(2E)-2-(pyridin-2-ylmethylidene)-2,3-dihydro-1H-inden-1-one | 4875-91-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (2E)-2-(pyridin-2-ylmethylidene)-2,3-dihydro-1H-inden-1-one
• 英文别名: (E)-2-(pyridin-2-ylmethylene)-2,3-dihydro-1H-inden-1-one；(pyridinylydene-2')-2 indanone；(E)-2-(2'-pyridylmethylene)-1-indanone；2-(2-Pyridyl-methylen)-indanon-(1)；(2E)-2-(pyridin-2-ylmethylidene)-3H-inden-1-one
• CAS: 4875-91-6
• 化学式: C₁₅H₁₁NO
• 分子量: 221.258
• InChiKey: SQKDIBYWOIDSOX-ZRDIBKRKSA-N

物化性质

• 熔点：
  154-155 °C
• 沸点：
  407.9±45.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-2-(pyridin-2-ylmethylidene)-2,3-dihydro-1H-inden-1-one 在 钾硼氢 、 三乙胺 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 N-methyl carbamate de (pyridinylydene-2')-2 indanol
  参考文献：
  名称：

  Fournier; Berthelot; Pavard, European Journal of Medicinal Chemistry, 1981, vol. 16, # 1, p. 48 - 58

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-2-(pyridin-2-ylmethylene)-2,3-dihydro-1H-inden1-one 以 氘代甲苯 为溶剂， 生成 (2E)-2-(pyridin-2-ylmethylidene)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  2-(Pyridin-2-ylmethylene)indan-1-ones：具有缺电子杂芳基的环状查耳酮的 E/Z 异构化的首次研究

  摘要：

  合成吡啶-2-甲醛与1-茚满酮( 4 )、5,6-二甲氧基-1-茚满酮( 5 )和7-乙酰氨基-1-茚满酮( 6 )的缩合产物作为环状查尔酮的衍生物具有缺电子杂环（吡啶），这与早期研究的具有富电子杂环（唑）的类似物不同。所有产品均形成E异构体。X射线分析证实了化合物4的结构。化合物4 – 6的紫外诱导E/Z异构化，以及质子化时发生的转变，通过核磁共振和红外光谱进行了实验研究，并通过 DFT 计算进行了理论上的研究。化合物4的异构化速率远高于5和6的异构化速率。计算了与环外 C C 键有关的所有可能异构体和与吡啶环的 C-C 键有关的旋转异构体。提出了化合物4-6在紫外线照射和质子化作用下转化的一般方案。

  DOI：

  10.1016/j.tet.2022.133005

文献信息

• Superfast synthesis, antibacterial and antifungal studies of halo-aryl and heterocyclic tagged 2,3-dihydro-1H-inden-1-one candidates
  作者：Rahul A. Shinde、Vishnu A. Adole、Bapu S. Jagdale、Thansing B. Pawar

  DOI：10.1007/s00706-021-02772-0

  日期：2021.6

  activities against two Gram-positive (Staphylococcus aureus and Bacillus subtilis) and two Gram-negative bacteria (Escherichia coli and Proteus vulgaris), and also two fungal agents (Aspergillus niger and Candida albicans). Most of the compounds were found to exert potent antibacterial action with broad-spectrum antibacterial activity. Likewise, few compounds were revealed to have potent antifungal properties

  我们描述了卤代芳基和杂环标记的2，3-二氢-1 H-茚满一酮衍生物的成功合成，以及它们的抗菌和抗真菌特性。通过研磨，搅拌和超声辐照方法合成了来自2，3-二氢-1 H-茚基-1-一的总共15种衍生物。这些发现表明，超声技术在时间和合成性能方面越来越令人满意。测试了合成的化合物对两种革兰氏阳性菌（金黄色葡萄球菌和枯草芽孢杆菌）和两种革兰氏阴性菌（大肠杆菌和寻常变形杆菌）以及两种真菌剂的抗菌活性。黑曲霉和白色念珠菌）。发现大多数化合物都具有强大的抗菌作用，并具有广谱抗菌活性。同样，几乎没有化合物显示出对黑曲霉和白色念珠菌具有有效的抗真菌特性。通过FT-IR，1 H NMR，13 C NMR和HRMS光谱技术对合成的化合物进行表征。 图形摘要
• Nicotine receptor ligands
  申请人：Regents of the University of Minnesota

  公开号：US20030027810A1

  公开（公告）日：2003-02-06

  The invention provides nicotine receptor agonists of formula I: 1 wherein R 1 , x, y, and n have any of the values given in the specification, or a pharmaceutically acceptable salt thereof, as well as pharmaceutical compositions comprising such a compound or salt, methods for preparing such a compound or salt, and methods for modulating (e.g. antagonizing or activating) nicotine receptors with such a compound or salt.

  该发明提供了公式I:1中的尼古丁受体激动剂，其中R1、x、y和n可以取规范中给定的任何值，或其药用可接受盐，以及包含这种化合物或盐的药物组合物，制备这种化合物或盐的方法，以及使用这种化合物或盐调节（如拮抗或激活）尼古丁受体的方法。
• [EN] THERAPEUTIC AURONES<br/>[FR] AURONES THÉRAPEUTIQUES
  申请人：MIDDLE TENNESSEE STATE UNIV

  公开号：WO2017180644A1

  公开（公告）日：2017-10-19

  Substituted aurones were found to have antitrypanosomal, antifungal and immunomodulatory activity. The invention provides novel aurone compounds, pharmaceutical compositions, and methods encompassing medical and veterinary applications.

  发现替代的金莲素具有抗锥虫、抗真菌和免疫调节活性。该发明提供了新型金莲素化合物、药物组合物和方法，涵盖医学和兽医应用。
• 2-Heteroarylidene-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.bioorg.2016.09.004

  日期：2016.12

  In the present study a series of fifteen 2-heteroarylidene-1-indanone derivatives were synthesised and evaluated as inhibitors of recombinant human monoamine oxidase (MAO) A and B. These compounds are structurally related to series of heterocyclic chalcone derivatives which have previously been shown to act as MAO-B specific inhibitors. The results document that the 2-heteroarylidene-1-indanones are

  在本研究中，合成了15种2-杂亚芳基-1-茚满酮衍生物，并作为重组人单胺氧化酶（MAO）A和B的抑制剂进行了评估。这些化合物在结构上与一系列先前显示的杂环查尔酮衍生物有关。充当MAO-B特异性抑制剂。结果表明2-杂亚芳基-1-茚满酮是MAO-B的体外抑制剂，显示IC 50值为0.0044-1.53​​μM。尽管其效价较低，但其衍生物还可以抑制具有IC 50的MAO-A同工型值低至0.061μM。对MAO-B抑制的构效关系的分析表明，与A环上的甲氧基取代相比，与未取代的同系物相比，MAO-B抑制作用显着增强，而杂芳族取代基对活性的影响，降序排列为：5-溴-2-呋喃> 5-甲基-2-呋喃> 2-吡啶≈2-噻吩>环己基> 3-吡啶≈2-呋喃。因此可以得出结论，2-杂亚芳基-1-茚满酮衍生物是设计用于治疗帕金森氏病和可能的其他神经退行性疾病的MAO抑制剂的有前途的线索。
• 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.