methyl 4-(6-amino-5-(2-carbamoylhydrazineylidene)hexan-3-yl)benzoate hydrochloride | 102152-96-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: methyl 4-(6-amino-5-(2-carbamoylhydrazineylidene)hexan-3-yl)benzoate hydrochloride
• CAS: 102152-96-5
• 化学式: C₁₅H₂₂N₄O₃*ClH
• 分子量: 342.826
• InChiKey: BQGQYNFVAOOHRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  119.8
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 4-(6-amino-5-(2-carbamoylhydrazineylidene)hexan-3-yl)benzoate hydrochloride 在 2,4,6-三甲基吡啶 、 sodium ethanolate 作用下， 反应 19.0h， 生成 1-<(2,4-diamino-5-nitropyrimidin-6-yl)amino>-4-(p-carbomethoxyphenyl)-2-hexanone trifluoreacetate
  参考文献：
  名称：

  Synthesis and biological activity of resolved carbon-10 diastereomers of 10-methyl- and 10-ethyl-10-deazaminopterin

  摘要：

  Synthesis and evaluation of the antitumor drugs 10-methyl- and 10-ethyl-10-deazaminopterin (15a,b) were previously reported for the diastereomeric mixtures, lacking resolution at the C-10 position. In order to assess biological properties of the individual diastereomers, the C-10 isomers of 4-amino-4-deoxy-10-methyl- and 10-ethyl-10-deazapteroic acids (13a,b) were prepared by total synthesis. Coupling with L-glutamate afforded the appropriate diastereomers of the title compounds. Biochemical, transport, and cell growth inhibitory properties in L1210 cells and folate-dependent bacteria were measured. Differences were generally less than 2-fold between diastereomeric pairs, but a factor of 3 was noted for d,L-15b vs. l,L-15b in inhibition of DHFR from L1210 cells and in cytotoxicity toward L1210 cells. An in vivo comparison of the isomers of 15b with racemic compound against L1210 in mice did not show a significant efficacy difference (ILS) among the compounds. However, d,L-15b showed an acute toxicity about 2.5 times that of l,L-15b.

  DOI：

  10.1021/jm00156a026