(2E)-4-hydroxy-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: (2E)-4-hydroxy-2-(3-hydroxybenzylidene)-2,3-dihydro-1H-inden-1-one
• 英文别名: (E)-4-hydroxy-2-(3-hydroxybenzylidene)-2,3-dihydro-1H-inden-1-one；(2E)-4-hydroxy-2-[(3-hydroxyphenyl)methylidene]-3H-inden-1-one
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: BGTZJYVFLMFMCJ-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基-1-茚酮 、 间羟基苯甲醛 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以46%的产率得到(2E)-4-hydroxy-2-(3-hydroxybenzylidene)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  查尔酮基苯并环烷酮衍生物作为腺苷A1和/或A2A受体拮抗剂的合成及其结构活性关系。

  摘要：

  腺苷A1和/或A2A受体拮抗剂有望用于治疗神经系统疾病，如帕金森氏病。本文中，总共合成了十七种苯并环烷酮衍生物，并评估了其对腺苷受体（A1和A2A AR）的亲和力。获得的结果可以得出这样的结论，即2-亚苄基-1-茚满酮和-四氢萘酮衍生物对A1和/或A2A ARs的亲和力和/或选择性可能受取代基（-OH，-OCH3或吗啉）连接在1-茚满酮核心的C4和1-tetralone核心的C5以及B环的间（C3'）和/或对位（C4'）位置。几种化合物（2A： -B：，3B：-C：和4A：-B：）对10 µM以下的A1和/或A2A AR具有亲和力。另外，化合物2A：，3B：和4A：是A1 AR拮抗剂。这些结果再次证实在环A上的C4甲氧基取代基与2-亚苄基-1-茚满酮骨架的间位（C3'）和/或对位（C4'）羟基取代环B结合的重要性导致在纳摩尔范围内具有亲和力的类药物化合物1H：和1J:。

  DOI：

  10.1055/a-1146-2996

文献信息

• 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
  作者：Tara Man Kadayat、Suhrid Banskota、Pallavi Gurung、Ganesh Bist、Til Bahadur Thapa Magar、Aarajana Shrestha、Jung-Ae Kim、Eung-Seok Lee

  DOI：10.1016/j.ejmech.2017.06.018

  日期：2017.9

  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.
• [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.
• Synthesis and Structure Activity Relationships of Chalcone based Benzocycloalkanone Derivatives as Adenosine A1 and/or A2A Receptor Antagonists
  作者：Helena D. Janse van Rensburg、Lesetja J. Legoabe、Gisella Terre’Blanche

  DOI：10.1055/a-1146-2996

  日期：2020.6

  Adenosine A1 and/or A2A receptor antagonists hold promise for the potential treatment of neurological conditions, such as Parkinson's disease. Herein, a total of seventeen benzocycloalkanone derivatives were synthesised and evaluated for affinity towards adenosine receptors (A1 and A2A AR). The obtained results allowed for the conclusion that affinity and/or selectivity of the 2-benzylidene-1-indanone

  腺苷A1和/或A2A受体拮抗剂有望用于治疗神经系统疾病，如帕金森氏病。本文中，总共合成了十七种苯并环烷酮衍生物，并评估了其对腺苷受体（A1和A2A AR）的亲和力。获得的结果可以得出这样的结论，即2-亚苄基-1-茚满酮和-四氢萘酮衍生物对A1和/或A2A ARs的亲和力和/或选择性可能受取代基（-OH，-OCH3或吗啉）连接在1-茚满酮核心的C4和1-tetralone核心的C5以及B环的间（C3'）和/或对位（C4'）位置。几种化合物（2A： -B：，3B：-C：和4A：-B：）对10 µM以下的A1和/或A2A AR具有亲和力。另外，化合物2A：，3B：和4A：是A1 AR拮抗剂。这些结果再次证实在环A上的C4甲氧基取代基与2-亚苄基-1-茚满酮骨架的间位（C3'）和/或对位（C4'）羟基取代环B结合的重要性导致在纳摩尔范围内具有亲和力的类药物化合物1H：和1J:。