2-((4,5-dihydro-1H-imidazol-2-yl)thio)acetic acid | 19951-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-((4,5-dihydro-1H-imidazol-2-yl)thio)acetic acid
• 英文别名: [(4,5-Dihydroimidazol-3-ium-2-yl)thio]acetate；2-(4,5-dihydro-1H-imidazol-3-ium-2-ylsulfanyl)acetate
• CAS: 19951-23-6
• 化学式: C₅H₈N₂O₂S
• mdl: MFCD00457419
• 分子量: 160.197
• InChiKey: MXQQZVRKFFMIKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((4,5-dihydro-1H-imidazol-2-yl)thio)acetic acid 在 哌啶 、 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 1-Thia-2-benzyliden-4,7-diaza-bicyclo<8-4>-octen-(7)-on-(3)
  参考文献：
  名称：

  Reactions of Ethylenethiourea with α- and β-Halo Acids and Derivatives¹

  摘要：

  DOI：

  10.1021/jo01030a013
• 作为产物：
  描述：

  亚乙基硫脲 、 氯乙酸 以 丙酮 为溶剂， 反应 8.0h， 以28%的产率得到2-((4,5-dihydro-1H-imidazol-2-yl)thio)acetic acid
  参考文献：
  名称：

  Thioimidazoline based compounds reverse glucocorticoid resistance in human acute lymphoblastic leukemia xenografts

  摘要：

  糖皮质激素是小儿急性淋巴细胞白血病化疗方案的重要组成部分，对糖皮质激素治疗的初次反应不佳预示着较差的预后。

  DOI：

  10.1039/c5ob00779h

文献信息

• Effect of salicylates and zinc salts on leukemic cells
  作者：A. P. Orlov、M. A. Orlov、T. P. Trofimov、E. Yu. Osipova、A. N. Proshin

  DOI：10.1007/s11172-016-1525-6

  日期：2016.7

  The prospects of the action of different types of chelating agents capable of binding to zinc, and salicylate ion comprising compounds on leukemic cells are reviewed. Survival rates and therapeutic indexes were compared.

  综述了能够与锌结合的不同类型螯合剂和含有水杨酸离子的化合物对白血病细胞的作用前景。比较生存率和治疗指标。
• New data on the alkylation of cyclic thioureas with α-halo-carboxylic acids and their esters. 1. Alkylation of ethylene thiourea
  作者：P. M. Kushakova、S. M. Ramsh、A. V. Garabadgiu

  DOI：10.1007/s10593-006-0075-5

  日期：2006.2
• 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.
• The Rearrangement of 2-Carboxymethylmercaptoimidazolidine
  作者：JAMES A. VanALLAN

  DOI：10.1021/jo01108a011

  日期：1956.2
• 2-Carboxymethylmercaptobenzimidazole and Related Compounds^*
  作者：J. A. VanALLAN

  DOI：10.1021/jo01107a004

  日期：1956.1