3-(3,4-dihydroxyphenyl)-N-methylpropanamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(3,4-dihydroxyphenyl)-N-methylpropanamide
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: JVUOHGAGHQZZJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-二羟基苯基丙酸 在 咪唑 、 盐酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.5h， 生成 3-(3,4-dihydroxyphenyl)-N-methylpropanamide
  参考文献：
  名称：

  Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD

  摘要：

  A new strategy for treating Pseudomonas aeruginosa infections could be disrupting the Pseudomonas Quinolone Signal (PQS) quorum sensing (QS) system. The goal is to impair communication among the cells and, hence, reduce the expression of virulence factors and the formation of biofilms. PqsD is an essential enzyme for the synthesis of PQS and shares some features with chalcone synthase (CHS2), an enzyme expressed in Medicago sativa. Both proteins are quite similar concerning the size of the active site, the catalytic residues and the electrostatic surface potential at the entrance of the substrate tunnel. Hence, we evaluated selected substrates of the vegetable enzyme as potential inhibitors of the bacterial protein. This similarity-guided approach led to the identification of a new class of PqsD inhibitors having a catechol structure as an essential feature for activity, a saturated linker with two or more carbons and an ester moiety bearing bulky substituents. The developed compounds showed PqsD inhibition with IC50 values in the single-digit micromolar range. The binding mode of these compounds was investigated by Surface Plasmon Resonance (SPR) experiments revealing that their interaction with the protein is not influenced by the presence of the anthranilic acid bound to active site cysteine. Importantly, some compounds reduced the signal molecule production in cellulo. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.055

文献信息

• [EN] MULTIMODAL CONTRAST AND RADIOPHARMACEUTICAL AGENT FOR AN IMAGING AND A TARGETED THERAPY GUIDED BY IMAGING<br/>[FR] AGENT DE CONTRASTE ET RADIO-PHARMACEUTIQUE MULTIMODAL DESTINÉ À UNE IMAGERIE ET À UNE THÉRAPIE CIBLÉE GUIDÉE PAR IMAGERIE
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2013072071A1

  公开（公告）日：2013-05-23

  The present invention relates to a multimodal contrast and radiopharmaceutical agent for an imaging and a targeted therapy guided by imaging.

  本发明涉及一种用于成像和由成像引导的靶向治疗的多模式对比和放射性药剂。
• Peg-based adhesive phenylic derivatives and methods of synthesis and use
  申请人：MURPHY John L.

  公开号：US20160032047A1

  公开（公告）日：2016-02-04

  The invention provides compositions that use phenylic derivatives to provide adhesive properties. Selection of phenylic derivatives with linkers or linking groups, and the linkages between the linkers or linking groups with polyalkylene oxides, provided herein may be configured to control curing time, biodegradation and/or swelling.

  本发明提供了使用苯基衍生物作为黏合剂的组合物。本发明提供了苯基衍生物与连接剂或连接基团的选择，以及连接剂或连接基团与聚烷氧化物之间的连接，可以配置以控制固化时间、生物降解和/或肿胀。
• Catechol derivatives and pharmaceutical preparations containing same
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0333522A2

  公开（公告）日：1989-09-20

  Catechol derivatives which produce nerve growth factor in particular tissues of the brain are disclosed. These derivatives provide preventive and therapeutic effects for regressive disorders of the central nervous system including senile dementia of the Alzheimer type.

  本研究公开了能在大脑特定组织中产生神经生长因子的儿茶酚衍生物。这些衍生物对包括阿尔茨海默型老年痴呆症在内的中枢神经系统退行性疾病具有预防和治疗作用。
• US5232923A
  申请人：——

  公开号：US5232923A

  公开（公告）日：1993-08-03
• Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD
  作者：Giuseppe Allegretta、Elisabeth Weidel、Martin Empting、Rolf W. Hartmann

  DOI：10.1016/j.ejmech.2014.11.055

  日期：2015.1

  A new strategy for treating Pseudomonas aeruginosa infections could be disrupting the Pseudomonas Quinolone Signal (PQS) quorum sensing (QS) system. The goal is to impair communication among the cells and, hence, reduce the expression of virulence factors and the formation of biofilms. PqsD is an essential enzyme for the synthesis of PQS and shares some features with chalcone synthase (CHS2), an enzyme expressed in Medicago sativa. Both proteins are quite similar concerning the size of the active site, the catalytic residues and the electrostatic surface potential at the entrance of the substrate tunnel. Hence, we evaluated selected substrates of the vegetable enzyme as potential inhibitors of the bacterial protein. This similarity-guided approach led to the identification of a new class of PqsD inhibitors having a catechol structure as an essential feature for activity, a saturated linker with two or more carbons and an ester moiety bearing bulky substituents. The developed compounds showed PqsD inhibition with IC50 values in the single-digit micromolar range. The binding mode of these compounds was investigated by Surface Plasmon Resonance (SPR) experiments revealing that their interaction with the protein is not influenced by the presence of the anthranilic acid bound to active site cysteine. Importantly, some compounds reduced the signal molecule production in cellulo. (C) 2014 Elsevier Masson SAS. All rights reserved.