methyl 1-methyl-2-oxo-5-cyano-2,3-dihydroimidazole-4-carboxylate | 117121-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 1-methyl-2-oxo-5-cyano-2,3-dihydroimidazole-4-carboxylate
• 英文别名: methyl 4-cyano-3-methyl-2-oxo-1H-imidazole-5-carboxylate
• CAS: 117121-09-2
• 化学式: C₇H₇N₃O₃
• 分子量: 181.151
• InChiKey: VSLZAZQHHZINJZ-UHFFFAOYSA-N

物化性质

• 熔点：
  257-259 °C(Solv: methanol (67-56-1))
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-methyl-2-oxo-5-cyano-2,3-dihydroimidazole-4-carboxylate 在 盐酸 作用下， 反应 1.0h， 以90%的产率得到1-methyl-2-oxo-2,3-dihydroimidazole-4-carboxylic acid
  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：

  2-amino-3-<(methoxymethylene)amino>maleonitrile 在 盐酸 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙腈 为溶剂， 反应 109.0h， 生成 methyl 1-methyl-2-oxo-5-cyano-2,3-dihydroimidazole-4-carboxylate
  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：——