(E)-2-(4-hydroxybenzylidene)-2,3-dihydro-1H-inden-1-one | 124996-01-6

• 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-(4-hydroxybenzylidene)-2,3-dihydro-1H-inden-1-one
• 英文别名: (E)-2-(4-hydroxybenzyliden)-2,3-dihydro-1H-inden-1-one；2(p-hydroxy-benzylidene)-1-indanone；4-(1-oxoindan-2-ylidenemethyl)phenol；(e)-2-(4'-Hydroxybenzylidene)-1-indanone；(2E)-2-[(4-hydroxyphenyl)methylidene]-3H-inden-1-one
• CAS: 124996-01-6
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: DRPPCEHRGYFXHN-UKTHLTGXSA-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

• 作为反应物：
  描述：

  (E)-2-(4-hydroxybenzylidene)-2,3-dihydro-1H-inden-1-one 、 对甲苯磺酰肼 在 对甲苯磺酸 作用下， 以 乙醇 、 乙酸乙酯 、 Petroleum ether 为溶剂， 生成 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenol
  参考文献：
  名称：

  Tricyclic pyrazole derivatives

  摘要：

  这项发明涉及具有4,5(3,4)-双环融合的3-芳基或3-杂芳基吡唑，这些化合物是蛋白激酶活性抑制剂，其中一些是新颖化合物，涉及含有这些吡唑的药物组合物以及制备这些吡唑的方法。

  公开号：

  US06462036B1
• 作为产物：
  描述：

  2-[(E)-4-methoxyphenylmethylidene]-1-indanone 在 吡啶盐酸盐 作用下， 反应 0.42h， 以93%的产率得到(E)-2-(4-hydroxybenzylidene)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Sinha, Anoop Kumar; Rastogi, Shri Nivas, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 7, p. 684 - 692

  摘要：

  DOI：

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.
• In vitro and in silico insights into tyrosinase inhibitors with (E)-benzylidene-1-indanone derivatives
  作者：Hee Jin Jung、Sang Gyun Noh、Yujin Park、Dongwan Kang、Pusoon Chun、Hae Young Chung、Hyung Ryong Moon

  DOI：10.1016/j.csbj.2019.07.017

  日期：——

  Tyrosinase is a key enzyme responsible for melanin biosynthesis and is effective in protecting skin damage caused by ultraviolet radiation. As part of ongoing efforts to discover potent tyrosinase inhibitors, we systematically designed and synthesized thirteen (E)-benzylidene-l-indanone derivatives (BID1-13) and determined their inhibitory activities against tyrosinase. Among the compounds evaluated, BID3 was the most potent inhibitor of mushroom tyrosinase (IC50 = 0.034 mu M, monophenolase activity; IC50 = 1.39 mu M, diphenolase activity). Kinetic studies revealed that BID3 demonstrated a mixed type of tyrosinase inhibition with K-i value of 2.4 mu M using L-DOPA as a substrate. In silico molecular docking simulations demonstrated that BID3 can bind to the catalytic and allosteric sites of tyrosinase to inhibit enzyme activity which confirmed in vitro experimental studies between BID3 and tyrosinase. Furthermore, melanin contents decreased and cellular tyrosinase activity was inhibited after BID3 treatment. These observations revealed that BID3 is a potent tyrosinase inhibitor and potentially could be used as a whitening agent for the treatment of pigmentation-related disorders. (C) 2019 The Authors. Published by Elsevier B.V. on behalf of Research Network of Computational and Structural Biotechnology.
• KIRKIACHARIAN, SERGE;GOMIS, MICHEL;KOUTSOURAKIS, PANTELIS, EUR. J. MED. CHEM., 24,(1989) N, C. 309-311
  作者：KIRKIACHARIAN, SERGE、GOMIS, MICHEL、KOUTSOURAKIS, PANTELIS

  DOI：——

  日期：——
• MOUSSA, H. H.;SHAFIK, N. A., EGYPT. J. CHEM., 1983, 26, N 6, 533-540
  作者：MOUSSA, H. H.、SHAFIK, N. A.

  DOI：——

  日期：——
• TRICYCLIC PYRAZOLE DERIVATIVES
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP1127051A2

  公开（公告）日：2001-08-29