2-(4-fluorobenzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one | 1260498-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(4-fluorobenzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one
• CAS: 1260498-70-1
• 化学式: C₁₈H₁₅FO₃
• 分子量: 298.314
• InChiKey: CXVUQUFOBMBLCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 2-(4-fluorobenzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one 在 十六烷基三甲基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以83%的产率得到2-[4-(N-methylpiperazinebenzylidene)]-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  从芳香亲核取代 (SNAr) 反应合成 2-(4-氨基取代亚苄基) 茚满酮类似物

  摘要：

  摘要 开发了一种新型、高效、方便的合成 2-(4-氨基取代亚苄基)茚满酮衍生物的方法。在第一步中，描述了 4-氟苯甲醛与 5, 6-二甲氧基-2, 3-二氢-1H-inden-1-one 在 NaOH 和 EtOH 中的反应。在下一步中，各种脂肪族和芳香族胺与 2-(4-fluorobenzylidene)-5, 6-dimethoxy-2, 3-dihydro-1H-Inden-1-one 通过芳香取代 (SNAr) 反应得到产生 2-(4-aminobenzlidene)-5, 6-dimethoxy-2, 3-dihydro-1H-Inden-1-one 衍生物作为一类新的 1-indanones。这些产品已成功制备，收率非常好。1 H 和 13 C NMR、FT-IR 光谱和 CHN 分析支持产品的拟议结构。图形概要

  DOI：

  10.1080/00397911.2018.1492726
• 作为产物：
  描述：

  5,6-二甲氧基茚酮 、 对氟苯甲醛 以 乙醇 、 水 为溶剂， 以86%的产率得到2-(4-fluorobenzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  一种方便有效的合成新的2-（4-氨基取代的苄基吡啶）茚满酮衍生物的方法

  摘要：

  已经开发了用于合成新型1-茚满酮衍生物的有效且改进的方法。在提出的新方法的第一步中，通过相应化合物与各种脂肪族和芳香族胺的N-芳基化反应，4-溴苯甲醛与5、6-二甲氧基-2、3-二氢-1 H-茚满一酮反应作为最后一步，生产出新颖的1-indanones类。这种新设计的方法与常规方法的比较表明，我们的方法在产生更高的总产量方面更为有效。这种创新的合成方法具有许多优势，其中便宜的试剂的消耗以及最终产品更高的总收率是其显着优势。

  DOI：

  10.1007/s11164-016-2549-0

文献信息

• Substituted spiro [2.3′] oxindolespiro [3.2″]-5,6-dimethoxy-indane-1″-one-pyrrolidine analogue as inhibitors of acetylcholinesterase
  作者：Mohamed Ashraf Ali、Rusli Ismail、Tan Soo Choon、Yeong Keng Yoon、Ang Chee Wei、Suresh Pandian、Raju Suresh Kumar、Hasnah Osman、Elumalai Manogaran

  DOI：10.1016/j.bmcl.2010.09.108

  日期：2010.12

  Series of pyrolidine analogues were synthesized and examined as acetylcholinesterase (AChE) inhibitors. Among the compounds, compounds 4k and 6k were the most potent inhibitors of the series. Compound 4k, showed potent inhibitory activity against acetyl cholinesterase enzyme with IC50 0.10 μmol/L. Pyrolidine analogues might be potential acetyl cholinesterase agents for AD.

  合成了一系列吡咯烷类似物，并作为乙酰胆碱酯酶（AChE）抑制剂进行了研究。在这些化合物中，化合物4k和6k是该系列中最有效的抑制剂。化合物4k对乙酰胆碱酯酶显示出有效的抑制活性，IC 50为0.10μmol/ L。吡咯烷类似物可能是AD的潜在乙酰胆碱酯酶药物。
• Multifunctional indanone–chalcone hybrid compounds with anti-β-amyloid (Aβ) aggregation, monoamine oxidase B (MAO-B) inhibition and neuroprotective properties against Alzheimer’s disease
  作者：Keren Wang、Lintao Yu、Jian Shi、Wenmin Liu、Zhipei Sang

  DOI：10.1007/s00044-019-02423-4

  日期：2019.11

  discover multifunctional agents for the treatment of Alzheimer’s disease (AD), a series of indanone–chalcone hybrid compounds were designed and synthesized based on the multitarget-directed ligand strategy. Their monoamino oxidases (MAO-A and MAO-B) and Aβ1–42 aggregation inhibitory activities were evaluated. The results were shown that all synthetic compounds exhibited mostly good multifunctional activities

