2,4-噻唑烷二酮,5-(1H-吲哚-3-基亚甲基)- | 188713-12-4

• 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
• 中文名称: 2,4-噻唑烷二酮,5-(1H-吲哚-3-基亚甲基)-
• 英文名称: 5-(1H-indol-3-ylmethylene)-thiazolidine-2,4-dione
• 英文别名: 5-(1H-indol-3-ylmethylidene)-1,3-thiazolidine-2,4-dione
• CAS: 188713-12-4
• 化学式: C₁₂H₈N₂O₂S
• 分子量: 244.274
• InChiKey: YRPCEGFPKMQCHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.96
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,4-噻唑烷二酮,5-(1H-吲哚-3-基亚甲基)- 在 水 、 sodium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以56 %的产率得到5-Skatylthiazolidin-2,4-dion
  参考文献：
  名称：

  5-亚苄基噻唑烷-2,4-二酮的电化学还原：制备格列酮 API 的绿色方法

  摘要：

  描述了一种用于化学选择性还原亚苄基噻唑烷-2,4-二酮和类似杂环的无过渡金属方法，允许以高达 90% 的收率制备各种相应的还原衍生物。该协议具有简单且安全的实验装置，其中用水作为氢源。为了进一步证明这种转化的合成效用，制备了抗糖尿病 API 吡格列酮，收率为 81%。据我们所知，这是第一个用于合成吡格列酮的无氢化物和过渡金属的方案，突显了其在学术和工业合成中作为更绿色替代品的潜在用途。

  DOI：

  10.1039/d3cc02363j
• 作为产物：
  描述：

  2,4-噻唑烷二酮 在 吗啉 、 3-吲哚甲醛 作用下， 以 乙醇 为溶剂， 反应 1.17h， 以53.64%的产率得到2,4-噻唑烷二酮,5-(1H-吲哚-3-基亚甲基)-
  参考文献：
  名称：

  新型吲哚衍生物作为有前途的DNA结合剂的合成以及抗肿瘤和抗拓扑异构酶I活性的评估

  摘要：

  带有吲哚核的分子具有多种生物学特性，例如抗肿瘤和抗炎活性，可以与DNA和蛋白质的相互作用相关。这项研究的重点是合成带有噻唑烷和咪唑烷环缩合成侧链的新吲哚衍生物，并评估它们与DNA相互作用的能力以及抗肿瘤和拓扑异构酶的抑制活性。已成功合成所有衍生物，并通过质谱（MS），红外（IR），光谱1 H NMR，13 C NMR，COZY 1 H- 1 H和HSQC 1 H- 13阐明了它们的结构C.使用抗增殖MTT测定法评估了针对不同癌细胞系的抗肿瘤活性。使用溴化乙锭（EB）作为荧光探针，通过吸收光谱法和荧光技术分析DNA结合能力。在与ctDNA（小牛胸腺DNA）相互作用后，除了光谱最大值的蓝移或红移以外，还观察到了化合物的光谱性质发生了变化，具有低变色和增色作用。吲哚衍生物5-（1 H-吲哚-3-基亚甲基）-噻唑烷-2,4-二酮（4c）在针对所测乳腺线（T47D）的抗肿瘤试验中表现出最佳结果，IC

  DOI：

  10.1016/j.ejmech.2017.05.012

文献信息

• Stereoselective synthesis of spirocyclic pyrrolidines/pyrrolizidines/pyrrolothiazolidines using <scp>l</scp>-proline functionalized manganese ferrite nanorods as a novel heterogeneous catalyst
  作者：Malihe Akhavan、Ahmadreza Bekhradnia

  DOI：10.1039/d1ra00841b

  日期：——

  three-component protocol has been reported for the stereoselective synthesis of a new class of spiro thiazolidines. A series of spiro-heterocycle derivatives were produced stereoselectively in high yields by the reaction of 5-arylidene thiazolidine-2,4-diones, isatin, and secondary amino acids in the presence of MnCoCuFe2O4@L-proline (MCCFe2O4@L-proline) magnetic nanorods as a novel nanocatalyst. The synthesized

  已经报道了一种高效、绿色、一锅法和三组分的方案，用于立体选择性合成一类新的螺噻唑烷。通过 5-亚芳基噻唑烷-2,4-二酮、靛红和仲氨基酸在 MnCoCuFe 2 O 4 @ L-脯氨酸 (MCCFe 2 O 4 @ L-脯氨酸）磁性纳米棒作为一种新型纳米催化剂。合成的催化剂通过多种技术充分表征了热稳定性、磁性和其他物理化学性质。它被用作一种高效且可重复使用的催化剂，用于合成高产率的螺环吡咯烷/吡咯里西啶/吡咯噻唑烷衍生物的内向异构体。这些杂环螺化合物的区域选择性和立体化学通过1 H、13 C、HMBC、HSQC 和 COZY NMR 光谱技术确定。所提出的协议的主要吸引人的特点是高产率、高水平的非对映选择性和催化剂易于回收而不会显着丧失其催化活性。
• Indole and 2,4-Thiazolidinedione conjugates as potential anticancer modulators
  作者：Domenica M. Corigliano、Riyaz Syed、Sebastiano Messineo、Antonio Lupia、Rahul Patel、Chittireddy Venkata Ramana Reddy、Pramod K. Dubey、Carmela Colica、Rosario Amato、Giovambattista De Sarro、Stefano Alcaro、Adisherla Indrasena、Antonio Brunetti

