(5-(3-bromo-4-hydroxybenzylidene)thiazolidine-2,4-dione)

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (5-(3-bromo-4-hydroxybenzylidene)thiazolidine-2,4-dione)
• 英文别名: (5Z)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
• 化学式: C₁₀H₆BrNO₃S
• 分子量: 300.133
• InChiKey: BQYDIAPNPDEQHK-YWEYNIOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5-(3-bromo-4-hydroxybenzylidene)thiazolidine-2,4-dione) 、 3-苯基丙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以88.9%的产率得到(Z)-2-bromo-4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl 3-phenylpropanoate
  参考文献：
  名称：

  THIAZOLIDINEDIONE DERIVATIVE AND USE THEREOF

  摘要：

  提供了由公式1a和1b中的任一表示的新化合物及其用途。提供了由公式1a和1b中的任一表示的新噻唑烷二酮衍生物以及含有它们的药物组合物。

  公开号：

  US20190016695A1
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 3-溴-4-羟基苯甲醛 在 哌啶 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 以94.1%的产率得到(5-(3-bromo-4-hydroxybenzylidene)thiazolidine-2,4-dione)
  参考文献：
  名称：

  THIAZOLIDINEDIONE DERIVATIVE AND USE THEREOF

  摘要：

  提供了由公式1a和1b中的任一表示的新化合物及其用途。提供了由公式1a和1b中的任一表示的新噻唑烷二酮衍生物以及含有它们的药物组合物。

  公开号：

  US20190016695A1

文献信息

• Thiazolidinedione derivative and use thereof
  申请人：INDUSTRY-ACADEMIC COOPERATION FOUNDATION CHOSUN UNIVERSITY

  公开号：US10787425B2

  公开（公告）日：2020-09-29

  Provided are a novel compound represented by any one of Formulae 1a and 1b and use thereof. Provided are novel thiazolidinedione derivatives represented by any one of Formulae 1a and 1b and pharmaceutical compositions containing the same.

  提供由式 1a 和 1b 中任一项代表的新型化合物及其用途。提供了由式 1a 和 1b 中任一项代表的新型噻唑烷二酮衍生物及其药物组合物。
• NOVEL LIGANDS FOR THE HisB10 Zn2+ SITES OF THE R-STATE INSULIN HEXAMER
  申请人：NOVO NORDISK A/S

  公开号：EP1429763B1

  公开（公告）日：2007-05-30
• [EN] USE OF MODULATORS OF NEET PROTEINS FOR THE TREATMENT OF INFECTION<br/>[FR] UTILISATION DE MODULATEURS DE PROTÉINES NEET POUR LE TRAITEMENT D'UNE INFECTION
  申请人：ENYO PHARMA

  公开号：WO2019154958A1

  公开（公告）日：2019-08-15

  The present invention relates to the use of modulators of NEET proteins for the treatment of infection, in particular viral or bacterial infection.
• THIAZOLIDINEDIONE DERIVATIVE AND USE THEREOF
  申请人：INDUSTRY-ACADEMIC COOPERATION FOUNDATION CHOSUN UNIVERSITY

  公开号：US20190016695A1

  公开（公告）日：2019-01-17

  Provided are a novel compound represented by any one of Formulae 1a and 1b and use thereof. Provided are novel thiazolidinedione derivatives represented by any one of Formulae 1a and 1b and pharmaceutical compositions containing the same.

  提供了由公式1a和1b中的任一表示的新化合物及其用途。提供了由公式1a和1b中的任一表示的新噻唑烷二酮衍生物以及含有它们的药物组合物。
• Pharmacological Exploitation of the Peroxisome Proliferator-Activated Receptor γ Agonist Ciglitazone To Develop a Novel Class of Androgen Receptor-Ablative Agents
  作者：Jian Yang、Shuo Wei、Da-Sheng Wang、Yu-Chieh Wang、Samuel K. Kulp、Ching-Shih Chen

  DOI：10.1021/jm701212m

  日期：2008.4.1

  On the basis of our finding that the peroxisome proliferator-activated receptor gamma (PPAR gamma) agonist ciglitazone at high doses was able to mediate PPAR gamma-independent transcriptional repression of androgen receptor (AR) in a tumor cell-specific manner, we used Delta 2CG, a PPAR gamma-inactive analogue of ciglitazone, to conduct lead optimization to develop a novel class of AR-ablative agents. Structure-activity analysis indicates a high degree of flexibility in realigning Delta 2CG's structural moieties without compromising potency in AR repression, as evidenced by the higher AR-ablative activity of the permuted isomer 9 [(Z)-5-(4-hydroxybenzylidene)3-(1-methylcyclohexylmethyl)thiazolidine-2,4-dione]. Further modificiations of 9 gave rise to 12 [(Z)-5-(4-hydroxy-3-trifluoromethylbenzylidene)-3-(1-methylcyclohexylmethyl)thiazolidine-2,4-dione], which completely inhibited AR expression in LNCaP cells at low micromolar concentrations. This AR down-regulation led to growth inhibition in LNCaP cells through apoptosis induction. Moreover, the role of AR repression in the antiproliferative effect of compound 12 was validated by the differential inhibition of cell viability between androgen-responsive and androgen-nonresponsive cells.