3-(3-nitrobenzamido)propanoic 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: 3-(3-nitrobenzamido)propanoic acid
• 英文别名: N-(3-nitro-benzoyl)-β-alanine；N-(3-Nitro-benzoyl)-β-alanin；N-[(3-nitrophenyl)carbonyl]-beta-alanine；3-[(3-nitrobenzoyl)amino]propanoic acid
• 化学式: C₁₀H₁₀N₂O₅
• mdl: MFCD00442735
• 分子量: 238.2
• InChiKey: HJXNWCCCIXFBND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  胞嘧啶 、 3-(3-nitrobenzamido)propanoic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以29%的产率得到N-(2-oxo-1,2-dihydropyrimidin-4-yl)-4-(phenylsulfonyl)butanamide
  参考文献：
  名称：

  Design, synthesis, and evaluation of compounds capable of reducing Pseudomonas aeruginosa virulence

  摘要：

  Anti-virulence approaches in the treatment of Pseudomonas aeruginosa (PA)-induced infections have shown clinical potential in multiple in vitro and in vivo studies. However, development of these compounds is limited by several factors, including the lack of molecules capable of penetrating the membrane of gram-negative organisms. Here, we report the identification of novel structurally diverse compounds that inhibit PqsR and LasR-based signaling and diminish virulence factor production and biofilm growth in two clinically relevant strains of P. aeruginosa. It is the first report where potential antivirulent agents were evaluated for inhibition of several virulence factors of PA. Finally, co-treatment with these inhibitors significantly reduced the production of virulence factors induced by the presence of subinhibitory levels of ciprofioxacin. Further, we have analyzed the drug-likeness profile of designed compounds using quantitative estimates of drug-likeness (QED) and confirmed their potential as hit molecules for further development. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.111800
• 作为产物：
  描述：

  间硝基苯甲酰氯 、 β-丙氨酸 生成 3-(3-nitrobenzamido)propanoic acid
  参考文献：
  名称：

  Iodine-containing amino-benzoyl derivatives of amino acids

  摘要：

  公开号：

  US02680133A1

文献信息

• Dérivés d'acide benzamido-alkyl-hydroxamique, procédé de préparation et composition thérapeutique
  申请人：LABORATOIRE L. LAFON Société anonyme dite:

  公开号：EP0061406A1

  公开（公告）日：1982-09-29

  La présente invention concerne, en tant que produits industriels nouveaux, les acides 3-(aminobenzamido)-propionhydroxamiques de formule: et leurs sels d'addition avec les acides. Ces produits sont utiles en thérapeutique. Les composés de formule l peuvent être préparés par hydrogénation catalytique des acides 3-(nitrobenzamido)-propionhydroxamiques correspondants.

  本发明涉及作为新工业产品的式 3-(氨基苯甲酰胺基)丙羟肟酸及其与酸的加成盐： 及其与酸的加成盐。 这些产品具有治疗作用。 式 I 的化合物可通过相应的 3-（硝基苯甲酰胺基）丙羟肟酸的催化氢化反应制备。
• Iodine-containing amino-benzoyl derivatives of amino acids
  申请人：MALLINCKRODT CHEMICAL WORKS

  公开号：US02680133A1

  公开（公告）日：1954-06-01
• US4407822A
  申请人：——

  公开号：US4407822A

  公开（公告）日：1983-10-04
• Design, synthesis, and evaluation of compounds capable of reducing Pseudomonas aeruginosa virulence
  作者：Mohammad Anwar Hossain、Narsimha Sattenapally、Hardik I. Parikh、Wei Li、Kendra P. Rumbaugh、Nadezhda A. German

  DOI：10.1016/j.ejmech.2019.111800

  日期：2020.1

  Anti-virulence approaches in the treatment of Pseudomonas aeruginosa (PA)-induced infections have shown clinical potential in multiple in vitro and in vivo studies. However, development of these compounds is limited by several factors, including the lack of molecules capable of penetrating the membrane of gram-negative organisms. Here, we report the identification of novel structurally diverse compounds that inhibit PqsR and LasR-based signaling and diminish virulence factor production and biofilm growth in two clinically relevant strains of P. aeruginosa. It is the first report where potential antivirulent agents were evaluated for inhibition of several virulence factors of PA. Finally, co-treatment with these inhibitors significantly reduced the production of virulence factors induced by the presence of subinhibitory levels of ciprofioxacin. Further, we have analyzed the drug-likeness profile of designed compounds using quantitative estimates of drug-likeness (QED) and confirmed their potential as hit molecules for further development. Published by Elsevier Masson SAS.