ethyl 4-benzamido-1-methylimidazole-2-carboxylate | 1359164-22-9

• 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 4-benzamido-1-methylimidazole-2-carboxylate
• CAS: 1359164-22-9
• 化学式: C₁₄H₁₅N₃O₃
• 分子量: 273.291
• InChiKey: VYEODMAFXCDKMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-benzamido-1-methylimidazole-2-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.75h， 以85%的产率得到4-benzamido-1-methylimidazole-2-carboxylic acid
  参考文献：
  名称：

  Novel diamino imidazole and pyrrole-containing polyamides: Synthesis and DNA binding studies of mono- and diamino-phenyl-ImPy*Im polyamides designed to target 5′-ACGCGT-3′

  摘要：

  Pyrrole- and imidazole-containing polyamides are widely investigated as DNA sequence selective binding agents that have potential use as gene control agents. The key challenges that must be overcome to realize this goal is the development of polyamides with low molar mass so the molecules can readily diffuse into cells and concentrate in the nucleus. In addition, the molecules must have appreciable water solubility, bind DNA sequence specifically, and with high affinity. It is on this basis that the orthogonally positioned diamino/dicationic polyamide Ph-ImPy*Im 5 was designed to target the sequence 5'-ACGCGT-3'. Py* denotes the pyrrole unit that contains a N-substituted aminopropyl pendant group. The DNA binding properties of diamino polyamide 5 were determined using a number of techniques including CD, Delta T(M), DNase I footprinting, SPR and ITC studies. The effects of the second amino moiety in Py* on DNA binding affinity over its monoamino counterpart Ph-ImPylm 3 were assessed by conducting DNA binding studies of 3 in parallel with 5. The results confirmed the minor groove binding and selectivity of both polyamides for the cognate sequence 5'-ACGCGT-3'. The diamino/dicationic polyamide 5 showed enhanced binding affinity and higher solubility in aqueous media over its monoamino/monocationic counterpart Ph-ImPylm 3. The binding constant of 5, determined from SPR studies, was found to be 1.5 x 10(7) M(-1), which is similar to 3 times higher than that for its monoamino analog 3 (4.8 x 10(6) M(-1)). The affinity of 5 is now approaching that of the parent compound f-ImPyIm 1 and its diamino equivalent 4. The advantages of the design of diamino polyamide 5 over 1 and 4 are its sequence specificity and the ease of synthesis compared to the N-terminus pyrrole analog 2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.010
• 作为产物：
  描述：

  1-甲基-4-硝基咪唑-2-羧酸乙酯 在 5%-palladium/activated carbon 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 ethyl 4-benzamido-1-methylimidazole-2-carboxylate
  参考文献：
  名称：

  Novel diamino imidazole and pyrrole-containing polyamides: Synthesis and DNA binding studies of mono- and diamino-phenyl-ImPy*Im polyamides designed to target 5′-ACGCGT-3′

  摘要：

  Pyrrole- and imidazole-containing polyamides are widely investigated as DNA sequence selective binding agents that have potential use as gene control agents. The key challenges that must be overcome to realize this goal is the development of polyamides with low molar mass so the molecules can readily diffuse into cells and concentrate in the nucleus. In addition, the molecules must have appreciable water solubility, bind DNA sequence specifically, and with high affinity. It is on this basis that the orthogonally positioned diamino/dicationic polyamide Ph-ImPy*Im 5 was designed to target the sequence 5'-ACGCGT-3'. Py* denotes the pyrrole unit that contains a N-substituted aminopropyl pendant group. The DNA binding properties of diamino polyamide 5 were determined using a number of techniques including CD, Delta T(M), DNase I footprinting, SPR and ITC studies. The effects of the second amino moiety in Py* on DNA binding affinity over its monoamino counterpart Ph-ImPylm 3 were assessed by conducting DNA binding studies of 3 in parallel with 5. The results confirmed the minor groove binding and selectivity of both polyamides for the cognate sequence 5'-ACGCGT-3'. The diamino/dicationic polyamide 5 showed enhanced binding affinity and higher solubility in aqueous media over its monoamino/monocationic counterpart Ph-ImPylm 3. The binding constant of 5, determined from SPR studies, was found to be 1.5 x 10(7) M(-1), which is similar to 3 times higher than that for its monoamino analog 3 (4.8 x 10(6) M(-1)). The affinity of 5 is now approaching that of the parent compound f-ImPyIm 1 and its diamino equivalent 4. The advantages of the design of diamino polyamide 5 over 1 and 4 are its sequence specificity and the ease of synthesis compared to the N-terminus pyrrole analog 2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.010

文献信息

• Processes For Forming Amide Bonds And Compositions Related Thereto
  申请人：Liebeskind Lanny S.

  公开号：US20120107902A1

  公开（公告）日：2012-05-03

  The disclosure relates to methods for producing amide bonds and reagents related thereto. In some embodiments, the disclosure relates to methods of producing an amide comprising mixing an O-silylated thionoester and an amine under conditions such that an amide is formed. In another embodiment, the disclosure relates to mixing a thiolacid, a silylating agent, and an amine under conditions such that an amide is formed.

  本披露涉及生产酰胺键的方法及相关试剂。在某些实施例中，本披露涉及生产酰胺的方法，包括混合O-硅基硫代酯和胺，以形成酰胺。在另一实施例中，本披露涉及混合硫酸、硅基化试剂和胺的方法，以形成酰胺。
• PROCESSES FOR FORMING AMIDE BONDS AND COMPOSITIONS RELATED THERETO
  申请人：EMORY UNIVERSITY

  公开号：US20150315129A1

  公开（公告）日：2015-11-05

  The disclosure relates to methods for producing amide bonds and reagents related thereto. In some embodiments, the disclosure relates to methods of producing an amide comprising mixing an O-silylated thionoester and an amine under conditions such that an amide is formed. In another embodiment, the disclosure relates to mixing a thiolacid, a silylating agent, and an amine under conditions such that an amide is formed.

  本公开涉及制备酰胺键及其相关试剂的方法。在一些实施例中，本公开涉及制备酰胺的方法，包括混合O-硅基硫酰酯和胺，在形成酰胺的条件下进行。在另一实施例中，本公开涉及混合硫酸酯、硅基化试剂和胺，在形成酰胺的条件下进行。
• US8921599B2
  申请人：——

  公开号：US8921599B2

  公开（公告）日：2014-12-30
• US9382193B2
  申请人：——

  公开号：US9382193B2

  公开（公告）日：2016-07-05