8-deaza-10-propargylfolic acid | 106500-88-3

• 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: 8-deaza-10-propargylfolic acid
• 英文别名: (2S)-2-[[4-[(2-amino-4-oxo-3H-pyrido[3,2-d]pyrimidin-6-yl)methyl-prop-2-ynylamino]benzoyl]amino]pentanedioic acid
• CAS: 106500-88-3
• 化学式: C₂₃H₂₂N₆O₆
• 分子量: 478.464
• InChiKey: XRGFEWIERJRPFJ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  187
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  diethyl N-(4-(prop-2-ynylamino)benzoyl)-L-glutamate 在 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 50.0h， 生成 8-deaza-10-propargylfolic acid
  参考文献：
  名称：

  Folate analogs as inhibitors of thymidylate synthase

  摘要：

  Recent demonstrations that deazafolate analogues may act as potent inhibitors of thymidylate synthase (TS) provided a firm rationale for the synthesis of N10-propargyl derivatives of 8-deazafolate and 8-deazaaminopterin (4). A complete assignment of the 1H NMR spectra of these compounds was made possible through application of 2D (COSY) techniques at 200 MHz. Data describing the inhibition of TS derived from human leukemia (K562) cells are presented. IC50 values of 2.25 and 1.26 microM were determined for 8-deaza-10-propargylfolate (3) and 8-deaza-10-propargylaminopterin, respectively. Comparison of the data for various folate analogues reveals a striking dependence of TS inhibitory potency upon the number of nitrogens in the folate pyrazine ring.

  DOI：

  10.1021/jm00387a016

文献信息

• Folate analogs as inhibitors of thymidylate synthase
  作者：Diana I. Brixner、Takamori Ueda、Yung Chi Cheng、John B. Hynes、Arthur D. Broom

  DOI：10.1021/jm00387a016

  日期：1987.4

  Recent demonstrations that deazafolate analogues may act as potent inhibitors of thymidylate synthase (TS) provided a firm rationale for the synthesis of N10-propargyl derivatives of 8-deazafolate and 8-deazaaminopterin (4). A complete assignment of the 1H NMR spectra of these compounds was made possible through application of 2D (COSY) techniques at 200 MHz. Data describing the inhibition of TS derived from human leukemia (K562) cells are presented. IC50 values of 2.25 and 1.26 microM were determined for 8-deaza-10-propargylfolate (3) and 8-deaza-10-propargylaminopterin, respectively. Comparison of the data for various folate analogues reveals a striking dependence of TS inhibitory potency upon the number of nitrogens in the folate pyrazine ring.