5-(吡啶-3-基亚甲基)-2-硫代-1,3-噻唑烷-4-酮 | 3785-78-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-(吡啶-3-基亚甲基)-2-硫代-1,3-噻唑烷-4-酮
• 英文名称: (5Z)-5-(pyridin-3-ylmethylidene)-2-thioxo-1,3-thiazolidin-4-one
• 英文别名: (5Z)-5-(pyridin-3-ylmethylene)-2-thioxo-1,3-thiazolidin-4-one；(Z)-5-(pyridin-3-ylmethylene)-2-thioxothiazolidin-4-one；5-(3-Pyridylmethylene)rhodanine；(5Z)-5-(pyridin-3-ylmethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 3785-78-2
• 化学式: C₉H₆N₂OS₂
• 分子量: 222.291
• InChiKey: WCMBSDRTRVIVGG-DAXSKMNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 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：
  99.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  3-吡啶甲醛 、 罗丹宁 反应 0.05h， 以52%的产率得到5-(吡啶-3-基亚甲基)-2-硫代-1,3-噻唑烷-4-酮
  参考文献：
  名称：

  Synthesis and antifungal activity of (Z)-5-arylidenerhodanines

  摘要：

  An efficient microwave-assisted synthesis of new (Z)-5-arylidenerhodanines under solvent-free conditions is described and their in vitro antifungal activity was evaluated following the CLSI (formerly NCCLS) guidelines against a panel of both standardized and clinical opportunistic pathogenic fungi. An analysis of the structure-activity relationship (SAR) along with computational studies showed that the most active compounds (F- and CF3-substituted rbodanines) possess high log P values and low polarizability. Mechanism-based assays suggest that active compounds neither would bind to ergosterol nor would produce a damage to the fungal membrane. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.038

文献信息

• Thiazolidinone derivatives as hypoglycemic agents and for treating Alzheimer's disease
  申请人：ELI LILLY AND COMPANY

  公开号：EP0587377A2

  公开（公告）日：1994-03-16

  Provided are methods for treating hyperglycemia and Alzheimer's disease utilizing certain rhodanine derivatives. Certain of the rhodanine derivatives utilized in the instant methods are novel and, accordingly, such compounds, process for preparing same and pharmaceutical formulations thereof, are also provided.

  本发明提供了利用某些罗丹宁衍生物治疗高血糖和阿尔茨海默病的方法。在本方法中使用的某些罗丹宁衍生物是新颖的，因此还提供了此类化合物、其制备工艺和药物制剂。
• Compounds useful as hypoglycemic agents and for treating Alzheimer's disease
  申请人：ELI LILLY AND COMPANY

  公开号：EP0915090A1

  公开（公告）日：1999-05-12

  Provided are methods for treating hyperglycemia and Alzheimer's disease utilizing certain rhodanine derivatives. Certain of the rhodanine derivatives utilized in the instant methods are novel and, accordingly, such compounds, process for preparing same and pharmaceutical formulations thereof, are also provided.

  本发明提供了利用某些罗丹宁衍生物治疗高血糖和阿尔茨海默病的方法。在本方法中使用的某些罗丹宁衍生物是新颖的，因此还提供了此类化合物、其制备工艺和药物制剂。
• Rational design of apoptosis signal-regulating kinase 1 inhibitors: Discovering novel structural scaffold
  作者：Galyna P. Volynets、Volodymyr G. Bdzhola、Andriy G. Golub、Anatoliy R. Synyugin、Maksym A. Chekanov、Oleksandr P. Kukharenko、Sergiy M. Yarmoluk

  DOI：10.1016/j.ejmech.2012.09.022

  日期：2013.3

  Increased activity of apoptosis signal-regulating kinase 1 (ASK1) is associated with a number of human disorders and the inhibitors of ASK1 may become important compounds for pharmaceutical application. Here we report novel ASK1 inhibitor scaffold, namely 5-(5-Phenyl-furan-2-ylmethylene)-2-thioxo-thiazolidin-4-one, that has been identified using virtual screening and biochemical tests. A series of derivatives has been synthesized and evaluated in vitro towards human protein kinase ASK1. It was revealed that the most active compounds 4-((5Z)-5-[5-(4-bromophenyl)-2-furyl]methylene}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)butanoic acid and 6-((5Z)-5-[5-(4-bromophenyl)-2-furyl]methylene}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)hexanoic acid inhibit ASK1 with IC50 of 0.2 mu M. Structure activity relationships of 33 derivatives of 5-(5-Phenyl-furan-2-ylmethylene)-2-thioxo-thiazolidin-4-one have been studied and binding mode of this chemical class has been predicted. (C) 2012 Elsevier Masson SAS. All rights reserved.
• US5523314A
  申请人：——

  公开号：US5523314A

  公开（公告）日：1996-06-04
• US5661168A
  申请人：——

  公开号：US5661168A

  公开（公告）日：1997-08-26