2-(3,4-dimethoxybenzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one | 861552-54-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(3,4-dimethoxybenzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one
• 英文别名: 2-[(3,4-dimethoxyphenyl)methylidene]-5,6-dimethoxy-3H-inden-1-one
• CAS: 861552-54-7
• 化学式: C₂₀H₂₀O₅
• 分子量: 340.376
• InChiKey: YOMNDBPQAYZBOD-UHFFFAOYSA-N

物化性质

• 熔点：
  193 °C
• 沸点：
  538.7±50.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxybenzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one 在 吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、550.01 kPa 条件下， 反应 72.0h， 以88%的产率得到2-Veratryl-5,6-dimethoxyindanone
  参考文献：
  名称：

  Centropolyindanes背后的一个难以捉摸的非芳香目标：Veratrolo-带环的Centropolyquinanes和Ozonolytic Abbau的Aufbau

  摘要：

  这项研究提出了一种潜在的实验方法，可通过富电子芳族中心聚茚满烷的结构分解（aufbau – abbau）策略来解决仍难以捉摸的拓扑非平面（K 5）母体碳六六烷（1）。合成了一系列基于Veratrole的Centropolyindane，并进行了臭氧分解降解。这些包括2,2'- spirobiindanes 30 - 32，扶桑-diindane 33，triptindanes 34 - 36，tribenzotriquinacene 37，和tetramethoxycentrohexaindane 9。尖塔30X射线结构分析表征了螺旋桨36和螺旋桨36。臭氧分解32和33分别得到酮酸酯（59）和粘康酸二甲酯（60）。二甲氧基三tin烷34以良好的产率得到[3.3.3]丙炔-顺式，顺式-粘康酸酯（61），其立体化学通过X射线结构分析确定。四甲氧基三丁烷35给出[3.3.3]丙二酸双粘康酸酯62和[3

  DOI：

  10.1002/cplu.201700090
• 作为产物：
  描述：

  5,6-二甲氧基茚酮 在 chromium(VI) oxide 、 溶剂黄146 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 73.0h， 生成 2-(3,4-dimethoxybenzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Centropolyindanes背后的一个难以捉摸的非芳香目标：Veratrolo-带环的Centropolyquinanes和Ozonolytic Abbau的Aufbau

  摘要：

  这项研究提出了一种潜在的实验方法，可通过富电子芳族中心聚茚满烷的结构分解（aufbau – abbau）策略来解决仍难以捉摸的拓扑非平面（K 5）母体碳六六烷（1）。合成了一系列基于Veratrole的Centropolyindane，并进行了臭氧分解降解。这些包括2,2'- spirobiindanes 30 - 32，扶桑-diindane 33，triptindanes 34 - 36，tribenzotriquinacene 37，和tetramethoxycentrohexaindane 9。尖塔30X射线结构分析表征了螺旋桨36和螺旋桨36。臭氧分解32和33分别得到酮酸酯（59）和粘康酸二甲酯（60）。二甲氧基三tin烷34以良好的产率得到[3.3.3]丙炔-顺式，顺式-粘康酸酯（61），其立体化学通过X射线结构分析确定。四甲氧基三丁烷35给出[3.3.3]丙二酸双粘康酸酯62和[3

  DOI：

  10.1002/cplu.201700090

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。
• Multitarget-Directed Benzylideneindanone Derivatives: Anti-β-Amyloid (Aβ) Aggregation, Antioxidant, Metal Chelation, and Monoamine Oxidase B (MAO-B) Inhibition Properties against Alzheimer’s Disease
  作者：Ling Huang、Chuanjun Lu、Yang Sun、Fei Mao、Zonghua Luo、Tao Su、Huailei Jiang、Wenjun Shan、Xingshu Li

  DOI：10.1021/jm300978h

  日期：2012.10.11

  A novel series of benzylideneindanone derivatives were designed, synthesized, and evaluated as multitarget-directed ligands against Alzheimer's disease. The in vitro studies showed that most of the molecules exhibited a significant ability to inhibit self-induced beta-amyloid (A beta(1-42)) aggregation (10.5-80.1%, 20 mu M) and MAO-B activity (IC50 of 7.5-40.5 mu M), to act as potential antioxidants (ORAC-FL value of 2.75-9.37), and to function as metal chelators. In particular, compound 41 had the greatest ability to inhibit A beta(1-42) aggregation (80.1%), and MAO-B (IC50 = 7.5 mu M) was also an excellent antioxidant and metal chelator. Moreover, it is capable of inhibiting Cu(II)-induced A beta(1-42) aggregation and disassembling the well-structured A beta fibrils. These results indicated that compound 41 is an excellent multifunctional agent for the treatment of AD.
• 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.