二乙基1-苯甲基-2-(甲基硫烷基)-1H-咪唑-4,5-二羧酸酯 | 1098-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 二乙基1-苯甲基-2-(甲基硫烷基)-1H-咪唑-4,5-二羧酸酯
• 英文名称: diethyl 1-benzyl-2-(methylthio)imidazole-4,5-dicarboxylate
• 英文别名: 1-benzyl-2-methylsulfanyl-1H-imidazole-4,5-dicarboxylic acid diethyl ester；2-Methylmercapto-1-benzyl-4,5-bis-ethoxycarbonyl-imidazol；Diethyl 1-benzyl-2-methylsulfanylimidazole-4,5-dicarboxylate
• CAS: 1098-38-0
• 化学式: C₁₇H₂₀N₂O₄S
• 分子量: 348.423
• InChiKey: MYGVEFURXDTEIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  95.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二乙基1-苯甲基-2-(甲基硫烷基)-1H-咪唑-4,5-二羧酸酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 [1-benzyl-5-(hydroxymethyl)-2-methylsulfanylimidazol-4-yl]methanol
  参考文献：
  名称：

  Design, synthesis, antineoplastic activity, and chemical properties of bis(carbamate) derivatives of 4,5-bis(hydroxymethyl)imidazole

  摘要：

  A series of bis(carbamate) derivatives of 1,2-substituted 4,5-bis(hydroxymethyl)imidazoles were prepared and evaluated against murine P388 lymphocytic leukemia. Electron-withdrawing substituents at either N-1 or C-2 gave rise to inactive compounds. However, electron-donating substituents gave active compounds and the 2-(methylthio)-1-methyl derivative 2i (carmethizole), as the bis(N-methylcarbamate), was found to be very active. The derivative 2i, referred to by the name carmethizole, was also shown to be active against the MX-1 mammary xenograft, the human amelanotic melanoma cell line (LOX) xenograft, the M5076 sarcoma, and L1210 lymphocytic leukemia. The solution stability, water solubility, pKa, and log P of carmethizole are also reported.

  DOI：

  10.1021/jm00121a023
• 作为产物：
  描述：

  diethyl 2-mercapto-4,5-imidazoledicarboxylate 在 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 二乙基1-苯甲基-2-(甲基硫烷基)-1H-咪唑-4,5-二羧酸酯
  参考文献：
  名称：

  Design, synthesis, antineoplastic activity, and chemical properties of bis(carbamate) derivatives of 4,5-bis(hydroxymethyl)imidazole

  摘要：

  A series of bis(carbamate) derivatives of 1,2-substituted 4,5-bis(hydroxymethyl)imidazoles were prepared and evaluated against murine P388 lymphocytic leukemia. Electron-withdrawing substituents at either N-1 or C-2 gave rise to inactive compounds. However, electron-donating substituents gave active compounds and the 2-(methylthio)-1-methyl derivative 2i (carmethizole), as the bis(N-methylcarbamate), was found to be very active. The derivative 2i, referred to by the name carmethizole, was also shown to be active against the MX-1 mammary xenograft, the human amelanotic melanoma cell line (LOX) xenograft, the M5076 sarcoma, and L1210 lymphocytic leukemia. The solution stability, water solubility, pKa, and log P of carmethizole are also reported.

  DOI：

  10.1021/jm00121a023

文献信息

• ANDERSON, W. K.;BHATTACHARJEE, D.;HOUSTON, D. M., J. MED. CHEM., 32,(1989) N, C. 119-127
  作者：ANDERSON, W. K.、BHATTACHARJEE, D.、HOUSTON, D. M.

  DOI：——

  日期：——