diethyl (2S)-2-[[4-[2-[(2-amino-6-methyl-4-oxo-1H-pyrimidin-5-yl)amino]ethylamino]benzoyl]amino]pentanedioate | 107716-33-6

• 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 (2S)-2-[[4-[2-[(2-amino-6-methyl-4-oxo-1H-pyrimidin-5-yl)amino]ethylamino]benzoyl]amino]pentanedioate
• CAS: 107716-33-6
• 化学式: C₂₃H₃₂N₆O₆
• 分子量: 488.544
• InChiKey: XRTANUAVZZSVFR-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  35.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  177.53
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  diethyl (2S)-2-[[4-[2-[(2-amino-6-methyl-4-oxo-1H-pyrimidin-5-yl)amino]ethylamino]benzoyl]amino]pentanedioate 在 sodium hydroxide 、 铜 、 碳酸氢钠 、 乙酰丙酮 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 51.5h， 生成 N-<4-amino>ethyl>amino>benzoyl>-L-glutamic acid 5'-monophosphate
  参考文献：
  名称：

  A pyrimidine-based "flexible" bisubstrate analog inhibitor of human thymidylate synthase

  摘要：

  The synthesis and characterization of two "flexible" bisubstrate analogues of the intermediate in the thymidylate synthase reaction are reported. Steric constraints are minimized and diasteromeric mixtures avoided by using a pyrimidine-based analogue as the folate portion of the inhibitor while retaining all known important binding sites. A preliminary assessment of certain conformational parameters by NMR is presented. The compounds are shown to be potent competitive inhibitors with respect to dUMP or 5,10-CH2-H4PteGlu but gave mixed kinetics with respect to 5,10-CH2-H4PteGlu5 for human thymidylate synthase.

  DOI：

  10.1021/jm00119a012
• 作为产物：
  描述：

  N-(4-氨基苯(甲)酰)-L-谷氨酸二乙酯 在 氢溴酸 、 苯酚 作用下， 以 吡啶 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.5h， 生成 diethyl (2S)-2-[[4-[2-[(2-amino-6-methyl-4-oxo-1H-pyrimidin-5-yl)amino]ethylamino]benzoyl]amino]pentanedioate
  参考文献：
  名称：

  A pyrimidine-based "flexible" bisubstrate analog inhibitor of human thymidylate synthase

  摘要：

  The synthesis and characterization of two "flexible" bisubstrate analogues of the intermediate in the thymidylate synthase reaction are reported. Steric constraints are minimized and diasteromeric mixtures avoided by using a pyrimidine-based analogue as the folate portion of the inhibitor while retaining all known important binding sites. A preliminary assessment of certain conformational parameters by NMR is presented. The compounds are shown to be potent competitive inhibitors with respect to dUMP or 5,10-CH2-H4PteGlu but gave mixed kinetics with respect to 5,10-CH2-H4PteGlu5 for human thymidylate synthase.

  DOI：

  10.1021/jm00119a012

文献信息

• YANG, IN-YOUNG;SLUSHER, R. MARK;BROOM, ARTHUR D.;UEDA, T.;CHENG, YUNG-CHI, J. MED. CHEM., 31,(1988) N 11, C. 2126-2132
  作者：YANG, IN-YOUNG、SLUSHER, R. MARK、BROOM, ARTHUR D.、UEDA, T.、CHENG, YUNG-CHI

  DOI：——

  日期：——