6-(2-Hydroxyphenyl)imidazo[2,1-b]thiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(2-Hydroxyphenyl)imidazo[2,1-b]thiazole
• 英文别名: 2-(imidazo[2,1-b]thiazol-6-yl)phenol；2-Imidazo[2,1-b][1,3]thiazol-6-ylphenol
• 化学式: C₁₁H₈N₂OS
• 分子量: 216.263
• InChiKey: GABZUTFLODBPMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2'-二硫二吡啶 、 6-(2-Hydroxyphenyl)imidazo[2,1-b]thiazole 在 双氧水 、 碘 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以85%的产率得到2-[5-(pyridin-2-ylthio)imidazo[2,1-b]thiazol-6-yl]phenol
  参考文献：
  名称：

  Direct Sulfenylation of Imidazoheterocycles with Disulfides in an Iodine–Hydrogen Peroxide System

  摘要：

  Imidazoheterocycles undergo efficient and regioselective sulfenylation with disulfides using the iodine/hydrogen peroxide system in ethanol at 25 degrees C. This green strategy tolerates a wide range of functional groups to afford diverse sulfenylated imidazoheterocycles in high yields. Moreover, the fipronil (a pesticide) skeleton can be readily attached to imidazoheterocycles using this strategy, which is significant in drug development.

  DOI：

  10.1055/s-0034-1379941
• 作为产物：
  描述：

  6-(2-Methoxy-phenyl)-imidazo[2,1-b]thiazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到6-(2-Hydroxyphenyl)imidazo[2,1-b]thiazole
  参考文献：
  名称：

  6-(Hydroxyphenyl)imidazo[2,1-b]thiazoles as Potential Antiinflammatory Agents: Effects on Human Neutrophil Functions

  摘要：

  报道了从相应的甲氧基衍生物合成与左旋咪唑相关的6-(羟基苯基)咪唑并[2,1-b]噻唑。这些化合物在体外中性粒细胞活化方面进行了测试，即由趋化剂诱导的运动、由激动剂引发的超氧化物生成和溶菌酶脱颗粒。这些功能在细胞脉冲后经不同浓度药物评估。一些衍生物显示出显著的抑制作用，在某些情况下比母化合物更强效。

  DOI：

  10.1135/cccc20000267

文献信息

• [EN] COMPOUNDS FOR TREATING DUCHENNE MUSCULAR DYSTROPHY<br/>[FR] COMPOSÉS POUR TRAITER LA DYSTROPHIE MUSCULAIRE DE DUCHENNE
  申请人：SUMMIT CORP PLC

  公开号：WO2009013477A1

  公开（公告）日：2009-01-29

  Compounds of general formula (I), wherein X1, X2, X3, R1, R2, R3, Y and Z are as defined herein are useful for the treatment and prevention of Duchenne muscular dystrophy, Becker muscular dystrophy and cachexia.

  通式（I）的化合物，其中X1、X2、X3、R1、R2、R3、Y和Z的定义如本文所述，对于治疗和预防杜兴氏肌肉萎缩症、贝克氏肌肉萎缩症和消瘦症是有用的。
• Synthesis of Imidazoheterocycle-Hydrazine, -Carbamate, and Imidazocinnoline Derivatives
  作者：Mao-Lin Hu、Ri-Yuan Tang、Jing Jiao、Li Xu、Wenxu Zheng、Ping Xiong

  DOI：10.1055/s-0036-1588374

  日期：——

  Abstract Iron-catalyzed amination of imidazoheterocycles with diethyl azodicarboxylate (DEAD) under mild conditions has been developed. This strategy tolerates a wide range of functional groups to afford diverse imidazoheterocycle-hydrazines in moderate to excellent yields. Significantly, imidazoheterocycle hydrazines can be converted into imidazoheterocycle carbamates and imidazocinnolines. Iron-catalyzed

  摘要 已经开发了在温和条件下用偶氮二羧酸二乙酯（DEAD）进行铁催化的咪唑杂环杂环胺化反应。该策略可耐受各种官能团，以中等至极好的收率提供各种咪唑杂环-肼。重要的是，咪唑杂环杂环肼可以转化为氨基咪唑杂环氨基甲酸酯和咪唑啉啉。 已经开发了在温和条件下用偶氮二羧酸二乙酯（DEAD）进行铁催化的咪唑杂环杂环胺化反应。该策略可耐受各种官能团，以中等至极好的收率提供各种咪唑杂环-肼。重要的是，咪唑杂环杂环肼可以转化为氨基咪唑杂环氨基甲酸酯和咪唑啉啉。
• COMPOUNDS FOR TREATING DUCHENNE MUSCULAR DYSTROPHY
  申请人：Summit Corporation Plc

  公开号：EP2167508A1

  公开（公告）日：2010-03-31
• Direct Sulfenylation of Imidazoheterocycles with Disulfides in an Iodine–Hydrogen Peroxide System
  作者：Fan Chen、Ri-Yuan Tang、Xiao-Ming Ji、Shu-Juan Zhou、Xing-Guo Zhang

  DOI：10.1055/s-0034-1379941

  日期：——

  Imidazoheterocycles undergo efficient and regioselective sulfenylation with disulfides using the iodine/hydrogen peroxide system in ethanol at 25 degrees C. This green strategy tolerates a wide range of functional groups to afford diverse sulfenylated imidazoheterocycles in high yields. Moreover, the fipronil (a pesticide) skeleton can be readily attached to imidazoheterocycles using this strategy, which is significant in drug development.
• 6-(Hydroxyphenyl)imidazo[2,1-b]thiazoles as Potential Antiinflammatory Agents: Effects on Human Neutrophil Functions
  作者：Aldo Andreani、Mirella Rambaldi、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Serena Traniello、Alessio Cariani、Olivia Rizzuti、Susanna Spisani

  DOI：10.1135/cccc20000267

  日期：——

  Synthesis of 6-(hydroxyphenyl)imidazo[2,1-b]thiazoles related to levamisole from the corresponding methoxy derivatives is reported. These compounds were tested on in vitro neutrophil activation, namely locomotion induced by chemoattractants, superoxide generation and lysozyme degranulation triggered by agonists. These functions were evaluated after cell pulse with different concentrations of the drugs. Several derivatives showed significant inhibitory effects, in some cases more potent than the parent compound.

  报道了从相应的甲氧基衍生物合成与左旋咪唑相关的6-(羟基苯基)咪唑并[2,1-b]噻唑。这些化合物在体外中性粒细胞活化方面进行了测试，即由趋化剂诱导的运动、由激动剂引发的超氧化物生成和溶菌酶脱颗粒。这些功能在细胞脉冲后经不同浓度药物评估。一些衍生物显示出显著的抑制作用，在某些情况下比母化合物更强效。