3-(prop-2-yn-1-yl)thiazolidine-2,4-dione | 39137-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-(prop-2-yn-1-yl)thiazolidine-2,4-dione
• 英文别名: 3-(Prop-2-yn-1-yl)-1,3-thiazolidine-2,4-dione；3-prop-2-ynyl-1,3-thiazolidine-2,4-dione
• CAS: 39137-29-6
• 化学式: C₆H₅NO₂S
• mdl: MFCD04319131
• 分子量: 155.177
• InChiKey: AGUSZZRAQMEXDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  248.7±42.0 °C(Predicted)
• 密度：
  1.409±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(prop-2-yn-1-yl)thiazolidine-2,4-dione 在 哌啶 、 铜 、 copper(II) sulfate 、 溶剂黄146 作用下， 以 水 、 叔丁醇 为溶剂， 生成 (E)-3-((1-(3-(((4aR,6R,6aS,9S,11S,11aS,11bS,12S,14R)-11,14-dihydroxy-4,4-dimethyl-8-methylene-7-oxododecahydro-1H-6,11b-(epoxymethano)-6a,9-methanocyclohepta[a]naphthalen-12-yl)ethoxy)propyl)-1H-1,2,3-triazol-4-yl)methyl)-5-ethylidenethiazolidine-2,4-dione
  参考文献：
  名称：

  新型济源冬凌草甲素A-1,2,3-三唑-唑衍生物的合成及生物学评价

  摘要：

  作为我们继续研究有效和潜在安全的抗增殖剂的研究的延续，我们设计，合成了两种新型的济源冬凌草甲素A-1,2,3-三唑-唑杂种，并评估了它们对四种选择的抗增殖活性。癌细胞系（MGC-803，MCF-7，PC-3，Eca-109）。选择了一些具有更好生长抑制作用的化合物，以便在A549和SMMC-7721中进行进一步的研究。大多数合成的化合物对所选的所有癌细胞系均表现出中等至良好的活性。特别地，最具活性的试剂8b显示出对人癌细胞的高效力，IC 50为0.2±0.0至5.0±0.9μM。细胞机理研究阐明了化合物8b在GMC期阻止细胞周期并在SMMC-7721细胞中诱导强烈的凋亡反应。此外，8b可能通过Wnt信号通路抑制SMMC-7721细胞中的集落形成和迁移。由于所有这些原因，化合物8b具有作为抗增殖剂的有希望的潜力。

  DOI：

  10.1016/j.ejmech.2018.08.056
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 3-溴丙炔 在 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 4.0h， 以89%的产率得到3-(prop-2-yn-1-yl)thiazolidine-2,4-dione
  参考文献：
  名称：

  通过铜催化叠氮化物-炔烃环加成分析吡啶基乙烯基喹啉化学空间，发现速效双阶段抗疟药

  摘要：

  为了鉴定速效、多级抗疟药，通过 CuAAC 合成了一系列吡啶基乙烯基喹啉-三唑类似物。大多数化合物在低亚微摩尔浓度下对抗药性疟疾 Dd2 菌株显示出显着的抑制作用。在测试的类似物中，化合物60是最有效的分子，其 EC 50值为 0.04 ± 0.01 μM。我们目前的研究表明，化合物60是一种速效抗疟化合物，它在恶性疟原虫无性生命周期的滋养体阶段表现出阶段特异性作用。此外，化合物60对早期和晚期恶性疟原虫均有活性配子体。从机理的角度来看，化合物60作为 β-血红素形成的抑制剂显示出良好的活性。总的来说，我们的研究结果表明，速效剂60以疟原虫的双重生命阶段为目标，值得进一步研究吡啶基乙烯基喹啉杂种作为新的抗疟药。

  DOI：

  10.1016/j.ejmech.2020.112889

文献信息

• Diversity-oriented synthesis of spirothiazolidinediones and their biological evaluation
  作者：Sambasivarao Kotha、Gaddamedi Sreevani、Lilya U Dzhemileva、Milyausha M Yunusbaeva、Usein M Dzhemilev、Vladimir A D’yakonov

  DOI：10.3762/bjoc.15.269

  日期：——

  We report a new synthetic approach to assemble spirothiazolidinediones via a [2 + 2 + 2] cyclotrimerization reaction and the derivatives were further functionalized through DA chemistry and click reaction. Using flow cytometry, it was shown for the first time that the new benzyl alcohol derivatives of thiazolidine-2,4-dione generated here are efficient apoptosis inducers in the HeLa, Hek293, U937,

