(2Z)-2-(2-chlorobenzylidene)-5,6-dihydroimidazo[2,1-b]thiazol-3(2H)-one | 1255207-84-1

• 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: (2Z)-2-(2-chlorobenzylidene)-5,6-dihydroimidazo[2,1-b]thiazol-3(2H)-one
• 英文别名: (2Z)-2-[(2-chlorophenyl)methylene]-5,6-dihydroimidazo[2,1-b]thiazol-3-one；(2Z)-2-[(2-chlorophenyl)methylidene]-5,6-dihydroimidazo[2,1-b][1,3]thiazol-3-one
• CAS: 1255207-84-1
• 化学式: C₁₂H₉ClN₂OS
• 分子量: 264.735
• InChiKey: QMUXVUWKUDKJLK-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2Z)-2-(2-chlorobenzylidene)-5,6-dihydroimidazo[2,1-b]thiazol-3(2H)-one 、 2,6-二氯苯甲腈 N-氧化物 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以61%的产率得到(9Z)-9-(2-chlorobenzylidene)-3-(2,6-dichlorophenyl)-5,6-dihydro[1,3]thiazolo[2′,3′:2,3]imidazo[1,2-d][1,2,4]oxadiazol-8(9H)-one
  参考文献：
  名称：

  通过1,3-偶极环氧化腈与咪唑[2,1–b] [1,3]噻唑-3（2H）-one的1,3-偶极环加成反应合成新型三杂环骨架

  摘要：

  （9 Z）-9-芳基亚甲基-3-（2,6-二氯苯基）-5,6-二氢[1,3]噻唑并[2'，3'：2,3]咪唑[1,2 - d ] [1,2,4]恶二唑8（9 ħ）通过用（2氧化腈的1,3-偶极环加成反应在中等产率制备-酮衍生物ž）-2-亚苄基-5， 6-二氢咪唑并[2,1- b ] [1,3]噻唑-3（2 H）-1。偶极亲电子的反应位点是咪唑并[2,1– b ] [1,3]噻唑的C═N，而不是芳基亚甲基的预期C═C。通过IR，MS，NMR光谱和元素分析对产物结构进行了彻底的表征。结果表明该反应以化学选择性和区域选择性进行。

  DOI：

  10.1002/jhet.632
• 作为产物：
  描述：

  2-((4,5-dihydro-1H-imidazol-2-yl)thio)acetic acid 在 吡啶 、 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 3.5h， 生成 (2Z)-2-(2-chlorobenzylidene)-5,6-dihydroimidazo[2,1-b]thiazol-3(2H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel thiazolidinone derivatives as potential anti-inflammatory agents

  摘要：

  The modulation of pro-inflammatory cytokines provides a target for controlling inflammatory diseases and attracts much attention in current anti-inflammatory drug development. Here, four series of thiazolidinone derivatives were synthesized and screened for anti-inflammatory activities. A majority of these compounds showed excellent inhibition on the expression of TNF-alpha and IL-6 in LPS-stimulated macrophages. Discussions are given regarding the structure activity relationships. Compounds 12d and 12h inhibited LPS-induced TNF-alpha and IL-6 release in a dose-dependent manner. Furthermore, 12d exhibited a significant protection against LPS-induced septic death in mouse model. Together, these data present a series of new thiazolidinones with potential therapeutic effects in acute inflammatory diseases and they could be important leads in the continuing anti-inflammatory drug research. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.010

文献信息

• Synthesis and biological evaluation of novel thiazolidinone derivatives as potential anti-inflammatory agents
  作者：Jie Hu、Yi Wang、Xiaoyan Wei、Xixi Wu、Gaozhi Chen、Gaozhong Cao、Xueqian Shen、Xiuhua Zhang、Qinqin Tang、Guang Liang、Xiaokun Li

  DOI：10.1016/j.ejmech.2013.04.010

  日期：2013.6

  The modulation of pro-inflammatory cytokines provides a target for controlling inflammatory diseases and attracts much attention in current anti-inflammatory drug development. Here, four series of thiazolidinone derivatives were synthesized and screened for anti-inflammatory activities. A majority of these compounds showed excellent inhibition on the expression of TNF-alpha and IL-6 in LPS-stimulated macrophages. Discussions are given regarding the structure activity relationships. Compounds 12d and 12h inhibited LPS-induced TNF-alpha and IL-6 release in a dose-dependent manner. Furthermore, 12d exhibited a significant protection against LPS-induced septic death in mouse model. Together, these data present a series of new thiazolidinones with potential therapeutic effects in acute inflammatory diseases and they could be important leads in the continuing anti-inflammatory drug research. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis of a Novel Triheterocyclic Framework via 1,3-Dipolar Cycloaddition of a Nitrile Oxide with Imidazo[2,1-<i>b</i>][1,3]thiazole-3(2<i>H</i>)-ones
  作者：Xiaofang Li、Aiting Zheng、Bin Liu、Xianyong Yu、Pinggui Yi

  DOI：10.1002/jhet.632

  日期：2013.7

  A novel series of (9Z)‐9‐arylmethylidene‐3‐(2,6‐dichlorophenyl)‐5,6‐dihydro[1,3]thiazolo[2′,3′:2,3]imidazo [1,2‐d][1,2,4]oxadiazol‐8(9H)‐one derivatives were prepared in moderate yields by the 1,3‐dipolar cycloaddition reaction of a nitrile oxide with (2Z)‐2‐arylmethylidene‐5,6‐dihydroimidazo [2,1‐b][1,3]thiazol‐3(2H)‐ones. The reaction site of the dipolarphile is the C═N of imidazo[2,1‐b][1,3]thiazole

  （9 Z）-9-芳基亚甲基-3-（2,6-二氯苯基）-5,6-二氢[1,3]噻唑并[2'，3'：2,3]咪唑[1,2 - d ] [1,2,4]恶二唑8（9 ħ）通过用（2氧化腈的1,3-偶极环加成反应在中等产率制备-酮衍生物ž）-2-亚苄基-5， 6-二氢咪唑并[2,1- b ] [1,3]噻唑-3（2 H）-1。偶极亲电子的反应位点是咪唑并[2,1– b ] [1,3]噻唑的C═N，而不是芳基亚甲基的预期C═C。通过IR，MS，NMR光谱和元素分析对产物结构进行了彻底的表征。结果表明该反应以化学选择性和区域选择性进行。