Ethanone, 1-[2-(cyclohexylamino)-5-nitrophenyl]- | 1187396-05-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethanone, 1-[2-(cyclohexylamino)-5-nitrophenyl]-
• 英文别名: 1-[2-(cyclohexylamino)-5-nitrophenyl]ethanone
• CAS: 1187396-05-9
• 化学式: C₃₀H₄₀N₅O₅Pol
• 分子量: 262.3
• InChiKey: PROQTAWYXBIJLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethanone, 1-[2-(cyclohexylamino)-5-nitrophenyl]- 生成
  参考文献：
  名称：

  Therapeutic Index of Gramicidin S is Strongly Modulated by d-Phenylalanine Analogues at the β-Turn

  摘要：

  Analogues of the cationic antimicrobial peptide gramicidin S (GS), cyclo(Val-Orn-Leu-D-Phe-Pro)(2), with D-Phe residues replaced by different (restricted mobility, mostly) surrogates have been synthesized and used in SAR studies against several pathogenic bacteria. While all D-Phe substitutions are shown by NMR to preserve the overall beta-sheet conformation, they entail subtle structural alterations that lead to significant modifications in biological activity. In particular, the analogue incorporating D-Tic (1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) shows a modest but significant increase in therapeutic index, mostly due to a sharp decrease in hemolytic effect. The fact that NMR data show a shortened distance between the D-Tic aromatic ring and the Orn delta-amino group may help explain the improved antibiotic profile of this analogue.

  DOI：

  10.1021/jm800886n
• 作为产物：
  描述：

  生成 Ethanone, 1-[2-(cyclohexylamino)-5-nitrophenyl]-
  参考文献：
  名称：

  Therapeutic Index of Gramicidin S is Strongly Modulated by d-Phenylalanine Analogues at the β-Turn

  摘要：

  Analogues of the cationic antimicrobial peptide gramicidin S (GS), cyclo(Val-Orn-Leu-D-Phe-Pro)(2), with D-Phe residues replaced by different (restricted mobility, mostly) surrogates have been synthesized and used in SAR studies against several pathogenic bacteria. While all D-Phe substitutions are shown by NMR to preserve the overall beta-sheet conformation, they entail subtle structural alterations that lead to significant modifications in biological activity. In particular, the analogue incorporating D-Tic (1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) shows a modest but significant increase in therapeutic index, mostly due to a sharp decrease in hemolytic effect. The fact that NMR data show a shortened distance between the D-Tic aromatic ring and the Orn delta-amino group may help explain the improved antibiotic profile of this analogue.

  DOI：

  10.1021/jm800886n

文献信息

• Preparation of 5-nitro-2-amino[<i>b</i>]thiophenes and 1-(2-amino-5-nitrophenyl)ethanones<i>via</i>microwave irradiation
  作者：Afsha Rais、Haribabu Ankati、Ed Biehl

  DOI：10.1002/jhet.88

  日期：2009.7

  1-(2-Chloro-5-nitrophenyl)ethanone) reacts with various amines in the presence of sulfur under microwave radiation to give the corresponding 2-aminobenzo[b]-thiophenes in good yields. The yields of are vastly superior to those obtained using conventional heating. Additionally, 1-(2-amino-5-nitrophenyl)ethanones were also obtained. A mechanism is proposed in which 2-amino thiophenes are formed by a

  1-（2-氯-5-硝基苯基）乙酮在微波辐射下在硫的存在下与各种胺反应，生成相应的2-氨基苯并[ b ]-噻吩丰产。的产量大大优于使用常规加热获得的那些。此外，1-（2-氨基-5-硝基苯基）乙酮也获得了。提出了一种机制，其中2-氨基噻吩由S被形成Ñ氩机制涉及分子内加成中间硫代酰胺的硫与2-取代碳，得到迈森海梅复合物，其折叠到2-氨基噻吩和2-氨基酮（）是由涉及亲核加成胺的2-氯位置的平行途径形成的形成Meisensheimer配合物，该配合物崩解为氨基乙酮。J.杂环化​​学，（2009）。
• Therapeutic Index of Gramicidin S is Strongly Modulated by <scp>d</scp>-Phenylalanine Analogues at the β-Turn
  作者：Concepción Solanas、Beatriz G. de la Torre、María Fernández-Reyes、Clara M. Santiveri、M. Ángeles Jiménez、Luis Rivas、Ana I. Jiménez、David Andreu、Carlos Cativiela

  DOI：10.1021/jm800886n

  日期：2009.2.12

  Analogues of the cationic antimicrobial peptide gramicidin S (GS), cyclo(Val-Orn-Leu-D-Phe-Pro)(2), with D-Phe residues replaced by different (restricted mobility, mostly) surrogates have been synthesized and used in SAR studies against several pathogenic bacteria. While all D-Phe substitutions are shown by NMR to preserve the overall beta-sheet conformation, they entail subtle structural alterations that lead to significant modifications in biological activity. In particular, the analogue incorporating D-Tic (1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) shows a modest but significant increase in therapeutic index, mostly due to a sharp decrease in hemolytic effect. The fact that NMR data show a shortened distance between the D-Tic aromatic ring and the Orn delta-amino group may help explain the improved antibiotic profile of this analogue.