(E)-2-(4-chlorobenzylidene)-4-hydroxy-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-(4-chlorobenzylidene)-4-hydroxy-2,3-dihydro-1H-inden-1-one
• 英文别名: (2E)-2-[(4-chlorophenyl)methylidene]-4-hydroxy-3H-inden-1-one
• 化学式: C₁₆H₁₁ClO₂
• 分子量: 270.715
• InChiKey: HQPGYYFEXMQWST-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氢化肉桂酸内酯 在 盐酸 、 aluminum (III) chloride 、 sodium chloride 作用下， 以 甲醇 为溶剂， 反应 27.5h， 生成 (E)-2-(4-chlorobenzylidene)-4-hydroxy-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  2 –苄叉基–1 –茚满酮类似物作为潜在的神经疾病治疗双腺苷A1 / A2a受体拮抗剂。

  摘要：

  先前的研究探索了2-苄基-1-四氢萘酮衍生物作为创新的腺苷A1和A2A受体拮抗剂，用于帕金森氏病的替代性非多巴胺能治疗。这项研究的目的是研究与结构相关的2-亚苄基-1-茚满酮，在环A和B上进行取代，作为新型，有效和选择性的腺苷A1和A2A受体阻滞剂。通过酸催化的醛醇缩合反应合成2-苄叉基-1-茚满酮衍生物，并通过放射性配体结合测定法进行评估，以确定结构活性关系来控制A1和A2A AR亲和力。结果表明，与在C5（2D）处的取代相比，在2-亚苄基-1-茚满酮骨架（2C :)的A环C4处的羟基取代和B环的间（3'）或对位（4'）取代：）或C6（2E：环A）在微摩尔范围内对腺苷A1受体的活性和选择性。此外，在环B的间位（3'）处用氯取代导致高效且选择性强的腺苷A2A受体拮抗剂化合物2 H：。在执行的GTP位移分析中，化合物2C：和2Q：充当腺苷A1受体拮抗剂。鉴于这些发现，化合物2C：，2 H：，

  DOI：

  10.1055/a-0808-3993

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.
• 2–Benzylidene–1–Indanone Analogues as Dual Adenosine A1/A2a Receptor Antagonists for the Potential Treatment of Neurological Conditions
  作者：HelenaDorathea Janse van Rensburg、LesetjaJ. Legoabe、Gisella Terre’Blanche、MiethaM. Van der Walt

  DOI：10.1055/a-0808-3993

  日期：2019.7

  of ring B with chlorine lead to the highly potent and selective adenosine A2A receptor antagonist, compound 2 H: . Compound 2C: and the 2Q: behaved as adenosine A1 receptor antagonists in the performed GTP shift assays. In view of these findings, compounds 2C: , 2 H: , 2Q: and 2P: are potent and selective adenosine A1 and A2A receptor antagonists for the potential treatment of neurological conditions

  先前的研究探索了2-苄基-1-四氢萘酮衍生物作为创新的腺苷A1和A2A受体拮抗剂，用于帕金森氏病的替代性非多巴胺能治疗。这项研究的目的是研究与结构相关的2-亚苄基-1-茚满酮，在环A和B上进行取代，作为新型，有效和选择性的腺苷A1和A2A受体阻滞剂。通过酸催化的醛醇缩合反应合成2-苄叉基-1-茚满酮衍生物，并通过放射性配体结合测定法进行评估，以确定结构活性关系来控制A1和A2A AR亲和力。结果表明，与在C5（2D）处的取代相比，在2-亚苄基-1-茚满酮骨架（2C :)的A环C4处的羟基取代和B环的间（3'）或对位（4'）取代：）或C6（2E：环A）在微摩尔范围内对腺苷A1受体的活性和选择性。此外，在环B的间位（3'）处用氯取代导致高效且选择性强的腺苷A2A受体拮抗剂化合物2 H：。在执行的GTP位移分析中，化合物2C：和2Q：充当腺苷A1受体拮抗剂。鉴于这些发现，化合物2C：，2 H：，