  我们报告了一种新的合成方法，可通过[2 + 2 + 2]环三聚反应组装螺噻唑烷二酮，并通过DA化学和点击反应进一步将衍生物官能化。使用流式细胞仪首次证明，此处生成的新的噻唑烷-2,4-二酮苄醇衍生物是HeLa，Hek293，U937，Jurkat和K562细胞系中有效的凋亡诱导剂。
• Dual inhibitors of the dengue and West Nile virus NS2B–NS3 proteases: Synthesis, biological evaluation and docking studies of novel peptide-hybrids
  作者：Allan Bastos Lima、Mira A.M. Behnam、Yasmin El Sherif、Christoph Nitsche、Sergio M. Vechi、Christian D. Klein

  DOI：10.1016/j.bmc.2015.07.012

  日期：2015.9

  Dengue virus (DENV) and West Nile virus (WNV) are mosquito-borne arboviruses responsible for causing acute systemic diseases and severe health conditions in humans. The discovery of therapies capable to prevent infections or treat infected individuals remains an important challenge, since no vaccine or specific efficient treatment could be developed so far. In this context, we present herein the synthesis

  登革热病毒（DENV）和西尼罗河病毒（WNV）是蚊子传播的虫媒病毒，负责引起人类的急性系统性疾病和严重的健康状况。由于迄今为止尚未开发出疫苗或特定的有效疗法，因此发现能够预防感染或治疗受感染个体的疗法仍然是一项重要的挑战。在此背景下，我们在此介绍基于含有非极性基团的2,4-噻唑烷二酮骨架的新型肽杂交体的合成，表征，生物学评估和对接研究。最有前途的化合物的IC 500.75μM的抗WNV蛋白酶活性，与我们先前报道的化合物相比，活性提高了70倍。实验结果和对接研究与以下假设一致：支架中的非极性基团对于获得抑制剂与DENV和WNV NS2B–NS3丝氨酸蛋白酶的底物识别区域中的疏水口袋之间的相互作用很重要。
• Structural exploration, synthesis and pharmacological evaluation of novel 5-benzylidenethiazolidine-2,4-dione derivatives as iNOS inhibitors against inflammatory diseases
  作者：Liang Ma、Heying Pei、Lei Lei、Linhong He、Jinying Chen、Xiaolin Liang、Aihua Peng、Haoyu Ye、Mingli Xiang、Lijuan Chen

  DOI：10.1016/j.ejmech.2014.12.036

  日期：2015.3

  In our previous work, 3I inhibited the LPS-induced iNOS activity and NO production in RAW 264.7 cells and improved joint inflammation and cartilage destruction in inflammatory model. In this study, we synthesized 59 derivatives and bioisosteres on the basis of 3I by Knoevenagel condensation and biologically evaluated for the study of structure-activity relationship (SAR). We found that 7-44 suppressed the iNOS activity (IC50 25.2 mu M) and LPS-induced NO production (IC50 45.6 mu M) in RAW 264.7 cells. As for the SAR study, the dimethoxylphenyl group of 7-44 was potential for a further modification. At a dose of 10 mg/kg, oral administration of 7-44 possessed protective properties in both carrageenan-induced paw edema of male ICR mice and adjuvant-induced arthritis of Lewis female rats. Although the activity of 7-44 was slightly inferior, the PK profiles of 7-44 were superior to those of 3I. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Site-Specific Chemical Modification of Peptide and Protein by Thiazolidinediones
  作者：Peng Wang、Shumei Zhang、Qiuyue Meng、Ying Liu、Luqing Shang、Zheng Yin

  DOI：10.1021/acs.orglett.5b00005

  日期：2015.3.20

  A direct aldol reaction employing 2,4-thiazolidinediones as nucleophilic donors was performed to modify peptides and protein under mild conditions. Various functional groups could be readily introduced into protein without conformation change.
• Design, synthesis, and cytotoxic activities of novel hybrids of parthenolide and thiazolidinedione via click chemistry
  作者：Jie Qiu、Chun-Mao Yuan、Min Wen、Ya-Nan Li、Juan Chen、Jun-You Jian、Lie-Jun Huang、Wei Gu、Yan-Mei Li、Xiao-Jiang Hao

  DOI：10.1080/10286020.2019.1597055

  日期：2020.5.3

  A series of novel parthenolide-thiazolidinedione hybrids have been synthesized via a click chemistry-mediated coupling between parthenolide and thiazolidinedione, and evaluated for their cytotoxic activities. The results indicated that all the hybrids showed moderate cytotoxic effects on human cancer cell lines, including human erythroleukemia cell line (HEL), prostate (PC3), and breast (MDA-MB-231) by MTT assay. In particular, compound VI-6 exhibited the best cytotoxic activities against the MDA-MB-231 cells with IC50 value of 2.07 mu M, which was about eight times more active than that of the original compound (PTL). These interesting results might be used to develop novel lead scaffolds for potential anticancer agents.[GRAPHICS].