2-amino-4-(3-heptanoylamino-propyl)imidazole-1-carboxylic acid tert-butyl ester | 1110786-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-amino-4-(3-heptanoylamino-propyl)imidazole-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 2-amino-4-[3-(heptanoylamino)propyl]imidazole-1-carboxylate；tert-butyl 2-amino-4-[3-(heptanoylamino)propyl]imidazole-1-carboxylate
• CAS: 1110786-22-5
• 化学式: C₁₈H₃₂N₄O₃
• 分子量: 352.477
• InChiKey: NBSWBAPROHMRJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  99.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-4-(3-heptanoylamino-propyl)imidazole-1-carboxylic acid tert-butyl ester 在 三氟乙酸 、 盐酸 作用下， 以 二氯甲烷 、 乙醚 为溶剂， 反应 12.0h， 以99%的产率得到heptanoic acid [3-(2-amino-1H-imidazol-4-yl)propyl]amide hydrochloride
  参考文献：
  名称：

  Antibiofilm Activity of a Diverse Oroidin Library Generated through Reductive Acylation

  摘要：

  A diverse 20-compound library of analogues based on the marine alkaloid oroidin were synthesized via a reductive acylation strategy. The final target was then assayed for inhibition and dispersion activity against common proteo-bacteria known to form biofilms. This methodology represents a significant improvement over the generality of known methods to acylate substrates containing 2-aminoimidazoles and has the potential to have broad application to the synthesis of more advanced oroidin family members and their corresponding analogues.

  DOI：

  10.1021/jo802260t
• 作为产物：
  描述：

  tert-butyl 2-amino-4-(3-aminopropyl)-1H-imidazole-1-carboxylate 、 庚酰氯 以 四氢呋喃 、 二氯甲烷 为溶剂， 以0.096 g的产率得到2-amino-4-(3-heptanoylamino-propyl)imidazole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Antibiofilm Activity of a Diverse Oroidin Library Generated through Reductive Acylation

  摘要：

  A diverse 20-compound library of analogues based on the marine alkaloid oroidin were synthesized via a reductive acylation strategy. The final target was then assayed for inhibition and dispersion activity against common proteo-bacteria known to form biofilms. This methodology represents a significant improvement over the generality of known methods to acylate substrates containing 2-aminoimidazoles and has the potential to have broad application to the synthesis of more advanced oroidin family members and their corresponding analogues.

  DOI：

  10.1021/jo802260t

文献信息

• Synthesis and Antibiofilm Activity of a Second-Generation Reverse-Amide Oroidin Library: A Structure-Activity Relationship Study
  作者：T. Eric Ballard、Justin J. Richards、Amanda L. Wolfe、Christian Melander

  DOI：10.1002/chem.200801419

  日期：——

  A second-generation library of 2-aminoimidazole-based derivatives incorporating a "reversed amide" (RA) motif in comparison to the marine natural product oroidin were synthesized and subsequently assayed for antibiofilm activity against the medically relevant Gram-negative proteobacteria P. aeruginosa and A. baumannii. Most notably, an in-depth activity profile is reported for the most active subclass

  合成了第二代基于2-氨基咪唑的衍生物，与海洋天然产物oroidin相比，该衍生物结合了“反向酰胺”（RA）主题，随后针对医学上相关的革兰氏阴性菌铜绿假单胞菌和铜绿假单胞菌鲍曼不动杆菌 最值得注意的是，据报道，活性最高的衍生物亚类具有更深的活性，这些亚类的酰胺键上带有线性脂族链。另外，核心模板的进一步结构修饰，例如酰胺键的去除或三唑等排物的取代，导致发现了具有抗生物膜活性的类似物，其对铜绿假单胞菌和铜绿假单胞菌的抑制和分散特性各不相同。鲍曼生物膜。
• Antibiofilm Activity of a Diverse Oroidin Library Generated through Reductive Acylation
  作者：T. Eric Ballard、Justin J. Richards、Arianexys Aquino、Catherine S. Reed、Christian Melander

  DOI：10.1021/jo802260t

  日期：2009.2.20

  A diverse 20-compound library of analogues based on the marine alkaloid oroidin were synthesized via a reductive acylation strategy. The final target was then assayed for inhibition and dispersion activity against common proteo-bacteria known to form biofilms. This methodology represents a significant improvement over the generality of known methods to acylate substrates containing 2-aminoimidazoles and has the potential to have broad application to the synthesis of more advanced oroidin family members and their corresponding analogues.