(E)-2-(2-chlorobenzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one | 1188401-66-2

• 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-(2-chlorobenzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one
• CAS: 1188401-66-2
• 化学式: C₁₈H₁₅ClO₃
• 分子量: 314.768
• InChiKey: PIOUQOJLOKBZEV-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 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：

  (E)-2-(2-chlorobenzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one 在 盐酸羟胺 、 溶剂黄146 作用下， 反应 15.0h， 生成 3-(2-chlorophenyl)-6,7-dimethoxy-3a,4-dihydro-3H-indeno[1,2-c]isoxazole
  参考文献：
  名称：

  抗分枝杆菌活性：合成新型3-（取代苯基）-6,7-二甲氧基-3a，4-二氢-3H-茚并[1,2-c]异恶唑类似物。

  摘要：

  在这项研究中，合成了一系列新型的3-（取代苯基）-6,7-二甲氧基-3a，4-二氢-3H-茚并[1,2-c]异恶唑类似物，并评估了其对结核分枝杆菌的抗分枝杆菌活性（ H（37）Rv和耐异烟肼结核分枝杆菌（INHR-MTB）。所有新合成的化合物均显示出中等至高抑制活性。发现化合物6,7-二甲氧基-3-（4-氯苯基）-4H-茚并[1,2-c]异恶唑（4b）是最有希望的化合物，对MTB H（37）Rv和INHR具有活性-MTB的最低抑菌浓度为0.22和0.34μM。

  DOI：

  10.3109/14756366.2010.529805
• 作为产物：
  描述：

  5,6-二甲氧基茚酮 、 2-氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 Petroleum ether 为溶剂， 生成 (E)-2-(2-chlorobenzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  抗分枝杆菌活性：合成新型3-（取代苯基）-6,7-二甲氧基-3a，4-二氢-3H-茚并[1,2-c]异恶唑类似物。

  摘要：

  在这项研究中，合成了一系列新型的3-（取代苯基）-6,7-二甲氧基-3a，4-二氢-3H-茚并[1,2-c]异恶唑类似物，并评估了其对结核分枝杆菌的抗分枝杆菌活性（ H（37）Rv和耐异烟肼结核分枝杆菌（INHR-MTB）。所有新合成的化合物均显示出中等至高抑制活性。发现化合物6,7-二甲氧基-3-（4-氯苯基）-4H-茚并[1,2-c]异恶唑（4b）是最有希望的化合物，对MTB H（37）Rv和INHR具有活性-MTB的最低抑菌浓度为0.22和0.34μM。

  DOI：

  10.3109/14756366.2010.529805

文献信息

• AChE inhibitor : A regio- and stereo-selective 1,3-dipolar cycloaddition for the synthesis of novel substituted 5,6-dimethoxy spiro[5.3′]-oxindole-spiro-[6.3″]-2,3-dihydro-1H-inden-1″-one-7-(substituted aryl)-tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole
  作者：Mohamed Ashraf Ali、Rusli Ismail、Tan Soo Choon、Raju Suresh Kumar、Hasnah Osman、Natarajan Arumugam、Abdulrahman I. Almansour、Karthikeyan Elumalai、Abhimanyu Singh

  DOI：10.1016/j.bmcl.2011.10.087

  日期：2012.1

  Pyrrolothiazolyloxindole analogues share vital pharmacological properties, considered useful in Alzheimer’s disease (AD). The aim of this study was synthesis and evaluate pyralothiazolyloxindole analogues if possess acetyl cholinesterase (AChE) inhibitory activity. The easily accessible one-pot synthesis of these compounds resulted to be significantly less difficult and expensive than that of donepezil

