5-(1-benzyl-1H-indol-3-ylmethylene)-thiazolidine-2,4-dione | 192996-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-(1-benzyl-1H-indol-3-ylmethylene)-thiazolidine-2,4-dione
• 英文别名: 5-[(1-Benzylindol-3-yl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 192996-35-3
• 化学式: C₁₉H₁₄N₂O₂S
• 分子量: 334.398
• InChiKey: FSHJJYQZCGYBSK-UHFFFAOYSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  76.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(1-benzyl-1H-indol-3-ylmethylene)-thiazolidine-2,4-dione 、 硫酸二甲酯 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到5-[(1-Benzylindol-3-yl)methylidene]-3-methyl-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  L-Proline-Catalyzed Synthesis of Novel 5-(1H-Indol-3-yl-methylene)-thiazolidine-2,4-dione Derivatives as Potential Antihyperglycemic Agents

  摘要：

  Knoevenagel condensation between indole-3-aldehyde 1 and an active methylene group containing 2,4-thiazolidinedione 2 in refluxing toluene using L-proline as a catalyst yielded 3, which on alkylation using 2 equivalents of alkylating agent under phase-transfer-catalyzed (PTC) conditions using K2CO3 as a base in dimethylformamide gave N,N-I-symmetrically disubstituted 5-(1H-indol-3ylmethylene)-thiazolidine-2,4-diones 4. Alternately, 4 can be synthesized by condensing 5 and 6 in a single step. Using this synthetic strategy, N,N-I-unsymmetricallydisubstituted derivatives 9a-f were prepared either by condensing 6 with N-substituted-2,4-thiazolidinedione 5 to obtain 7 followed by alkylation under PTC conditions or condensing 6 with N-unsubstituted-2,4-thiazolidinedione 2 to yield 8 followed by alkylation under PTC conditions. The latter are the dehydro analogs of the dihydro-N-substituted-5-(1H-indol-3-yl-methylene)-thiazolidine-2,4-diones, which are potential antihyperglycemic agents.

  DOI：

  10.1080/00397911.2010.515352
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 1-苄基吲哚-3-甲醛 在 溶剂黄146 、 β-丙氨酸 作用下， 反应 4.0h， 生成 5-(1-benzyl-1H-indol-3-ylmethylene)-thiazolidine-2,4-dione
  参考文献：
  名称：

  新型聚（ADP-核糖）聚合酶（PARP-1）抑制剂的基于结构的设计。

  摘要：

  聚（ADP-核糖）聚合酶（PARP-1）是一种成熟的核蛋白，在信号传导和DNA修复中具有突出作用。已经鉴定出多种临床候选物与PARP-1抑制有关。基于先前研究确定的药效学特征和分子对接相互作用，已对噻唑烷-2,4-二酮衍生物的PARP抑制活性进行了评估。通过体外试验，确定了5-（（1-（4-异丙基苄基）-1H-吲哚-3-基）亚甲基）噻唑烷-2,4-二酮（16）是一种具有低微摩尔抑制活性的有效抑制剂。 （（（\ hbox {IC} _ {50} \，{=} \，0.74 \，\ pm \，0.25 \，\ upmu \ hbox {M}）\）。因此，在本研究中使用的基于结构的设计方法有助于确定噻唑烷-2,4-二酮是针对PARP-1的新型支架，以开发有效的抗癌药物。

  DOI：

  10.1007/s11030-017-9754-7

文献信息

• Novel, Recyclable, and Thermally Stable Task-Specific Ionic Liquid (TBA Acetate) Medium/Catalyst for the Synthesis of Indolylidinecyclic-1,3- and -1,4-diketones
  作者：Sd. Riyaz、A. Indrasena、A. Naidu、P. Dubey

  DOI：10.1080/00397911.2013.806988

  日期：2014.2

  A simple and efficient synthesis of indolylidinethiazolidnediones (3) and indolylidinecyclic-1,3-diketones (5) has been developed by reaction of indole-3-aldehyde (1) with thiazolidinedione (2) or cyclic-1,3-diketones (4) using tetra butyl ammonium acetate (TBAA) melt as novel, cost-effective, and recyclable ionic liquid under solvent-free green conditions at 100 degrees C for 15-20min without additional use of catalyst. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
• L-Proline-Catalyzed Synthesis of Novel 5-(1H-Indol-3-yl-methylene)-thiazolidine-2,4-dione Derivatives as Potential Antihyperglycemic Agents
  作者：S. Riyaz、A. Naidu、P. K. Dubey

  DOI：10.1080/00397911.2010.515352

  日期：2011.9.15

  Knoevenagel condensation between indole-3-aldehyde 1 and an active methylene group containing 2,4-thiazolidinedione 2 in refluxing toluene using L-proline as a catalyst yielded 3, which on alkylation using 2 equivalents of alkylating agent under phase-transfer-catalyzed (PTC) conditions using K2CO3 as a base in dimethylformamide gave N,N-I-symmetrically disubstituted 5-(1H-indol-3ylmethylene)-thiazolidine-2,4-diones 4. Alternately, 4 can be synthesized by condensing 5 and 6 in a single step. Using this synthetic strategy, N,N-I-unsymmetricallydisubstituted derivatives 9a-f were prepared either by condensing 6 with N-substituted-2,4-thiazolidinedione 5 to obtain 7 followed by alkylation under PTC conditions or condensing 6 with N-unsubstituted-2,4-thiazolidinedione 2 to yield 8 followed by alkylation under PTC conditions. The latter are the dehydro analogs of the dihydro-N-substituted-5-(1H-indol-3-yl-methylene)-thiazolidine-2,4-diones, which are potential antihyperglycemic agents.
• Structure-based design of new poly (ADP-ribose) polymerase (PARP-1) inhibitors
  作者：Navriti Chadha、Ameteshar Singh Jaggi、Om Silakari

  DOI：10.1007/s11030-017-9754-7

  日期：2017.8

  identified from previous studies and molecular docking interactions, thiazolidine-2,4-dione derivatives have been evaluated for their PARP inhibitory activity. From an in vitro assay, 5-((1-(4-isopropylbenzyl)-1H-indol-3-yl)methylene)thiazolidine-2,4-dione (16) was identified as a potent inhibitor having low micromolar inhibitory activity \((\hbox IC}_50} \,=}\, 0.74 \,\pm \, 0.25\,\upmu \hbox M})\)

  聚（ADP-核糖）聚合酶（PARP-1）是一种成熟的核蛋白，在信号传导和DNA修复中具有突出作用。已经鉴定出多种临床候选物与PARP-1抑制有关。基于先前研究确定的药效学特征和分子对接相互作用，已对噻唑烷-2,4-二酮衍生物的PARP抑制活性进行了评估。通过体外试验，确定了5-（（1-（4-异丙基苄基）-1H-吲哚-3-基）亚甲基）噻唑烷-2,4-二酮（16）是一种具有低微摩尔抑制活性的有效抑制剂。 （（（\ hbox IC} _ 50} \，=} \，0.74 \，\ pm \，0.25 \，\ upmu \ hbox M}）\）。因此，在本研究中使用的基于结构的设计方法有助于确定噻唑烷-2,4-二酮是针对PARP-1的新型支架，以开发有效的抗癌药物。