2-硫氧代-3-[4-(三氟甲基)苯基]-1,3-噻唑啉-4-酮 | 57669-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-硫氧代-3-[4-(三氟甲基)苯基]-1,3-噻唑啉-4-酮
• 英文名称: 2-thioxo-3-(4-(trifluoromethyl)phenyl)thiazolidin-4-one
• 英文别名: 2-Thioxo-3-[4-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one；2-sulfanylidene-3-[4-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one
• CAS: 57669-54-2
• 化学式: C₁₀H₆F₃NOS₂
• mdl: MFCD03184514
• 分子量: 277.291
• InChiKey: AJEXEUDSGYIZHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-羧基苯甲醛 、 2-硫氧代-3-[4-(三氟甲基)苯基]-1,3-噻唑啉-4-酮 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 3-((4-oxo-2-thioxo-3-(4-(trifluoromethyl)phenyl)thiazolidin-5-ylidene)methyl)benzoic acid
  参考文献：
  名称：

  Thiazolidinone CFTR inhibitors with improved water solubility identified by structure–activity analysis

  摘要：

  The thiazolidinone 3-[(3-trifluoromethyl)phenyl]-5-[(4-carboxyphenyl)methylene]-2-thioxo-4-thiazolidinone (CFTRinh-172) inhibits cystic fibrosis transmembrane conductance regulator ( CFTR) chloride channel conductance with submicromolar affinity and blocks cholera toxin-induced intestinal fluid secretion. Fifty-eight CFTRinh-172 analogs were synthesized to identify CFTR inhibitors with improved water solubility, exploring modi. cations in its two phenyl rings, thiazolidinone core, and core-phenyl connectors. Greatest CFTR inhibition potency was found for 3-CF3 and polar group-substituted-phenyl rings, and a thiazolidinone core. Two compounds with similar to 1 mu M CFTR inhibition potency and solubility >180 mu M(>10-fold more than CFTRinh-172) were identified: Tetrazolo-172, containing 4-tetrazolophenyl in place of 4-carboxyphenyl, and Oxo-172, containing thiazolidinedione in place of the thiazolidinone core. These water soluble thiazolidinone analogs had low cellular toxicity. The improved water solubility of Tetrazolo- and Oxo-172 make them potential lead candidates for therapy of secretory diarrheas and polycystic kidney disease. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.044
• 作为产物：
  描述：

  1,4-diazabicyclo[2.2.2]octane (4-(trifluoromethyl)phenyl)carbamodithioate 在 三光气 、 三乙胺 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 生成 2-硫氧代-3-[4-(三氟甲基)苯基]-1,3-噻唑啉-4-酮
  参考文献：
  名称：

  4-噻唑烷酮衍生物作为人二氢乳清酸酯脱氢酶的新型抑制剂的合成，构效关系和结合模式分析

  摘要：

  合成了一系列的4-噻唑烷酮衍生物，并作为新型人二氢乳清酸脱氢酶（h DHODH）抑制剂进行了评估。化合物26和31的IC 50值分别为1.75和1.12μM。构效关系进行了总结。进一步的结合模式分析表明，化合物31可以与Tyr38形成氢键，并与Ala55形成水介导的氢键，这对于维持该系列化合物的生物活性可能是必需的。R上苯基对位或间位的进一步结构优化将导致鉴定更有效的hDHODH抑制剂。

  DOI：

  10.1039/c7md00081b

文献信息

• Design, synthesis and biological evaluation of 3-substituted 2,5-dimethyl-N-(3-(1H-tetrazol-5-yl)phenyl)pyrroles as novel potential HIV-1 gp41 inhibitors
  作者：Xiao-Yang He、Peng Zou、Jiayin Qiu、Ling Hou、Shibo Jiang、Shuwen Liu、Lan Xie

  DOI：10.1016/j.bmc.2011.09.047

  日期：2011.11

  Based on the structure of HIV-1 gp41 binding site for small-molecule inhibitors, optimization of lead 2 resulted in the discovery of a new series of 2,5-dimethyl-3-(5-(N-phenylrhodaninyl)methylene)-N-(3-(1H-tetrazol-5-yl)phenyl)pyrrole compounds with improved anti-HIV-1 activity. The most active compounds 13a and 13j exhibited significant potency against gp41 6-HB formation with IC50 values of 4.4