  DOI：10.7717/peerj.5386

  日期：——

  Thiazolidinediones (TZDs), also called glitazones, are five-membered carbon ring molecules commonly used for the management of insulin resistance and type 2 diabetes. Recently, many prospective studies have also documented the impact of these compounds as anti-proliferative agents, though several negative side effects such as hepatotoxicity, water retention and cardiac issues have been reported. In this work, we synthesized twenty-six new TZD analogues where the thiazolidinone moiety is directly connected to an N-heterocyclic ring in order to lower their toxic effects.

  By adopting a widely applicable synthetic method, twenty-six TZD derivatives were synthesized and tested for their antiproliferative activity in MTT and Wound healing assays with PC3 (prostate cancer) and MCF-7 (breast cancer) cells.

  Three compounds, out of twenty-six, significantly decreased cellular viability and migration, and these effects were even more pronounced when compared with rosiglitazone, a well-known member of the TZD class of antidiabetic agents. As revealed by Western blot analysis, part of this antiproliferative effect was supported by apoptosis studies evaluating BCL-xL and C-PARP protein expression.

  Our data highlight the promising potential of these TZD derivatives as anti-proliferative agents for the treatment of prostate and breast cancer.

  吡唑二酮类药物（TZDs），也称为格列酮，是常用于管理胰岛素抵抗和2型糖尿病的五元碳环分子。最近，许多前瞻性研究还记录了这些化合物作为抗增殖剂的影响，尽管已报告了一些负面副作用，如肝毒性、水潴留和心脏问题。在这项工作中，我们合成了二十六种新的TZD类似物，其中噻唑烷酮基团直接连接到N-杂环环，以降低其毒性作用。 通过采用一种广泛适用的合成方法，合成了二十六种TZD衍生物，并在MTT和伤口愈合实验中测试它们对PC3（前列腺癌）和MCF-7（乳腺癌）细胞的抗增殖活性。 在二十六种化合物中，有三种显著降低了细胞的存活率和迁移率，与罗格列酮（TZD类抗糖尿病药物的知名成员）相比，这些效应甚至更加显著。根据Western blot分析，部分这种抗增殖效应得到了通过评估BCL-xL和C-PARP蛋白表达的凋亡研究的支持。 我们的数据突显了这些TZD衍生物作为治疗前列腺癌和乳腺癌的抗增殖剂的潜在前景。
• 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.
• 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.]
• Synthesis of novel indole derivatives as promising DNA-binding agents and evaluation of antitumor and antitopoisomerase I activities
  作者：Elizabeth Almeida Lafayette、Sinara Mônica Vitalino de Almeida、Renata Virginia Cavalcanti Santos、Jamerson Ferreira de Oliveira、Cezar Augusto da Cruz Amorim、Rosali Maria Ferreira da Silva、Maira Galdino da Rocha Pitta、Ivan da Rocha Pitta、Ricardo Olimpio de Moura、Luiz Bezerra de Carvalho Júnior、Moacyr Jesus Barreto de Melo Rêgo、Maria do Carmo Alves de Lima

  DOI：10.1016/j.ejmech.2017.05.012

  日期：2017.8

  Molecules bearing indole nucleus present diverse biological properties such as antitumor and anti-inflammatory activities that can be associated both to DNA and protein interactions. This study focused on the synthesis of new indole derivatives with thiazolidines and imidazolidine rings condensed as side chains as well as the evaluation of their ability to interact with the DNA and antitumor and topoisomerase

  带有吲哚核的分子具有多种生物学特性，例如抗肿瘤和抗炎活性，可以与DNA和蛋白质的相互作用相关。这项研究的重点是合成带有噻唑烷和咪唑烷环缩合成侧链的新吲哚衍生物，并评估它们与DNA相互作用的能力以及抗肿瘤和拓扑异构酶的抑制活性。已成功合成所有衍生物，并通过质谱（MS），红外（IR），光谱1 H NMR，13 C NMR，COZY 1 H- 1 H和HSQC 1 H- 13阐明了它们的结构C.使用抗增殖MTT测定法评估了针对不同癌细胞系的抗肿瘤活性。使用溴化乙锭（EB）作为荧光探针，通过吸收光谱法和荧光技术分析DNA结合能力。在与ctDNA（小牛胸腺DNA）相互作用后，除了光谱最大值的蓝移或红移以外，还观察到了化合物的光谱性质发生了变化，具有低变色和增色作用。吲哚衍生物5-（1 H-吲哚-3-基亚甲基）-噻唑烷-2,4-二酮（4c）在针对所测乳腺线（T47D）的抗肿瘤试验中表现出最佳结果，IC