ethyl 3-amino-4-[(3-cyanophenylamino)methyl]benzoate | 365462-70-0

• 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: ethyl 3-amino-4-[(3-cyanophenylamino)methyl]benzoate
• 英文别名: ethyl 3-amino-4-[(3-cyanoanilino)methyl]benzoate
• CAS: 365462-70-0
• 化学式: C₁₇H₁₇N₃O₂
• 分子量: 295.341
• InChiKey: RRXXTIUAPDDLHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-4-[(3-cyanophenylamino)methyl]benzoate 在 吡啶 、 乙酸铵 、 盐酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 80.0h， 生成 ethyl 4-[({3-[amino(imino)methyl]phenyl}amino)methyl]-3-{[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}benzoate
  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：

  乙基 4-甲基-3-硝基苯甲酸 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 ammonium chloride 、 铁粉 、 potassium carbonate 作用下， 以 四氯化碳 、 乙醇 、 水 、 乙腈 为溶剂， 反应 27.5h， 生成 ethyl 3-amino-4-[(3-cyanophenylamino)methyl]benzoate
  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

• Diazepane derivatives or salts thereof
  申请人：——

  公开号：US20030195193A1

  公开（公告）日：2003-10-16

  To provide a compound which has an anticoagulation action based upon inhibition of activated blood coagulation factor X and is useful as an anticoagulant or an agent for prevention and treatment of diseases caused by thrombus or embolus. A diazepan derivative such as 4-[(3-carbamimidoylphenylamino)methyl]-3-[4-(4-methyl-1,4-diazepan-1-yl)benzoylamino]benzoic acid and 3-hydroxy-4′methoxy-2-{[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}benzanilide or a salt thereof is an effective ingredient.

  提供一种基于抑制活化的血液凝血因子X而具有抗凝作用的化合物，可用作抗凝剂或预防和治疗由血栓或栓塞引起的疾病的药物。4-[(3-羧基胍基苯基氨基)甲基]-3-[4-(4-甲基-1,4-二氮杂环庚烷-1-基)苯甲酰氨基]苯甲酸和3-羟基-4′-甲氧基-2-{[4-(4-甲基-1,4-二氮杂环庚烷-1-基)苯甲酰]氨基}苯甲酰胺或其盐是有效成分。
• Diazepan derivatives or salts thereof
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：US20040068109A1

  公开（公告）日：2004-04-08

  To provide a compound which has an anticoagulation action based upon inhibition of activated blood coagulation factor X and is useful as an anticoagulant or an agent for prevention and treatment of diseases caused by thrombus or embolus. A diazepan derivative such as 4-[(3-carbamimidoylphenylamino)methyl]-3-[4-(4-methyl-1,4-diazepan-1-yl)benzoylamino]benzoic acid and 3-hydroxy-4′-methoxy-2-{[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}benzanilide or a salt thereof is an effective ingredient.

  提供一种化合物，其基于抑制活化的血液凝血因子X具有抗凝作用，并可用作抗凝剂或预防和治疗由血栓或栓子引起的疾病的药物。一种苯二氮平衍生物，例如4-[(3-氨基甲酰苯基)氨基甲基]-3-[(4-甲基-1,4-二氮平-1-基)苯甲酰氨基]苯甲酸和3-羟基-4'-甲氧基-2-[4-(4-甲基-1,4-二氮平-1-基)苯甲酰]氨基}苯甲酰苯胺或其盐是有效成分。
• DIAZEPANE DERIVATIVES OR SALTS THEREOF
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP1273575A1

  公开（公告）日：2003-01-08

  To provide a compound which has an anticoagulation action based upon inhibition of activated blood coagulation factor X and is useful as an anticoagulant or an agent for prevention and treatment of diseases caused by thrombus or embolus. A diazepan derivative such as 4-[(3-carbamimidoylphenylamino)methyl]-3-[4-(4-methyl-1,4-diazepan-1-yl)benzoylamino]benzoic acid and 3-hydroxy-4'-methoxy-2-[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}benzanilide or a salt thereof is an effective ingredient.

  提供一种化合物，它具有基于抑制活化的血液凝固因子 X 的抗凝作用，可用作抗凝剂或预防和治疗由血栓或栓子引起的疾病的药物。一种二氮杂卓衍生物，如 4-[(3-氨基甲酰基苯基氨基)甲基]-3-[4-(4-甲基-1,4-二氮杂卓-1-基)苯甲酰基氨基]苯甲酸和 3-羟基-4'-甲氧基-2-[4-(4-甲基-1,4-二氮杂卓-1-基)苯甲酰基]氨基}苯甲酰苯胺或其盐是一种有效成分。
• Diazepan derivatives useful as factor X inhibitor
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP1415990A1

  公开（公告）日：2004-05-06

  To provide a compound which has an anticoagulation action based upon inhibition of activated blood coagulation factor X and is useful as an anticoagulant or an agent for prevention and treatment of diseases caused by thrombus or embolus. A diazepan derivative such as 4-[(3-carbamimidoylphenylamino)methyl]-3-[4-(4-methyl-1,4-diazepan-1-yl)benzoylamino]benzoic acid and 3-hydroxy-4'-methoxy-2-[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}benzanilide or a salt thereof is an effective ingredient.

  提供一种化合物，它具有基于抑制活化的血液凝固因子 X 的抗凝作用，可用作抗凝剂或预防和治疗由血栓或栓子引起的疾病的药物。一种二氮杂卓衍生物，如 4-[(3-氨基甲酰基苯基氨基)甲基]-3-[4-(4-甲基-1,4-二氮杂卓-1-基)苯甲酰基氨基]苯甲酸和 3-羟基-4'-甲氧基-2-[4-(4-甲基-1,4-二氮杂卓-1-基)苯甲酰基]氨基}苯甲酰苯胺或其盐是一种有效成分。
• USRE043481E1
  申请人：——

  公开号：——

  公开（公告）日：——