  基于HIV-1 gp41的结合位点的结构为小分子抑制剂，铅优化2产生了一系列新的2,5-的发现-二甲基-3-（5-（Ñ -phenylrhodaninyl）亚甲基）- ñ -具有改善的抗HIV-1活性的（3-（1H-四唑-5-基）苯基）吡咯化合物。活性最高的化合物13a和13j对gp41 6-HB的形成具有显着的效力，IC 50值为4.4和4.6μM，对HIV-1在MT-2细胞中的EC-1复制具有EC 50 值分别为3.2和2.2μM，从而为开发靶向gp41的高效小分子HIV融合抑制剂提供了新的起点。
• Synthesis and biological activity evaluation of new thiazolidinone-diclofenac hybrid molecules
  作者：Yulia Shepeta、Andrii Lozynskyi、Marta Sulyma、Ihor Nektegayev、Philippe Grellier、Roman Lesyk

  DOI：10.1080/10426507.2020.1759060

  日期：2020.10.2

  LCMS spectroscopic data. Target compounds were screened for their in vitro anticancer activity according to US NCI protocols, in vitro trypanocidal activity toward Trypanosoma brucei brucei (Tbb) and evaluated for anti-inflammatory activity on the carrageenan edema model in rats. Biological screening data led to identification of compounds 3.3 ([2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid N`-(4

  摘要 设计并合成了一系列新型[2-(2,6-二氯苯基氨基)-苯基]-乙酸N`-3-(取代)-4-噻唑烷-5-亚基甲基-酰肼衍生物。合成化合物的结构由其 1H NMR、13C NMR 和 LCMS 光谱数据证实。根据美国 NCI 协议筛选目标化合物的体外抗癌活性、对布氏锥虫 (Tbb) 的体外杀锥虫活性，并评估对大鼠角叉菜胶水肿模型的抗炎活性。生物筛选数据导致鉴定了化合物 3.3（[2-(2,6-二氯-苯基氨基)-苯基]-乙酸 N`-(4-oxo-2-thioxo-thiazolidin-5-ylidenemethyl)-hydrazide）和3.7 ([2-(2, 6-二氯-苯氨基)-苯基]-乙酸 N`-(4-oxo-2-thioxo-3-(3-trifluoromethylphenyl)thiazolidin-5-ylidenemethyl)-hydrazide) -细胞肺癌 NCI-H522
• Synthesis, Characterization, Antibacterial and Antioxidant Potency of NSubstituted- 2-Sulfanylidene-1,3-Thiazolidin-4-one Derivatives and QSAR Study
  作者：Harshad Brahmbhatt、Maja Molnar、Valentina Pavić、Vesna Rastija

  DOI：10.2174/1573406415666181205163052

  日期：2019.11.18

  these key building blocks. The objective was to synthesize a series of rhodanine derivatives and to investigate their antimicrobial and antioxidant activity. Also, in order to obtain an insight into their structure-activity relationship, QSAR studies on the antioxidant activity were performed. Methods: 1H and 13C FTNMR spectra were recorded on Bruker Avance 600 MHz NMR Spectrometer, mass analysis was

  背景：罗丹宁因其在药物化学中的潜在作用和重要作用而闻名，因为其衍生物具有广泛的药理活性，例如抗菌，抗真菌，抗糖尿病，抗结核，抗HIV，抗寄生虫，抗氧化剂，抗癌，抗增殖和驱虫药。 目标：由于N-取代的若丹宁合成子很少可商购，因此需要开发一种简单的合成方法来合成这些关键构件。目的是合成一系列若丹宁衍生物，并研究其抗菌和抗氧化活性。另外，为了深入了解它们的结构活性关系，进行了抗氧化活性的QSAR研究。 方法：在Bruker Avance 600 MHz NMR光谱仪上记录1H和13C FTNMR光谱，并通过LC-MS / MS API 2000在ESI +模式下进行质量分析。2,2-二苯基-1-吡啶并肼基自由基清除活性（％DPPH）在二甲基亚砜（DMSO）中作为溶剂测定。通过改良的肉汤微量稀释法，以最低抑菌浓度（MICs）评估了对枯草芽孢杆菌，金黄色葡萄球菌（革兰氏阳性）和大肠杆菌，铜绿假单胞菌（革兰氏阴性）细菌的抗菌活性。
• Cystic fibrosis transmembrane conductance regulator protein inhibitors and uses thereof
  申请人：——

