2-Amino-4-ethoxycarbonylmethyl-3-(2-oxo-2-m-tolyl-ethyl)-thiazol-3-ium; bromide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Amino-4-ethoxycarbonylmethyl-3-(2-oxo-2-m-tolyl-ethyl)-thiazol-3-ium; bromide
• 英文别名: Ethyl 2-[2-amino-3-[2-(3-methylphenyl)-2-oxoethyl]-1,3-thiazol-3-ium-4-yl]acetate;bromide
• 化学式: Br*C₁₆H₁₉N₂O₃S
• 分子量: 399.308
• InChiKey: DDOOMQXYWUYFDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.08
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Amino-4-ethoxycarbonylmethyl-3-(2-oxo-2-m-tolyl-ethyl)-thiazol-3-ium; bromide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 [3-(2-Hydroxy-2-m-tolyl-ethyl)-2-imino-thiazolidin-(4E)-ylidene]-acetic acid ethyl ester
  参考文献：
  名称：

  Imidazo[2,1-b]thiazole derivatives. XI. Modulation of the CD2-receptor of human T trypsinized lymphocytes by several imidazo[2,1-b]thiazoles

  摘要：

  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.

  DOI：

  10.1016/0223-5234(94)90101-5

文献信息

• 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.