(E)-3-(3,4-dihydroxyphenyl)-N-(3-nitrophenyl)acrylamide | 1228694-81-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(3,4-dihydroxyphenyl)-N-(3-nitrophenyl)acrylamide
• 英文别名: (E)-3-(3,4-dihydroxyphenyl)-N-(3-nitrophenyl)prop-2-enamide
• CAS: 1228694-81-2
• 化学式: C₁₅H₁₂N₂O₅
• 分子量: 300.271
• InChiKey: HBLQMIRROOWAGN-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  咖啡酸 、 间硝基苯胺 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到(E)-3-(3,4-dihydroxyphenyl)-N-(3-nitrophenyl)acrylamide
  参考文献：
  名称：

  Synthesis, structure and structure–activity relationship analysis of caffeic acid amides as potential antimicrobials

  摘要：

  A series of caffeic acid amides 1-23 were synthesized and nine of which (13-17, 19-21 and 23) were reported for the first time. The chemical structures of these compounds were confirmed by means of H-1 NMR, ESI MS and elemental analyses. Compound 15 was determined by single-crystal X-ray diffraction analysis. All of the compounds were assayed for antibacterial (Bacillus subtilis, Escherichia coli, Pseudomonas fluorescens and Staphylococcus aureus) and antifungal (Aspergillus niger, Candida albicans and Trichophyton rubrum) activities by MTT method. Compounds 10-12, 15, 18 and 21 showed considerable antibacterial activities against B.subtilis with MICs of 795, 625, 389, 118, 312 and 155 mu g/mL, respectively. Structure-activity relationship analysts disclosed that caffeic acid amilides with electron-donating groups at p-position of benzene ring have better inhibitory activities.

  DOI：

  10.1016/j.ejmech.2010.01.066

文献信息

• 신규 클로로겐산 유도체 및 이를 유효성분으로 포함하는 염증성 질환 치료용 조성물
  申请人：Chungbuk National University Industry-Academic Cooperation Foundation 충북대학교 산학협력단(220040168226) BRN ▼301-82-16304

  公开号：KR101693033B1

  公开（公告）日：2017-01-09

  본 발명은 항염증 활성을 갖는 신규 클로로겐산 유도체 화합물 및 이를 유효성분으로 포함하는 항염증 조성물에 관한 것이다. 본 발명의 클로로겐산 유도체 화합물은 대식세포에서 LPS에 처리에 의해 유도되는 산화질소(NO)의 과생성을 억제한다. 본 발명의 클로로겐산 유도체 화합물은 산화적 스트레스 및 염증 촉진 경로에서 중요한 신호전달 매개 전사인자인 NF-κB의 활성화를 저해한다. 본 발명의 클로로겐산 유도체 화합물은 산화질소 과생성과 NF-κB의 활성화를 저해함으로써 다양한 염증성질환의 치료제로 개발될 가능성이 높다.

  本发明涉及具有抗炎活性的新型克罗洛糖酸衍生物化合物及其作为有效成分包含的抗炎组合物。本发明的克罗洛糖酸衍生物化合物可以抑制由大食细胞对LPS处理引起的氧化氮(NO)的过度产生。本发明的克罗洛糖酸衍生物化合物还可以抑制在氧化应激和炎症促进途径中重要的信号传导介质转录因子NF-κB的活化。通过抑制氧化氮的过度产生和NF-κB的活化，本发明的克罗洛糖酸衍生物化合物有望被开发为治疗各种炎症性疾病的治疗剂。
• Synthesis and biological evaluation of caffeic acid derivatives as potent inhibitors of α-MSH-stimulated melanogenesis
  作者：Hyeju Jo、Minho Choi、Jaeuk Sim、Mayavan Viji、Siyuan Li、Young Hee Lee、Youngsoo Kim、Seung-Yong Seo、Yuanyuan Zhou、Kiho Lee、Wun-Jae Kim、Jin Tae Hong、Heesoon Lee、Jae-Kyung Jung

  DOI：10.1016/j.bmcl.2017.06.011

  日期：2017.8

  We have disclosed our effort to develop caffeic acid derivatives as potent and non-toxic inhibitors of α-MSH-stimulated melanogenesis to treat pigmentation disorders and skin medication including a cosmetic skin-whitening agent. The SAR studies revealed that cyclohexyl ester and secondary amide derivatives of caffeic acid showed significant inhibitory activities.

  我们已经公开了开发咖啡酸衍生物作为α-MSH刺激的黑色素生成的有效和无毒抑制剂的努力，以治疗色素沉着症和包括美容性皮肤增白剂的皮肤药物。SAR研究表明，咖啡酸的环己酯和仲酰胺衍生物表现出显着的抑制活性。