  公开号：US20040235800A1

  公开（公告）日：2004-11-25

  The invention provides compositions, pharmaceutical preparations and methods for inhibition of cystic fibrosis transmembrane conductance regulator protein (CFTR) that are useful for the study and treatment of CFTR-mediated diseases and conditions. The compositions and pharmaceutical preparations of the invention may comprise one or more thiazolidinone compounds, and may additionally comprise one or more pharmaceutically acceptable carriers, excipients and/or adjuvants. The methods of the invention comprise, in certain embodiments, administering to a patient suffering from a CFTR-mediated disease or condition, an efficacious amount of a thiazolidinone compound. In other embodiments the invention provides methods of inhibiting CFTR that comprise contacting cells in a subject with an effective amount of a thiazolidinone compound. In addition, the invention features a non-human animal model of CFTR-mediated disease which model is produced by administration of a thiazolidinone compound to a non-human animal in an amount sufficient to inhibit CFTR.

  本发明提供了用于抑制囊性纤维化跨膜传导调节蛋白（CFTR）的组合物、制药制剂和方法，这些组合物、制药制剂和方法对于研究和治疗CFTR介导的疾病和病况非常有用。本发明的组合物和制药制剂可以包括一种或多种噻唑烷酮化合物，并且可以另外包括一种或多种药学上可接受的载体、赋形剂和/或佐剂。本发明的方法包括，在某些实施例中，向患有CFTR介导的疾病或病况的患者施用有效量的噻唑烷酮化合物。在其他实施例中，本发明提供了抑制CFTR的方法，包括用有效量的噻唑烷酮化合物接触受体内细胞。此外，本发明还提供了一种CFTR介导的疾病的非人类动物模型，该模型通过向非人类动物施用足以抑制CFTR的噻唑烷酮化合物产生。
• CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR PROTEIN INHIBITORS AND USES THEREOF
  申请人：Verkman Alan

  公开号：US20080064666A1

  公开（公告）日：2008-03-13

  The invention provides compositions, pharmaceutical preparations and methods for inhibition of cystic fibrosis transmembrane conductance regulator protein (CFTR) that are useful for the study and treatment of CFTR-mediated diseases and conditions. The compositions and pharmaceutical preparations of the invention may comprise one or more thiazolidinone compounds, and may additionally comprise one or more pharmaceutically acceptable carriers, excipients and/or adjuvants. The methods of the invention comprise, in certain embodiments, administering to a patient suffering from a CFTR-mediated disease or condition, an efficacious amount of a thiazolidinone compound. In other embodiments the invention provides methods of inhibiting CFTR that comprise contacting cells in a subject with an effective amount of a thiazolidinone compound. In addition, the invention features a non-human animal model of CFTR-mediated disease which model is produced by administration of a thiazolidinone compound to a non-human animal in an amount sufficient to inhibit CFTR.

  本发明提供了抑制囊性纤维化跨膜传导调节蛋白（CFTR）的组合物、药物制剂和方法，这些组合物、药物制剂和方法对于研究和治疗CFTR介导的疾病和病况非常有用。本发明的组合物和药物制剂可以包括一个或多个噻唑烷酮化合物，并且可以另外包括一个或多个药用载体、辅料和/或佐剂。本发明的方法包括，在某些实施例中，向患有CFTR介导的疾病或病况的患者施用有效量的噻唑烷酮化合物。在其他实施例中，本发明提供了抑制CFTR的方法，包括用有效量的噻唑烷酮化合物接触患者细胞。此外，本发明还提供了一种CFTR介导的疾病的非人类动物模型，该模型通过向非人类动物施用足以抑制CFTR的噻唑烷酮化合物而产生。