tert-butyl 4-(2-(1H-imidazol-1-yl)acetyl)piperazine-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: tert-butyl 4-(2-(1H-imidazol-1-yl)acetyl)piperazine-1-carboxylate
• 英文别名: Tert-butyl 4-(2-imidazol-1-ylacetyl)piperazine-1-carboxylate
• 化学式: C₁₄H₂₂N₄O₃
• 分子量: 294.354
• InChiKey: VAOGEFIMFWBYRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(2-(1H-imidazol-1-yl)acetyl)piperazine-1-carboxylate 、 三氟乙酸 以 氯仿 为溶剂， 以61%的产率得到4-(2-(1H-imidazole-1-yl)acetyl)piperazin-1-ium trifluoroacetate
  参考文献：
  名称：

  Synthesis of a 4-nitroimidazole indocyanine dye-conjugate and imaging of tumor hypoxia in BALB/c tumor-bearing female mice

  摘要：

  Extending our previous work with 2-nitroimidazole-indocyanine dye-conjugate 4, we prepared the 4-nitroimidazole-piperazine-indocyanine derivative (6). We also prepared imidazole derivative 5 as a control. We compared the in vivo hypoxia targeting performance of both 5 and 6 with the previously tested 4, and 6 showed a higher fluorescent intensity after 15 min post-injection, about 1.5-fold higher than 4 and 2.5-fold higher than 5. Cells treated with 6 under hypoxic conditions showed a higher fluorescence yield when compared to the cells kept under normoxic conditions. All findings were supported with fluorescence images of histological sections of tumor samples using a Li-COR scanner and an immunohistochemistry technique for tumor hypoxia. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.12.010
• 作为产物：
  描述：

  咪唑 、 4-(2-溴乙酰基)哌嗪-1-羧酸叔丁酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以67%的产率得到tert-butyl 4-(2-(1H-imidazol-1-yl)acetyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Synthesis of a 4-nitroimidazole indocyanine dye-conjugate and imaging of tumor hypoxia in BALB/c tumor-bearing female mice

  摘要：

  Extending our previous work with 2-nitroimidazole-indocyanine dye-conjugate 4, we prepared the 4-nitroimidazole-piperazine-indocyanine derivative (6). We also prepared imidazole derivative 5 as a control. We compared the in vivo hypoxia targeting performance of both 5 and 6 with the previously tested 4, and 6 showed a higher fluorescent intensity after 15 min post-injection, about 1.5-fold higher than 4 and 2.5-fold higher than 5. Cells treated with 6 under hypoxic conditions showed a higher fluorescence yield when compared to the cells kept under normoxic conditions. All findings were supported with fluorescence images of histological sections of tumor samples using a Li-COR scanner and an immunohistochemistry technique for tumor hypoxia. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.12.010

文献信息

• Serine protease inhibitors
  申请人：——

  公开号：US20030055246A1

  公开（公告）日：2003-03-20

  The invention relates to serine protease inhibitor compounds of formula (I) where R 1 is hydrogen, halo, cyano, nitro or hydroxyl, amino, alkoxy, alkyl, aminoalkyl, hydroxyalkyl, thiol, alkylthio, aminosulphonyl, alkoxyalkyl, alkoxycarbonyl, acyloxymethoxycarbonyl or alkylamino optionally substituted by hydroxy, alkylamino, alkoxy, oxo, aryl, cycloalkyl, amino, halo, cyano, nitro, thiol, alkylthio, alkylsulphonyl, alkylsulphenyl, alkylsulphonamido, alkylaminosulphonyl, haloalkoxy and haloalkyl; R 2 is hydrogen, halo, methyl, amino, hydroxy, or oxo; and R is X—X—Y(R 7 )—L—Lp(D)n; wherein each X independently is a C, N, O or S atom or a CO, CR 1 , C(R 1 ) 2 or NR 1 group, at least one X being C, CO, CR 1 or a C(R 1 ) 2 group; Y (the &agr;-atom) is a nitrogen atom or a CR 1 group or Y and L taken together form a cyclic group; R 7 is a lipophilic group selected from alkyl, alkenyl, mono- or bi-cycloalkyl, aryl, heteroaryl, mono- or bicycloalkylalkyl, mono- or bicycloalkylalkenyl, aralkyl, heteroaryl-alkyl, arylalkenyl, heteroarylalkenyl all optionally substituted by a group R 1 ; L is an organic linker group containing 1 to 5 backbone atoms selected from C, N, O and S, or a branched alkyl or cyclic group; Lp is a lipophilic organic group selected from alkyl, heterocyclic, alkenyl, alkaryl, cycloalkyl, polycycloalkyl, cycloalkenyl, aryl, aralkyl or haloalkyl group or a combination of two or more such groups optionally substituted by one or more of oxa, thia, aza or R 1 groups; D is a hydrogen bond donor group; and n is 0, 1 or 2 and salts thereof.

  本发明涉及公式（I）的丝氨酸蛋白酶抑制剂化合物，其中R1为氢、卤素、氰基、硝基或羟基、氨基、烷氧基、烷基、氨基烷基、羟基烷基、硫醇基、烷硫基、氨基磺酰基、烷氧基烷基、烷氧羰基、酰氧甲氧羰基或烷基氨基，可选择地被羟基、烷基氨基、烷氧基、氧代、芳基、环烷基、氨基、卤素、氰基、硝基、硫醇基、烷硫基、烷基磺酰基、烷基磺酚基、烷基磺酰胺基、烷基氨基磺酰基、卤代烷氧基和卤代烷基取代；R2为氢、卤素、甲基、氨基、羟基或氧代；R为X—X—Y（R7）—L—Lp（D）n；其中每个X独立地为C、N、O或S原子或CO、CR1、C（R1）2或NR1基团，至少一个X为C、CO、CR1或C（R1）2基团；Y（α原子）为氮原子或CR1基团，或Y和L共同形成一个环状基团；R7为从烷基、烯基、单环或双环烷基、芳基、杂芳基、单环或双环烷基烷基、单环或双环烷基烯基、芳基烷基、杂芳基烷基、芳基烯基、杂芳基烯基中选择的亲脂性基团，所有这些基团都可以选择地被R1基团取代；L为含有1至5个骨架原子的有机连接基团，所述骨架原子选择自C、N、O和S，或者是支链烷基或环状基团；Lp为从烷基、杂环、烯基、烷芳基、环烷基、多环烷基、环烯基、芳基、芳基烷基或卤代烷基中选择的亲脂性有机基团，或者是两个或更多这样的基团的组合，可选择地被氧代、硫代、氮代或R1基团取代；D为氢键供体基团；n为0、1或2及其盐。
• SERINE PROTEASE INHIBITORS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1289972A1

  公开（公告）日：2003-03-12
• EP1510515A1
  申请人：——

  公开号：EP1510515A1

  公开（公告）日：2005-03-02
• US6936611B2
  申请人：——

  公开号：US6936611B2

  公开（公告）日：2005-08-30
• US6946467B2
  申请人：——

  公开号：US6946467B2

  公开（公告）日：2005-09-20