(E)-2-(3-hydroxybenzylidene)-2, 3-dihydro-1H-inden-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (E)-2-(3-hydroxybenzylidene)-2, 3-dihydro-1H-inden-1-one
• 英文别名: (2E)-2-[(3-hydroxyphenyl)methylidene]-3H-inden-1-one
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: VZFZVGDXSOHJRK-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间羟基苯甲醛 、 1-茚酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.58h， 以67.8%的产率得到(E)-2-(3-hydroxybenzylidene)-2, 3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Discovery and structure-activity relationship studies of 2-benzylidene-2,3-dihydro-1H-inden-1-one and benzofuran-3(2H)-one derivatives as a novel class of potential therapeutics for inflammatory bowel disease

  摘要：

  To develop effective therapeutics for inflammatory bowel disease (IBD), 2-benzylidene-2,3-dihydro-1-Hinden-1-one and benzofuran-3(2H)-one derivatives, were designed and synthesized and their structure activity relationships (SAR) were investigated. Compounds 7, 25, 26, 32, 39, 41, 52, 54, and 55 showed potent inhibitory effect (>70%) on the TNF-alpha-induced adhesion of monocytes to colon epithelial cells, which is one of the hallmark events leading to IBD. Such inhibitory activity of the compounds correlated with their suppressive activities against the TNF-alpha-induced production of ROS; ICAM-1 and MCP-1 expression, critical molecules involved in monocyte-epithelial adhesion; and NF-kappa B transcriptional activity. In addition, compounds 41 and 55 significantly suppressed the lipopolysaccharide (LPS)-induced expression of the TNF-alpha gene, with compound 55 showing better efficacy. This inhibition of TNF-alpha expression by compounds 41 and 55 corresponded to their additional inhibitory activity against AP-1 transcriptional activity, which is another transcription factor required for high level TNF-alpha expression. The strong inhibitory activity of compound 55 against an in vivo colitis model was confirmed by its dose dependent inhibitory activity in a rat model of 2,4,6-trinitrobenzenesulfonic acid (TNBS)-induced colitis, demonstrating compound 55 as a new potential candidate for the development of therapeutics against IBD. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.06.018

文献信息

• [EN] NOVEL BENZYLIDENE DIHYDROINDENONE DERIVATIVE, AND COMPOSITION FOR PREVENTING OR TREATING INFLAMMATORY BOWEL DISEASE, CONTAINING SAME<br/>[FR] NOUVEAU DÉRIVÉ DE BENZYLIDÈNE DIHYDROINDÉNONE, ET COMPOSITION POUR PRÉVENIR OU TRAITER UNE MALADIE INTESTINALE INFLAMMATOIRE CONTENANT LE DÉRIVÉ<br/>[KO] 신규한 벤질리덴 디하이드로 인덴온 유도체 및 이를 함유하는 염증성 장질환의 예방 또는 치료용 조성물
  申请人：UNIV YEUNGNAM RES COOPERATION FOUNDATION

  公开号：WO2016195361A1

  公开（公告）日：2016-12-08

  본 발명은 신규한 벤질리덴 디하이드로 인덴온 유도체 및 이를 함유하는 염증성 장질환의 예방 또는 치료용 조성물을 제공한다. 상기 벤질리덴 디하이드로 인덴온 유도체는 소장의 두께 및 대장의 길이를 정상 상태와 같이 유지시키고, 대장에서 우수한 염증 억제 활성을 가짐으로써, 염증성 장질환의 예방 또는 치료에 유용하게 사용할 수 있다.