methyl 3-([1,1'-biphenyl]-4-ylcarboxamido)-5-phenylthiophene-2-carboxylate | 477326-27-5

• 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: methyl 3-([1,1'-biphenyl]-4-ylcarboxamido)-5-phenylthiophene-2-carboxylate
• 英文别名: Methyl 5-phenyl-3-[(4-phenylbenzoyl)amino]thiophene-2-carboxylate
• CAS: 477326-27-5
• 化学式: C₂₅H₁₉NO₃S
• 分子量: 413.497
• InChiKey: OALPOVOHKRPTAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-([1,1'-biphenyl]-4-ylcarboxamido)-5-phenylthiophene-2-carboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 以81%的产率得到3-([1,1'-biphenyl]-4-ylcarboxamido)-5-phenylthiophene-2-carboxylic acid
  参考文献：
  名称：

  Benzamidobenzoic acids as potent PqsD inhibitors for the treatment of Pseudomonas aeruginosa infections

  摘要：

  Targeting PqsD is a promising novel approach to disrupt bacterial cell-to-cell-communication in Pseudomonas aeruginosa. In search of selective PqsD inhibitors, two series of benzamidobenzoic acids - one published as RNAP inhibitors and the other as PqsD inhibitors - were investigated for inhibitory activity toward the respective other enzyme. Additionally, novel derivatives were synthesized and biologically evaluated. By this means, the structural features needed for benzamidobenzoic acids to be potent and, most notably, selective PqsD inhibitors were identified. The most interesting compound of this study was the 3-Cl substituted compound 5 which strongly inhibits PqsD (IC50 6.2 mu M) while exhibiting no inhibition of RNAP. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.014
• 作为产物：
  描述：

  3-氨基-5-苯基-2-噻吩羧酸 在 4-二甲氨基吡啶 、 氯化亚砜 作用下， 反应 42.0h， 生成 methyl 3-([1,1'-biphenyl]-4-ylcarboxamido)-5-phenylthiophene-2-carboxylate
  参考文献：
  名称：

  Benzamidobenzoic acids as potent PqsD inhibitors for the treatment of Pseudomonas aeruginosa infections

  摘要：

  Targeting PqsD is a promising novel approach to disrupt bacterial cell-to-cell-communication in Pseudomonas aeruginosa. In search of selective PqsD inhibitors, two series of benzamidobenzoic acids - one published as RNAP inhibitors and the other as PqsD inhibitors - were investigated for inhibitory activity toward the respective other enzyme. Additionally, novel derivatives were synthesized and biologically evaluated. By this means, the structural features needed for benzamidobenzoic acids to be potent and, most notably, selective PqsD inhibitors were identified. The most interesting compound of this study was the 3-Cl substituted compound 5 which strongly inhibits PqsD (IC50 6.2 mu M) while exhibiting no inhibition of RNAP. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.014