4-(3-氨基-4-硝基苯基)-1-哌嗪乙酸乙酯 | 188247-41-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 4-(3-氨基-4-硝基苯基)-1-哌嗪乙酸乙酯
• 英文名称: ethyl 4-(3-amino-4-nitrophenyl)piperazinecarboxylate
• 英文别名: 4-(3'-amino-4'-nitrophenyl)piperazin-1-ylacetic acid ethyl ester；4-(3-Amino-4-nitrophenyl)-1-piperazineacetic acid ethyl ester；ethyl 2-[4-(3-amino-4-nitrophenyl)piperazin-1-yl]acetate
• CAS: 188247-41-8
• 化学式: C₁₄H₂₀N₄O₄
• 分子量: 308.337
• InChiKey: IOVLRVUFABZVBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(3-氨基-4-硝基苯基)-1-哌嗪乙酸乙酯 在 palladium on activated charcoal 氢溴酸 、 氢气 作用下， 以 水 、 乙酸乙酯 、 硝基苯 为溶剂， 反应 21.0h， 生成 {4-[2'-(4-Hydroxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-5-yl]-piperazin-1-yl}-acetic acid
  参考文献：
  名称：

  Molecular Recognition of DNA by Hoechst Benzimidazoles: Exploring Beyond the Pyrrole-Imidazole-Hydroxypyrrole Polyamide-Pairing Code

  摘要：

  A series of three-ring analogs of the minor-groove-binding molecule Hoechst 33258 (1), consisting of benzimidazole (B), imidazopyridine (P), and hydroxybenzimidazole (H) monomers, have been synthesized in order to investigate both their sequence specificity and binding modes. MPE.Fe-II Footprinting has revealed the preference of both PBB and BBB ligands for 5'-WGWWW-3' and 5'-WCWWW-3' tracts, as well as A T-rich sequences. Affinity-cleavage titrations show no evidence for a 2:1 binding mode of these Hoechst analogs. Importantly, all derivatives are oriented in one direction at each of their binding sites. The implications of these results for the design of minor-groove-binding small molecules is discussed.

  DOI：

  10.1002/1522-2675(20000906)83:9<2197::aid-hlca2197>3.0.co;2-n
• 作为产物：
  描述：

  2-硝基-5-氯苯胺 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 4-(3-氨基-4-硝基苯基)-1-哌嗪乙酸乙酯
  参考文献：
  名称：

  Molecular Recognition of DNA by Hoechst Benzimidazoles: Exploring Beyond the Pyrrole-Imidazole-Hydroxypyrrole Polyamide-Pairing Code

  摘要：

  A series of three-ring analogs of the minor-groove-binding molecule Hoechst 33258 (1), consisting of benzimidazole (B), imidazopyridine (P), and hydroxybenzimidazole (H) monomers, have been synthesized in order to investigate both their sequence specificity and binding modes. MPE.Fe-II Footprinting has revealed the preference of both PBB and BBB ligands for 5'-WGWWW-3' and 5'-WCWWW-3' tracts, as well as A T-rich sequences. Affinity-cleavage titrations show no evidence for a 2:1 binding mode of these Hoechst analogs. Importantly, all derivatives are oriented in one direction at each of their binding sites. The implications of these results for the design of minor-groove-binding small molecules is discussed.

  DOI：

  10.1002/1522-2675(20000906)83:9<2197::aid-hlca2197>3.0.co;2-n

文献信息

• 吡咯类BET降解剂及其应用
  申请人：中国药科大学

  公开号：CN114044768B

  公开（公告）日：2023-08-22

  本发明公开了一种吡咯类BET降解剂及其应用，属于生物医药技术领域。本发明采用PROTAC技术，提供了一类全新母核结构的BET蛋白降解剂，包括蛋白靶头A、连接子B、E3泛素化连接酶配体C。该BET蛋白降解剂具有优异蛋白抑制活性和抗肿瘤细胞增殖活性，与原蛋白靶头化合物相比，细胞活性具有大幅度提升；且制备方法路线较短，原料廉价易得。
• Radioprotectors
  申请人：Peter MacCallum Cancer Institute

  公开号：EP2044938B1

  公开（公告）日：2015-02-18
• Molecular Recognition of DNA by Hoechst Benzimidazoles: Exploring Beyond the Pyrrole-Imidazole-Hydroxypyrrole Polyamide-Pairing Code
  作者：Thomas G. Minehan、Konstanze Gottwald、Peter B. Dervan

  DOI：10.1002/1522-2675(20000906)83:9<2197::aid-hlca2197>3.0.co;2-n

  日期：2000.9.6

  A series of three-ring analogs of the minor-groove-binding molecule Hoechst 33258 (1), consisting of benzimidazole (B), imidazopyridine (P), and hydroxybenzimidazole (H) monomers, have been synthesized in order to investigate both their sequence specificity and binding modes. MPE.Fe-II Footprinting has revealed the preference of both PBB and BBB ligands for 5'-WGWWW-3' and 5'-WCWWW-3' tracts, as well as A T-rich sequences. Affinity-cleavage titrations show no evidence for a 2:1 binding mode of these Hoechst analogs. Importantly, all derivatives are oriented in one direction at each of their binding sites. The implications of these results for the design of minor-groove-binding small molecules is discussed.