(E)-5-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: (E)-5-hydroxy-2-(3-hydroxybenzylidene)-2,3-dihydro-1H-inden-1-one
• 英文别名: (2E)-5-hydroxy-2-[(3-hydroxyphenyl)methylidene]-3H-inden-1-one
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: KUFVDOFKDZGYOH-WUXMJOGZSA-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：

  5-羟基-1-茚酮 、 间羟基苯甲醛 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以36%的产率得到(E)-5-hydroxy-2-(3-hydroxybenzylidene)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  2-苄叉基-1-茚满酮衍生物作为单胺氧化酶的抑制剂。

  摘要：

  在本研究中，合成了一系列的22个2-亚苄基-1-茚满酮衍生物，并将其作为重组人单胺氧化酶（MAO）A和B的抑制剂。一系列的亚苄基茚满酮衍生物，以前发现它们是MAO-B抑制剂。该研究发现2-亚苄基-1-茚满酮是MAO-B特异性抑制剂，IC50值<2.74μM。在所评估的化合物中，有十二种化合物的IC50 <0.1μM，可被视为高效抑制剂。2-亚苄基-1-茚满酮衍生物还抑制MAO-A，最强的抑制作用是5g（IC50 =0.131μM）。对MAO-B抑制的构效关系的分析表明，在A环上被5-羟基取代，在B环上被卤素和甲基取代产生了高效抑制作用。因此可以得出结论，2-亚苄基-1-茚满酮类似物是用于设计诸如帕金森氏病的疗法的有前途的线索。

  DOI：

  10.1016/j.bmcl.2016.08.067

文献信息

• 2-Benzylidene-1-indanone derivatives as inhibitors of monoamine oxidase
  作者：Magdalena S. Nel、Anél Petzer、Jacobus P. Petzer、Lesetja J. Legoabe

  DOI：10.1016/j.bmcl.2016.08.067

  日期：2016.10

  In the present study, a series of twenty-two 2-benzylidene-1-indanone derivatives were synthesised and evaluated as inhibitors of recombinant human monoamine oxidase (MAO) A and B. The 2-benzylidene-1-indanone derivatives are structurally related to a series of benzylideneindanone derivatives which has previously been found to be MAO-B inhibitors. This study finds that the 2-benzylidene-1-indanones

  在本研究中，合成了一系列的22个2-亚苄基-1-茚满酮衍生物，并将其作为重组人单胺氧化酶（MAO）A和B的抑制剂。一系列的亚苄基茚满酮衍生物，以前发现它们是MAO-B抑制剂。该研究发现2-亚苄基-1-茚满酮是MAO-B特异性抑制剂，IC50值<2.74μM。在所评估的化合物中，有十二种化合物的IC50 <0.1μM，可被视为高效抑制剂。2-亚苄基-1-茚满酮衍生物还抑制MAO-A，最强的抑制作用是5g（IC50 =0.131μM）。对MAO-B抑制的构效关系的分析表明，在A环上被5-羟基取代，在B环上被卤素和甲基取代产生了高效抑制作用。因此可以得出结论，2-亚苄基-1-茚满酮类似物是用于设计诸如帕金森氏病的疗法的有前途的线索。
• [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.
• 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.