  为了发现用于治疗阿尔茨海默氏病（AD）的多功能药物，基于多靶标定向配体策略设计并合成了一系列茚满酮-查尔酮杂化化合物。评估了它们的单氨基氧化酶（MAO-A和MAO-B）和Aβ1–42聚集抑制活性。结果表明，所有合成化合物均表现出良好的多功能活性。它们之中，化合物TM-11表示的最好的甲β 1-42聚集抑制效力（IC 50  〜1.8μM）和良好的解聚作用的活性（IC 50  〜7.9微米）。TEM图像和对接研究都为该假设提供了良好的合理解释。同时，化合物TM-11是一种选择性MAO-B抑制剂，以及针对A中的神经保护剂β 1-42诱导的毒性。基于结构上的考虑，化合物TM-11的亲脂性可根据Lipinski的5法则在体外穿过血脑屏障（BBB）。总之，这些结果表明，化合物TM-11可能是治疗AD的潜在多功能剂。
• POMA analyses as new efficient bioinformatics’ platform to predict and optimise bioactivity of synthesized 3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide/carbothioamide analogues
  作者：Mohamed Jawed Ahsan、Jeyabalan Govindasamy、Habibullah Khalilullah、Govind Mohan、James P. Stables、Christophe Pannecouque、Eric De Clercq

  DOI：10.1016/j.bmcl.2012.09.108

  日期：2012.12

  A series of 43, 3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide/carbothioamide analogues (D01-D43) were analysed using Petra, Osiris, Molinspiration and ALOGPS (POMA) to identify pharmacophore, toxicity prediction, lipophilicity and bioactivity. All the compounds were evaluated for anti-HIV activity. 3-(4-Chlorophenyl)-N-(4-fluorophenyl)-6,7-dimethoxy-3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide (D07) was found to be the most active with IC50 > 4.83 mu M and CC50 4.83 mu M. 3-(4-Fluorophenyl)-6,7-dimethoxy-3a, 4-dihydro-3H-indeno[1,2-c]pyrazole-2-carbothioamide (D41) was found to be the most active compound against bacterial strains with MIC of 4 mu g/ml, comparable to the standard drug ciprofloxacin while 3-(4-methoxyphenyl)-6,7-dimethoxy-3a, 4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide (D38) was found to be the most active compound against fungal strains with MIC 2-4 mu g/ml, however less active than standard fluconazole. Toxicities prediction by Osiris were well supported and experimentally verified with exception of some compounds. In anticonvulsant screening, 3-(4-fluorophenyl)-N-(4-chlorophenyl)-6,7-dimethoxy-3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide (D09) showed maximum activity showing 100% (4/4, 0.25-0.5 h) and 75% (3/4, 1.0 h) protection against minimal clonic seizure test without any toxicity. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and anticonvulsant activity of 3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide/carbothioamide analogues
  作者：Mohamed Jawed Ahsan、Habibullah Khalilullah、James P. Stables、Jeyabalan Govindasamy

  DOI：10.3109/14756366.2012.663364

  日期：2013.6.1

  A series of fourteen 3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide/carbothioamide analogues were synthesized and evaluated for anticonvulsant activity according to the Antiepileptic Drug Development Programme (ADD) protocol. Some of the synthesized compounds showed significant activity in minimal clonic seizure model (6 Hz psychomotor seizure test). 3-(4-Fluorophenyl)-N-(4-bromophenyl)-6,7-dimethoxy-3a,4-dihydro-3H-indeno[1,2-c] pyrazole-2-carboxamide (4c) was found to be the most active compound of the series showing 75% (3/4, 0.25-2.0 h) and 50% (2/4, 4.0 h) protection against minimal clonic seizure at 100 mg/kg without any toxicity. 3-(Pyridin-4-yl)-N-(4-chlorophenyl)-6,7-dimethoxy-3a, 4-dihydro-3H-indeno[1,2-c] pyrazole-2-carboxamide (4f) showed protection in maximal electroshock (MES) seizure and subcutaneous metrazol (scMET) seizure at 300 mg/kg.
• Synthesis and antimycobacterial evaluation of 3a,4-dihydro-3H-indeno [1,2-c] pyrazole-2-carboxamide analogues
  作者：Mohamed Jawed Ahsan、Jeyabalan Govinda Samy、Habibullah Khalilullah、Mohamed Afroz Bakht、Mohd. Zaheen Hassan

  DOI：10.1016/j.ejmech.2011.09.035

  日期：2011.11

  In the present investigation, a series of 3a,4-dihydro-3H-indeno [1,2-c] pyrazole-2-carboxamide analogues were synthesized and were evaluated for antitubercular activity by two fold serial dilution technique. All the newly synthesized compounds showed low to good inhibitory activities against Mycobacterium tuberculosis H(37)Rv and multi-drug resistant M. tuberculosis (MDR-TB). 3-(4-fluorophenyl)-N-(4-chlorophenyl)-6,7-dimethoxy-3a,4-dihydro-3H-indeno [1,2-c] pyrazole-2-carboxamide (4c) was found to be the most promising compound active against M. tuberculosis, H37Rv and MDR-TB with minimum inhibitory concentrations 0.83 mu M and 332 mu M respectively. (C) 2011 Elsevier Masson SAS. All rights reserved.