Chlorhydrate de (phenyl-6 imidazo<2,1-b>thiazolyl-3) acetate d'ethyle | 57626-45-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Chlorhydrate de (phenyl-6 imidazo<2,1-b>thiazolyl-3) acetate d'ethyle
• 英文别名: (6-phenyl-imidazo[2,1-b]thiazol-3-yl)-acetic acid ethyl ester; hydrobromide；ethyl 2-(6-phenylimidazo[2,1-b][1,3]thiazol-3-yl)acetate;hydrobromide
• CAS: 57626-45-6
• 化学式: BrH*C₁₅H₁₄N₂O₂S
• 分子量: 367.266
• InChiKey: WJCUUSCQXDJSHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.41
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.19
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Chlorhydrate de (phenyl-6 imidazo<2,1-b>thiazolyl-3) acetate d'ethyle 在 sodium carbonate 作用下， 以 氯仿 为溶剂， 反应 0.33h， 以73%的产率得到(Phenyl-6 imidazo<2,1-b>thiazolyl-3) acetate d'ethyle
  参考文献：
  名称：

  Meakins, G. Denis; Musk, Sally R. R.; Robertson, Colin A., Journal of the Chemical Society. Perkin transactions I, 1989, # 3, p. 643 - 648

  摘要：

  DOI：
• 作为产物：
  描述：

  Bromhydrate d'(imino-2 phenacyl-3 thiazolinyl-4)acetate d'ethyle 在 乙醇 作用下， 生成 Chlorhydrate de (phenyl-6 imidazo<2,1-b>thiazolyl-3) acetate d'ethyle
  参考文献：
  名称：

  Dérivés de l'imidazo[2,1-b]thiazole X. Propriétés fongistatiques de 2-aminothiazoles et de 6-aryl imidazo[2,1-b]thiazoles substitués respectivement en 4 et en 3 par un reste aryléthyle, aroylméthyle, β-hydroxy β-aryléthyle et éthoxycarbonylméthyle

  摘要：

  Several 2-aminothiazoles, substituted in 4 with an ethylacetate, aroylmethyl, beta-hydroxy beta-arylethyl or arylethyl chain, were combined with omega-bromoacetophenones in order to obtain the corresponding 3-substituted 6-arylimidazo[2,1-b]thiazoles to perform fungistatic tests. The ethyl (2-aminothiazole-4-yl) acetates led to the expected imidazothiazoles. This was not noted in the other cases. Thus, the presence of an aroylmethyl residue considerably decrease the reactivity of the aminothiazole. The transformation of the ketonic carbonyl to alcohol II, or even better, to methylene is necessary for the condensation to be effected with omega-bromoacetophenones. The yield of this reaction is low. The results of fungistatic tests show the interest of the aminothiazole derivatives with an aroylmethyl on Candida albicans, Aspergillus fumigatus, Epidermophyton floccosum. The best activity is observed when the phenyl has one or several methyl or methoxy groups. The imidazothiazole compounds, although there is a substitution in 6, show lower efficiency.

  DOI：

  10.1016/0223-5234(90)90192-6

文献信息

• Novel imidazo[2,1‐ <i>b</i> ]thiazole‐based anticancer agents as potential focal adhesion kinase inhibitors: Synthesis, in silico and in vitro evaluation
  作者：Faika Başoğlu、Nuray Ulusoy‐Güzeldemirci、Gülşen Akalın‐Çiftçi、Serap Çetinkaya、Abdulilah Ece

  DOI：10.1111/cbdd.13896

  日期：2021.8

  The purpose of this study was to synthesize imidazo[2,1-b]thiazole derivatives, characterize them with spectroscopical techniques and investigate for cytotoxic and apoptotic effects on glioma C6 cancer cell line. The in vitro anticancer activities were also investigated against focal adhesion kinase. Most of the compounds, particularly the derivatives carrying 3-oxo-1-tiya-4-azaspiro[4.5]decane moiety

  本研究的目的是合成咪唑[2,1- b]噻唑衍生物，用光谱技术对它们进行表征，并研究对神经胶质瘤 C6 癌细胞系的细胞毒性和凋亡作用。还研究了针对粘着斑激酶的体外抗癌活性。大多数化合物，特别是带有 3-oxo-1-tiya-4-azaspiro[4.5]decane 部分的衍生物，与参考药物顺铂相比，表现出更高或相当的活性。在螺噻唑烷酮环的第八位和第二位具有甲基、丙基、苯基部分的化合物显示出高的 FAK 抑制活性。此外，分子对接研究揭示了合成化合物的结合模式。揭示了与位于活性位点的氨基酸残基的关键相互作用。
• Imidazo[2,1-b]thiazole derivatives. XI. Modulation of the CD2-receptor of human T trypsinized lymphocytes by several imidazo[2,1-b]thiazoles
  作者：S Harraga、L Nicod、JP Drouhin、A Xicluna、JJ Panouse、E Seilles、JF Robert

  DOI：10.1016/0223-5234(94)90101-5

  日期：1994.1

  About 40 substituted imidazo[2,1-b]thiazoles were obtained in order to study their in vitro immunological effect on the modulation of the expression of human T trypsinized lymphocytes by the CD2 receptor. A synthetic program was developed to introduce either an oxygenated function, such as ester (11, 14), acid (12) and arylketonic groups (9, 13, 15), or two groups, such as an aryl and an ester (1, 6, 8), an acid (3, 7) or a hydrazide (2). These compounds were examined by an E-rosette-forming-cell test, and display a positive drug efficacity index, suggesting a regeneration effect on the expression of CD2 receptors. The following structural parameters are favourable: an aryl moiety on the C-6 with a methoxy or nitro group; and an ethyl ester on the C-3, a double bond to the 2,3-position (the 5,6-position is ineffective). Acid and hydrazide functions or the loss of phenyl group on the C-6 decrease this activity. If the aryl group is on the C-3 or C-2 side chain, the activity is weaker and more so for the latter. However, the most interesting derivatives are less immunostimulating than levamisole hydrochloride.
• ROBERT J.-F.; XICLUNA A.; PANOUSE J. J., EUR. J. MED. CHEM., 1975, 10, NO 1, 59-64
  作者：ROBERT J.-F.、 XICLUNA A.、 PANOUSE J. J.

  DOI：——

  日期：——
• Robert, Jean-Francois; Panouse, Jacques J., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 343 - 348
  作者：Robert, Jean-Francois、Panouse, Jacques J.

  DOI：——

  日期：——