3-[(2-nitrobenzyl)amino]benzonitrile | 840531-00-2

• 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: 3-[(2-nitrobenzyl)amino]benzonitrile
• 英文别名: 3-[(2-Nitrophenyl)methylamino]benzonitrile
• CAS: 840531-00-2
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: YNXMVOSQQCPDQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  81.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(2-nitrobenzyl)amino]benzonitrile 在 吡啶 、 ammonium chloride 、 铁粉 作用下， 以 乙醇 、 水 为溶剂， 反应 20.5h， 生成 N-(2-{[(3-cyanophenyl)amino]methyl}phenyl)-4-(4-methyl-1,4-diazepan-1-yl)benzamide
  参考文献：
  名称：

  Synthesis and biological activity of novel 1,2-disubstituted benzene derivatives as factor Xa inhibitors

  摘要：

  Factor Xa (fXa) is a serine protease that plays a pivotal role in the coagulation cascade. High-tbroughput screening of the Yamanouchi compound library yielded lead compound I with the ability to inhibit fXa at micromolar concentrations. To improve its fXa inhibitory activity and its oral anticoagulant activity, the linker between benzamidine and the central benzene ring was modified and a carboxyl group was introduced at the central benzene ring. The resulting compounds 40b (YM-203552), 41a (YM-202054), and 41c (YM-203558) exhibited potent fXa inhibitory activity and oral anticoagulant activity. In particular, YM-203558 exhibited the most potent oral anticoagulant activity, prolonging PT more than 3-fold at 0.5 and 2.0h. Additionally, these compounds showed a high degree of selectivity for other serine proteases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.005
• 作为产物：
  描述：

  间氨基苯甲腈 、 邻硝基苯甲醛 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 19.0h， 以89%的产率得到3-[(2-nitrobenzyl)amino]benzonitrile
  参考文献：
  名称：

  Synthesis and biological activity of novel 1,2-disubstituted benzene derivatives as factor Xa inhibitors

  摘要：

  Factor Xa (fXa) is a serine protease that plays a pivotal role in the coagulation cascade. High-tbroughput screening of the Yamanouchi compound library yielded lead compound I with the ability to inhibit fXa at micromolar concentrations. To improve its fXa inhibitory activity and its oral anticoagulant activity, the linker between benzamidine and the central benzene ring was modified and a carboxyl group was introduced at the central benzene ring. The resulting compounds 40b (YM-203552), 41a (YM-202054), and 41c (YM-203558) exhibited potent fXa inhibitory activity and oral anticoagulant activity. In particular, YM-203558 exhibited the most potent oral anticoagulant activity, prolonging PT more than 3-fold at 0.5 and 2.0h. Additionally, these compounds showed a high degree of selectivity for other serine proteases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.005

文献信息

• Synthesis and biological activity of novel 1,2-disubstituted benzene derivatives as factor Xa inhibitors
  作者：Hiroyuki Koshio、Fukushi Hirayama、Tsukasa Ishihara、Ryouta Shiraki、Takeshi Shigenaga、Yuta Taniuchi、Kazuo Sato、Yumiko Moritani、Yoshiyuki Iwatsuki、Seiji Kaku、Naoko Katayama、Tomihisa Kawasaki、Yuzo Matsumoto、Shuichi Sakamoto、Shin-ichi Tsukamoto

  DOI：10.1016/j.bmc.2004.11.005

  日期：2005.2

  Factor Xa (fXa) is a serine protease that plays a pivotal role in the coagulation cascade. High-tbroughput screening of the Yamanouchi compound library yielded lead compound I with the ability to inhibit fXa at micromolar concentrations. To improve its fXa inhibitory activity and its oral anticoagulant activity, the linker between benzamidine and the central benzene ring was modified and a carboxyl group was introduced at the central benzene ring. The resulting compounds 40b (YM-203552), 41a (YM-202054), and 41c (YM-203558) exhibited potent fXa inhibitory activity and oral anticoagulant activity. In particular, YM-203558 exhibited the most potent oral anticoagulant activity, prolonging PT more than 3-fold at 0.5 and 2.0h. Additionally, these compounds showed a high degree of selectivity for other serine proteases. (C) 2004 Elsevier Ltd. All rights reserved.