(2S,3S)-2-Amino-3-methyl-pentanoic acid 5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pentyl ester | 792909-73-0

• 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: (2S,3S)-2-Amino-3-methyl-pentanoic acid 5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pentyl ester
• CAS: 792909-73-0
• 化学式: C₁₅H₂₄FN₃O₄
• 分子量: 329.372
• InChiKey: NKQYDKRVNHAINY-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  23.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  107.18
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4'-O-demethyl-4β-bromo-4-desoxypodophyllotoxin 、 (2S,3S)-2-Amino-3-methyl-pentanoic acid 5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pentyl ester 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S)-2-[(5S,5aS,8aR,9R)-9-(4-Hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-ylamino]-3-methyl-pentanoic acid 5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pentyl ester
  参考文献：
  名称：

  Synthesis and cytotoxic activity of novel derivatives of 4′-demethylepipodophyllotoxin

  摘要：

  Nine novel 4beta-N-substituted-5-FU-4'-demethylepipodophyllotoxin derivatives were synthesized and evaluated as potential antitumor agents. All of the target compounds showed more significant cytotoxic activity against HL-60 and A-549 in vitro than VP-16 and 5-FU. Among them, 4beta-N-substituted-phenylalanine 5-Fu pentyl ester-4'-demethylepipodophyllotoxin (9g) was found to exhibit most potent cytotoxic activity against HL-60 and A-549 cell (IC50 is 0.04 and <0.01 muM, respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.094
• 作为产物：
  描述：

  Potassium; (2S,3S)-2-amino-3-methyl-pentanoate 在 盐酸 、 potassium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3S)-2-Amino-3-methyl-pentanoic acid 5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pentyl ester
  参考文献：
  名称：

  Synthesis and cytotoxic activity of novel derivatives of 4′-demethylepipodophyllotoxin

  摘要：

  Nine novel 4beta-N-substituted-5-FU-4'-demethylepipodophyllotoxin derivatives were synthesized and evaluated as potential antitumor agents. All of the target compounds showed more significant cytotoxic activity against HL-60 and A-549 in vitro than VP-16 and 5-FU. Among them, 4beta-N-substituted-phenylalanine 5-Fu pentyl ester-4'-demethylepipodophyllotoxin (9g) was found to exhibit most potent cytotoxic activity against HL-60 and A-549 cell (IC50 is 0.04 and <0.01 muM, respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.094