawasaki、Yuzo Matsumoto、Shuichi Sakamoto、Shin-ichi Tsukamoto

  DOI：10.1016/j.bmc.2004.02.022

  日期：2004.5

  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.