4-Thiazolidinone, 2-(2,6-difluorophenyl)-3-(4-methyl-2-pyridinyl)-

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Thiazolidinone, 2-(2,6-difluorophenyl)-3-(4-methyl-2-pyridinyl)-
• 英文别名: 2-(2,6-difluorophenyl)-3-(4-methylpyridin-2-yl)-1,3-thiazolidin-4-one
• 化学式: C₁₅H₁₂F₂N₂OS
• 分子量: 306.336
• InChiKey: NRNTZKJLIWRPHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Thiazolidinone, 2-(2,6-difluorophenyl)-3-(4-methyl-2-pyridinyl)- 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以89%的产率得到2-(2,6-difluorophenyl)-3-(4-methylpyridin-2-yl)-1,3-thiazolidine-4-thione
  参考文献：
  名称：

  Synthesis and anti-HIV activity of 2,3-diaryl-1,3-thiazolidin-4-(thi)one derivatives

  摘要：

  Several 2,3-diaryl-1,3-thiazolidine-4-thione derivatives and 2,3-diaryl-1,3-thiazolidin-4-ones bearing a methyl group at C-5 position have been synthesized and tested as anti-HIV agents, The results of the in vitro tests showed that some of them proved to be effective inhibitors of HIV-1 replication. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01268-5
• 作为产物：
  描述：

  2-氨基-4-甲基吡啶 、 2,6-二氟苯甲醛 、 巯基乙酸 以 甲苯 为溶剂， 反应 20.0h， 生成 4-Thiazolidinone, 2-(2,6-difluorophenyl)-3-(4-methyl-2-pyridinyl)-
  参考文献：
  名称：

  发现2,3-二芳基-1,3-噻唑烷-4-酮是有效的抗HIV-1药物。

  摘要：

  报道了一系列2，3-二芳基-1，3-噻唑烷酮-4-酮的设计，合成和抗HIV活性。一些衍生物被证明在纳摩尔浓度下抑制HIV-1复制非常有效，因此可以作为非核苷HIV-1 RT抑制剂（NNRTIs）。SAR研究表明，噻唑烷酮核的2和3位上的取代基的性质在很大程度上影响了这种新型有效抗病毒剂的体外抗HIV活性。

  DOI：

  10.1016/s0960-894x(01)00304-3

文献信息

• Design, Synthesis, Structure−Activity Relationships, and Molecular Modeling Studies of 2,3-Diaryl-1,3-thiazolidin-4-ones as Potent Anti-HIV Agents
  作者：Maria L. Barreca、Jan Balzarini、Alba Chimirri、Erik De Clercq、Laura De Luca、Hans Dieter Höltje、Monika Höltje、Anna Maria Monforte、Pietro Monforte、Christophe Pannecouque、Angela Rao、Maria Zappalà

  DOI：10.1021/jm020977+

  日期：2002.11.1

  Starting from 1H,3H-thiazolo[3,4-albenzimidazoles (TBZs), we performed the design, synthesis, and the structure-activity relationship studies of a series of 2,3-diaryl-1,3-thiazolidin-4-ones. Some derivatives proved to be highly effective in inhibiting HIV-1 replication at nanomolar concentrations with minimal cytotoxicity, thereby acting as nonnucleoside HIV-1 RT inhibitors (NNRTIs). Computational studies were used to delineate the ligand-RT interactions and to probe the binding of the ligands to HIV-1 RT.
• Anti-HIV agents: design and discovery of new potent RT inhibitors
  作者：Maria Letizia Barreca、Alba Chimirri、Erik De Clercq、Laura De Luca、Anna-Maria Monforte、Pietro Monforte、Angela Rao、Maria Zappalà

  DOI：10.1016/s0014-827x(03)00024-7

  日期：2003.3

  This paper reports our work in the field of nonnucleoside RT inhibitors (NNRTIs). On the basis of extensive studies on 1H,3H-thiazolo[3,4-a]benzimidazole derivatives (TBZs) followed by structure-activity relationship (SAR) considerations and molecular modeling, the design and synthesis of a series of 2,3-diaryl-1,3-thiazolidin-4-ones have been performed. Some derivatives proved to be highly effective in inhibiting human immunodeficiency virus type-1 (HIV-1) replication at nanomolar concentrations with minimal toxicity, acting as reverse transcriptase (RT) inhibitors. Computational studies were used in order to probe the binding of our ligands to HIV-1-RT.
• Discovery of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-HIV-1 agents
  作者：Maria Letizia Barreca、Alba Chimirri、Laura De Luca、Anna-Maria Monforte、Pietro Monforte、Angela Rao、Maria Zappalà、Jan Balzarini、Erik De Clercq、Christophe Pannecouque、Myriam Witvrouw

  DOI：10.1016/s0960-894x(01)00304-3

  日期：2001.7

  Design, synthesis and anti-HIV activity of a series of 2,3-diaryl-1,3-thiazolidin-4-ones are reported. Some derivatives proved to be highly effective in inhibiting HIV-1 replication at nanomolar concentrations thereby acting as non-nucleoside HIV-1 RT inhibitors (NNRTIs). SAR studies evidenced that the nature of the substituents at the 2 and 3 positions of the thiazolidinone nucleus largely influenced

  报道了一系列2，3-二芳基-1，3-噻唑烷酮-4-酮的设计，合成和抗HIV活性。一些衍生物被证明在纳摩尔浓度下抑制HIV-1复制非常有效，因此可以作为非核苷HIV-1 RT抑制剂（NNRTIs）。SAR研究表明，噻唑烷酮核的2和3位上的取代基的性质在很大程度上影响了这种新型有效抗病毒剂的体外抗HIV活性。
• Synthesis and anti-HIV activity of 2,3-diaryl-1,3-thiazolidin-4-(thi)one derivatives
  作者：Angela Rao、Anna Carbone、Alba Chimirri、Erik De Clercq、Anna Maria Monforte、Pietro Monforte、Christophe Pannecouque、Maria Zappalà

  DOI：10.1016/s0014-827x(02)01268-5

  日期：2002.9

  Several 2,3-diaryl-1,3-thiazolidine-4-thione derivatives and 2,3-diaryl-1,3-thiazolidin-4-ones bearing a methyl group at C-5 position have been synthesized and tested as anti-HIV agents, The results of the in vitro tests showed that some of them proved to be effective inhibitors of HIV-1 replication. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.