(S)-3-(3-(1-carboxy-2-phenylethyl)ureido)thiophene-2-carboxylic acid

• 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
• 英文名称: (S)-3-(3-(1-carboxy-2-phenylethyl)ureido)thiophene-2-carboxylic acid
• 英文别名: 3-[[(1S)-1-carboxy-2-phenylethyl]carbamoylamino]thiophene-2-carboxylic acid
• 化学式: C₁₅H₁₄N₂O₅S
• 分子量: 334.353
• InChiKey: ZHZVVWVRNJTJSO-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-3-(3-(1-carboxy-2-phenylethyl)ureido)thiophene-2-carboxylic acid 在 盐酸 作用下， 反应 0.17h， 生成 (S)-5-benzyl-3-(thien-3-yl)imidazolidine-2,4-dione
  参考文献：
  名称：

  Efficient one-pot microwave-assisted synthesis of 3-(thien-3-yl)imidazolidine-2,4-dione analogs

  摘要：

  A series of twenty optically pure 3-(thien-3-yl) imidazolidine-2,4-dione derivatives have been synthesized in 41-89% yield on treatment of 1H-thieno[3,2-d][1,3]oxazine-2,4-dione with all natural a-amino acids in a quick one-pot microwave-assisted procedure. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.057
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸 在 三乙胺 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 2.5h， 生成 (S)-3-(3-(1-carboxy-2-phenylethyl)ureido)thiophene-2-carboxylic acid
  参考文献：
  名称：

  Exploring the chemical space of ureidothiophene-2-carboxylic acids as inhibitors of the quorum sensing enzyme PqsD from Pseudomonas aeruginosa

  摘要：

  Pseudomonas aeruginosa employs a quorum sensing (QS) communication system that makes use of small diffusible molecules. Among other effects, the QS system coordinates the formation of biofilm which decisively contributes to difficulties in the therapy of Pseudomonas infections. The present work deals with the structure-activity exploration of ureidothiophene-2-carboxylic acids as inhibitors of PqsD, a key enzyme in the biosynthetic pathway of signal molecules in the Pseudomonas QS system. We describe an improvement of the inhibitory activity by successfully combining features from two different PqsD inhibitor classes. Furthermore the functional groups, which are responsible for the inhibitory potency, were identified. Moreover, the inability of the new inhibitors, to prevent signal molecule formation in whole cell assays, is discussed. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.007