tert-butyl 4-(4-{[(7-cyano-2-napthyl)methyl][(2-ethoxy-2-oxoethyl)sulfonyl]amino}phenyl)-1,4-diazepane-1-carboxylate | 286430-88-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl 4-(4-{[(7-cyano-2-napthyl)methyl][(2-ethoxy-2-oxoethyl)sulfonyl]amino}phenyl)-1,4-diazepane-1-carboxylate
• 英文别名: ethyl [N-[4-(4-t-butoxycarbonylhexa-hydro-1H-1,4-diazepin-1-yl)phenyl]-N-[(7-cyano-2-naphthyl)methyl]sulfamoyl]acetate；Tert-butyl 4-[4-[(7-cyanonaphthalen-2-yl)methyl-(2-ethoxy-2-oxoethyl)sulfonylamino]phenyl]-1,4-diazepane-1-carboxylate
• CAS: 286430-88-4
• 化学式: C₃₂H₃₈N₄O₆S
• 分子量: 606.743
• InChiKey: QXBUSIDZVUBGKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(4-{[(7-cyano-2-napthyl)methyl][(2-ethoxy-2-oxoethyl)sulfonyl]amino}phenyl)-1,4-diazepane-1-carboxylate 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 5.0h， 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
• 作为产物：
  描述：

  tert-butyl 4-(4-aminophenyl)-1,4-diazepane-1-carboxylate 在 吡啶 、 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 17.0h， 生成 tert-butyl 4-(4-{[(7-cyano-2-napthyl)methyl][(2-ethoxy-2-oxoethyl)sulfonyl]amino}phenyl)-1,4-diazepane-1-carboxylate
  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

• Hexahydro-1,4-diazepine derivatives or salts thereof
  申请人：Yamanouchi Pharmaceutical Co.

  公开号：US06333320B1

  公开（公告）日：2001-12-25

  Hexahydro-1,4-diazepine derivatives represented by general formula (I); pharmaceutically acceptable salts thereof; and drugs containing the same as the active ingredient, such as activated blood coagulation factor X inhibitor, wherein A: phenylene, pyridylene, or the like; B: a 5- or 6-membered aryl or heteroaryl ring; X: —CO—, —CONH—, —CSNH—, —SO2—, —SO2NH—, or the like; Y: a bond or alkylene; R1: hydrogen, alkyl, —Y—(hetero) aryl, or the like; R2: hydrogen, alkoxy, —COOH, or the like; R3: amidino or a group capable of being converted into amidino; and R4, R5: each independently hydrogen or lower alkyl.

  一般式（I）所代表的六氢-1,4-二氮杂环衍生物；其药学上可接受的盐；以及包含其作为活性成分的药物，例如激活的血凝血因子X抑制剂，其中A：苯撑基，吡啶撑基或类似物；B：5-或6-成员芳基或杂芳基环；X：-CO-，-CONH-，-CSNH-，-SO2-，-SO2NH-或类似物；Y：键或烷基；R1：氢，烷基，-Y-（杂）芳基或类似物；R2：氢，烷氧基，-COOH或类似物；R3：酰胺基或可转化为酰胺基的基团；以及R4，R5：各自独立地为氢或低级烷基。