diethyl N-(p-aminobenzyl)-L-glutamate | 83314-87-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl N-(p-aminobenzyl)-L-glutamate
• 英文别名: N-(4-aminobenzyl)-L-glutamic diethylester；diethyl (2S)-2-[(4-aminophenyl)methylamino]pentanedioate
• CAS: 83314-87-8
• 化学式: C₁₆H₂₄N₂O₄
• 分子量: 308.378
• InChiKey: QNOWIDQFZCZYLS-AWEZNQCLSA-N

物化性质

• 沸点：
  448.6±45.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl N-(p-aminobenzyl)-L-glutamate 在 barium dihydroxide 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 50.0h， 生成 N-<<<(2,4-diaminopteridin-6-yl)methyl>amino>benzyl>-L-glutamic acid
  参考文献：
  名称：

  Methotrexate analogs. 16. Importance of the side-chain amide carbonyl group as a structural determinant of biological activity

  摘要：

  N-[[[(2,4-Diaminopteridin-6-yl)methyl]amino]benzyl]-L-glutamic acid ("deoxoaminopterin", 1), a new aminopterin analogue containing a CH2 group in the side chain in place of the amide C = O, was synthesized by condensation of 2,4-diamino-6-(bromomethyl)pteridine with diethyl N-(p-aminobenzyl)-L-glutamate, followed by saponification with a stoichiometric amount of barium hydroxide in 50% ethanol. The apparent importance of the amide C = O group as a structural determinant of biological activity was indicated by the finding that 1 has 10- to 20-fold lower affinity for bacterial and mammalian dihydrofolate reductase than aminopterin, is not toxic to L1210 murine leukemia cells in culture at a concentration of up to 1.0 microM, and shows no antitumor effect in L1210 leukemic mice at doses as high as 240 mg/kg (q3d X 3).

  DOI：

  10.1021/jm00354a013
• 作为产物：
  描述：

  谷氨酸二乙酯 在 palladium on activated charcoal sodium tetrahydroborate 、 4 A molecular sieve 、 氢气 作用下， 以 苯 为溶剂， 反应 3.25h， 生成 diethyl N-(p-aminobenzyl)-L-glutamate
  参考文献：
  名称：

  Methotrexate analogs. 16. Importance of the side-chain amide carbonyl group as a structural determinant of biological activity

  摘要：

  N-[[[(2,4-Diaminopteridin-6-yl)methyl]amino]benzyl]-L-glutamic acid ("deoxoaminopterin", 1), a new aminopterin analogue containing a CH2 group in the side chain in place of the amide C = O, was synthesized by condensation of 2,4-diamino-6-(bromomethyl)pteridine with diethyl N-(p-aminobenzyl)-L-glutamate, followed by saponification with a stoichiometric amount of barium hydroxide in 50% ethanol. The apparent importance of the amide C = O group as a structural determinant of biological activity was indicated by the finding that 1 has 10- to 20-fold lower affinity for bacterial and mammalian dihydrofolate reductase than aminopterin, is not toxic to L1210 murine leukemia cells in culture at a concentration of up to 1.0 microM, and shows no antitumor effect in L1210 leukemic mice at doses as high as 240 mg/kg (q3d X 3).

  DOI：

  10.1021/jm00354a013

文献信息

• Methotrexate analogs. 16. Importance of the side-chain amide carbonyl group as a structural determinant of biological activity
  作者：A. Rosowsky、R. Forsch

  DOI：10.1021/jm00354a013

  日期：1982.12

  N-[[[(2,4-Diaminopteridin-6-yl)methyl]amino]benzyl]-L-glutamic acid ("deoxoaminopterin", 1), a new aminopterin analogue containing a CH2 group in the side chain in place of the amide C = O, was synthesized by condensation of 2,4-diamino-6-(bromomethyl)pteridine with diethyl N-(p-aminobenzyl)-L-glutamate, followed by saponification with a stoichiometric amount of barium hydroxide in 50% ethanol. The apparent importance of the amide C = O group as a structural determinant of biological activity was indicated by the finding that 1 has 10- to 20-fold lower affinity for bacterial and mammalian dihydrofolate reductase than aminopterin, is not toxic to L1210 murine leukemia cells in culture at a concentration of up to 1.0 microM, and shows no antitumor effect in L1210 leukemic mice at doses as high as 240 mg/kg (q3d X 3).