3-(2-hydroxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one | 2256-47-5

• 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: 3-(2-hydroxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one
• 英文别名: 3-(2-hydroxyethyl)-2-(phenylimino)thiazolidin-4-one；(Z)-3-(2-Hydroxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one；3-(2-hydroxyethyl)-2-phenylimino-1,3-thiazolidin-4-one
• CAS: 2256-47-5
• 化学式: C₁₁H₁₂N₂O₂S
• 分子量: 236.294
• InChiKey: JDIRJYHULVCRRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(4-Oxo-2-phenylimino-1,3-thiazolidin-3-yl)acetaldehyde
  参考文献：
  名称：

  Tethered thiazolidinone dimers as inhibitors of the bacterial type III secretion system

  摘要：

  Disruption of protein-protein interactions by small molecules is achievable but presents significant hurdles for effective compound design. In earlier work we identified a series of thiazolidinone inhibitors of the bacterial type III secretion system (T3SS) and demonstrated that this scaffold had the potential to be expanded into molecules with broad-spectrum anti-Gram negative activity. We now report on one series of thiazolidinone analogs in which the heterocycle is presented as a dimer at the termini of a series of linkers. Many of these dimers inhibited the T3SS-dependent secretion of a virulence protein at concentrations lower than that of the original monomeric compound identified in our screen. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.047
• 作为产物：
  描述：

  在 四丁基氟化铵 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以1.92 g的产率得到3-(2-hydroxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Tethered thiazolidinone dimers as inhibitors of the bacterial type III secretion system

  摘要：

  Disruption of protein-protein interactions by small molecules is achievable but presents significant hurdles for effective compound design. In earlier work we identified a series of thiazolidinone inhibitors of the bacterial type III secretion system (T3SS) and demonstrated that this scaffold had the potential to be expanded into molecules with broad-spectrum anti-Gram negative activity. We now report on one series of thiazolidinone analogs in which the heterocycle is presented as a dimer at the termini of a series of linkers. Many of these dimers inhibited the T3SS-dependent secretion of a virulence protein at concentrations lower than that of the original monomeric compound identified in our screen. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.047

文献信息

• Synthesis of metronidazole based thiazolidinone analogs as promising antiamoebic agents
  作者：Mohammad Fawad Ansari、Afreen Inam、Kamal Ahmad、Shehnaz Fatima、Subhash M. Agarwal、Amir Azam

  DOI：10.1016/j.bmcl.2020.127549

  日期：2020.12

  many side effects. The present study describes the synthesis of a series of metronidazole based thiazolidinone analogs via Knoevenagel condensation of 4-[2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethoxy]benzaldehyde 1 with various thiazolidinone derivatives 2-14 to get the new scaffold (15-27) having better activity and lesser toxicity. Six compounds have shown better efficacy and lesser cytotoxicity than

  甲硝唑及其衍生物被广泛用于阿米巴病的治疗。但是，甲硝唑被认为是标准药物，但有许多副作用。本研究描述的基于噻唑烷酮类似物的一系列甲硝唑的合成通过4- Knoevenagel缩合[2-（2-甲基-5-硝基-1- ħ咪唑-1-基）乙氧基]苯甲醛1与各种噻唑烷酮衍生物2 -14得到新的支架（15-27），具有更好的活性和更低的毒性。与标准甲硝唑相比，六种化合物对HM1具有更好的疗效，并具有较小的细胞毒性，这是对溶组织变形杆菌的IMSS菌株。这些化合物可能会解决耐药性问题，并可能有效地确定将来针对Eh OASS的药物发现的潜在替代品。
• Synthesis and in vitro evaluation of 5-arylidene-3-hydroxyalkyl-2-phenylimino-4-thiazolidinones with antidegenerative activity on human chondrocyte cultures
  作者：Rosaria Ottanà、Rosanna Maccari、Rosella Ciurleo、Maria Gabriella Vigorita、Anna Maria Panico、Venera Cardile、Floriana Garufi、Simone Ronsisvalle

  DOI：10.1016/j.bmc.2007.09.001

  日期：2007.12

  5-Arylidene-3-hydroxyalkyl-2-phenylimino-4-thiazolidinones (7,8) were synthesized and evaluated for their antidegenerative activity on human chondrocyte cultures stimulated by IL-1 beta. This in vitro model has proven to be a useful experimental model to reproduce the mechanisms involved in arthritic diseases. The cell viability, the amount of GAGs, the production of NO and PGE(2) and the inhibition of MMP-3 were measured. Several thiazolidinones 7 and 8 exhibited the ability to block the production or action of the degenerative factors induced by IL-1 beta. (c) 2007 Elsevier Ltd. All rights reserved.