  吡咯并噻唑基二恶唑类似物具有重要的药理特性，被认为可用于阿尔茨海默氏病（AD）。这项研究的目的是合成和评估如果具有乙酰胆碱酯酶（AChE）抑制活性的吡咯并噻唑并恶唑类似物。与多奈哌齐相比，这些化合物易于一锅合成的难度和成本明显降低。几种化合物具有微摩尔和亚微摩尔级的抗胆碱酯酶活性。特别是，化合物6a是该系列中最有效的乙酰胆碱酯酶抑制剂，IC 50为0.11μmol/ L。
• A regio- and stereoselective 1,3-dipolar cycloaddition for the synthesis of new-fangled dispiropyrrolothiazoles as antimycobacterial agents
  作者：Abdulrahman I. Almansour、Sadath Ali、Mohamed Ashraf Ali、Rusli Ismail、Tan Soo Choon、Velmurugan Sellappan、Karthi keyan Elumalai、Suresh Pandian

  DOI：10.1016/j.bmcl.2012.10.059

  日期：2012.12

  A series of dispiropyrrolothiazoles compounds were synthesized using 1,3-dipolar cycloaddition and were screened for antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv and INH resistant M. tuberculosis strains. Two of them were showing good activity with MIC of less than 1 mu M. Compound (5f) was found to be the most active with MIC of 0.210 and 8.312 mu M respectively. (c) 2012 Elsevier Ltd. All rights reserved.
• Discovery of novel methanone derivatives acting as antimycobacterial agents
  作者：Mohamed Ashraf Ali、Sylvaine Bastian、Rusli Ismail、Tan Soo Choon、Sadath Ali、Alexandra Aubry、Suresh Pandian、Pankaj Saraswat、Abhimanyu Singh、Ramakant Gaur

  DOI：10.3109/14756366.2011.559945

  日期：2011.12.1

  A series of pyrazoline derivatives were synthesized and in vitro activity against Mycobacterium tuberculosis H37Rv was carried out. Among the synthesized compounds, compounds (4d) and (4f) 4-aminophenyl-3-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3,3a,4-tetrahydroindeno[1,2-c]pyrazol-2-ylmethanone and 4-aminophenyl-6,7-dimethoxy-3-phenyl-2,3,3a, 4-tetrahydroindeno[1,2-c] pyrazol-2-ylmethanone were found to be the most active agent against M. tuberculosis H37Rv with a minimum inhibitory concentration of 10 mu g/mL.
• Design, synthesis and evaluation of novel 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-2-indenyl-3,4-substituted phenyl methanone analogues
  作者：Mohamed Ashraf Ali、Mohammad Shahar Yar、Mohamed Zaheen Hasan、Mohamed Jawed Ahsan、Suresh Pandian

  DOI：10.1016/j.bmcl.2009.07.042

  日期：2009.9

  In present investigation, a series of substituted phenyl-5,6-dimethoxy-1-oxo-2,3-dihydro-1H-2-indenylmethanone analogues were synthesized and were tested for their potential for treating AD disease. All the newly synthesized compounds were showing moderate to high AChE inhibitory activities, with compound 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-2-indenyl-3,4,5-trimethoxyphenylmethanone (5f) produced significant activities with 2.7 +/- 0.01 mu mol/L. (C) 2009 Elsevier Ltd. All rights reserved.
• Discovery of novel antitubercular 3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide/carbothioamide analogues
  作者：Mohamed Jawed Ahsan、Jeyabalan Govinda Samy、Savita Soni、Naresh Jain、Lalit Kumar、Lalit K. Sharma、Hemant Yadav、Lokesh Saini、Rajput Gopal Kalyansing、Narendra S. Devenda、Ravindra Prasad、Chandra Bhushan Jain

  DOI：10.1016/j.bmcl.2011.07.035

  日期：2011.9

  In the present investigation, a series of 3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide/carbothioamide analogues were synthesized and were evaluated for antitubercular activity by two fold serial dilution technique. All the newly synthesized compounds showed low to high inhibitory activities against Mycobacterium tuberculosis H(37)Rv and INH resistant M. tuberculosis. The compound 3-(4-fluorophenyl)-6,7-dimethoxy-3a, 4-dihydro-3H-indeno[1,2-c]pyrazole-2-carbothioamide (4o) was found to be the most promising compound active against M. tuberculosis H(37)Rv and isoniazid resistant M. tuberculosis with minimum inhibitory concentration 3.12 mu M and 6.25 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.