2-benzylidene-5,6-dimethoxy-3H-inden-1-one | 861595-05-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-benzylidene-5,6-dimethoxy-3H-inden-1-one
• CAS: 861595-05-3
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: OFGKZKHSXFVVBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzylidene-5,6-dimethoxy-3H-inden-1-one 、 S-(4-叔-丁基苯甲基)[2-(1-甲基丁基)吡啶-3-基]硫代氨基甲酸酯 在 溶剂黄146 作用下， 反应 12.0h， 以72%的产率得到3-phenyl-6,7-dimethoxy-3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide
  参考文献：
  名称：

  Synthesis and antimycobacterial evaluation of 3a,4-dihydro-3H-indeno [1,2-c] pyrazole-2-carboxamide analogues

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2011.09.035
• 作为产物：
  描述：

  5,6-二甲氧基茚酮 、 苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2-benzylidene-5,6-dimethoxy-3H-inden-1-one
  参考文献：
  名称：

  A Facile Ionic Liquid Promoted Synthesis, Cholinesterase Inhibitory Activity and Molecular Modeling Study of Novel Highly Functionalized Spiropyrrolidines

  摘要：

  在离子液体[bmim]Br中合成了一系列新型二甲基氧代茚满嵌段螺吡咯烷，并评估了其对胆碱酯酶的抑制活性。在螺吡咯烷中，化合物4f对乙酰胆碱酯酶（AChE）表现出最强的活性，IC50值为1.57 µM。对活性最高的化合物进行了分子对接模拟，以揭示其与AChE受体活性位点的结合机制。

  DOI：

  10.3390/molecules20022296

文献信息

• Ionic Liquid-Promoted Synthesis and Cholinesterase Inhibitory Activity of Highly Functionalized Spiropyrrolidines
  作者：Raju Suresh Kumar、Abdulrahman I. Almansour、Natarajan Arumugam、Alireza Basiri、Yalda Kia、Raju Ranjith Kumar

  DOI：10.1071/ch14370

  日期：——

  A library of novel, highly functionalized spiropyrrolidines has been synthesized stereoselectively for the first time in ionic liquid medium employing [3+2] cycloaddition of a series of 2-arylmethylidene-5,6-dimethoxy-2,3-dihydro-1H-inden-1-ones with an unexplored azomethine ylide derived from acenaphthenequinone or isatin and tryptophan. These compounds were evaluated in vitro for their acetylcholinesterase and butyrylcholinesterase inhibitory activities. Molecular modelling simulation was performed to determine the binding interaction and orientation of these molecules in the active site gorge of the respective receptors.

  我们首次在离子液体介质中利用一系列 2-芳基亚甲基-5,6-二甲氧基-2,3-二氢-1H-茚-1-酮与源自苊醌或异atin 和色氨酸的一种未探索的偶氮甲基醯化物的[3+2]环加成，立体选择性地合成了一批新型、高官能度的螺吡咯烷类化合物。对这些化合物的乙酰胆碱酯酶和丁酰胆碱酯酶抑制活性进行了体外评估。进行了分子建模模拟，以确定这些分子在各自受体活性位点峡谷中的结合相互作用和取向。
• 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。
• 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.