methyl (2S)-4-methylsulfanyl-2-[[4-[[(E)-3-[5-(4-nitrophenyl)furan-2-yl]prop-2-enoyl]amino]benzoyl]amino]butanoate | 875119-71-4

• 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: methyl (2S)-4-methylsulfanyl-2-[[4-[[(E)-3-[5-(4-nitrophenyl)furan-2-yl]prop-2-enoyl]amino]benzoyl]amino]butanoate
• CAS: 875119-71-4
• 化学式: C₂₆H₂₅N₃O₇S
• 分子量: 523.566
• InChiKey: FEYGNZKDQGZWSL-VKXNWWILSA-N

物化性质

• 沸点：
  801.4±65.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  169
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (2S)-4-methylsulfanyl-2-[[4-[[(E)-3-[5-(4-nitrophenyl)furan-2-yl]prop-2-enoyl]amino]benzoyl]amino]butanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以72%的产率得到(2S)-4-methylsulfanyl-2-[[4-[[(E)-3-[5-(4-nitrophenyl)furan-2-yl]prop-2-enoyl]amino]benzoyl]amino]butanoic acid
  参考文献：
  名称：

  Non-Thiol Farnesyltransferase Inhibitors: Evaluation of Different AA(X)-Peptidomimetic Substructures in Combination with Arylic Cysteine Replacements

  摘要：

  In the course of our studies on non-thiol farnesyltransferase inhibitors based on the 2,5-diaminobenzophenone AAX-peptidomimetic substructure, we have developed the (4-nitrophenyl)butyryl (R-1), the (2-naphthyl)acryloyl (R-2), the 4-nitrocinnamoyl (R-3), and the 5-(4-nitrophenyl)furylacryloyl (R-4) groups as useful cysteine replacements. In this study, we combined these four groups with other AA(X)-peptidomimetic substructures (5-10: R = H) reported in the literature. The 5-(4-nitrophenyl)furylacryloyl moiety (R-4) turned out to be the most useful non-thiol cysteine replacement yielding in all cases the most active inhibitors. By combination of this 5-(4-nitrophenyl)furylacryloyl moiety (R 4) with the structurally simple AAX-peptidomimetics 4-aminobenzophenone (5) and 4-aminodiphenylsulfone (6) potent, readily accessible non-thiol farnesyltransferase inhibitors were obtained (IC50 = 12 nM and 10 nM).

  DOI：

  10.1002/1521-4184(200204)335:4<135::aid-ardp135>3.0.co;2-7
• 作为产物：
  描述：

  3-<5-(4-Nitrophenyl)-2-furyl>propenoic acid 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 methyl (2S)-4-methylsulfanyl-2-[[4-[[(E)-3-[5-(4-nitrophenyl)furan-2-yl]prop-2-enoyl]amino]benzoyl]amino]butanoate
  参考文献：
  名称：

  Non-Thiol Farnesyltransferase Inhibitors: Evaluation of Different AA(X)-Peptidomimetic Substructures in Combination with Arylic Cysteine Replacements

  摘要：

  In the course of our studies on non-thiol farnesyltransferase inhibitors based on the 2,5-diaminobenzophenone AAX-peptidomimetic substructure, we have developed the (4-nitrophenyl)butyryl (R-1), the (2-naphthyl)acryloyl (R-2), the 4-nitrocinnamoyl (R-3), and the 5-(4-nitrophenyl)furylacryloyl (R-4) groups as useful cysteine replacements. In this study, we combined these four groups with other AA(X)-peptidomimetic substructures (5-10: R = H) reported in the literature. The 5-(4-nitrophenyl)furylacryloyl moiety (R-4) turned out to be the most useful non-thiol cysteine replacement yielding in all cases the most active inhibitors. By combination of this 5-(4-nitrophenyl)furylacryloyl moiety (R 4) with the structurally simple AAX-peptidomimetics 4-aminobenzophenone (5) and 4-aminodiphenylsulfone (6) potent, readily accessible non-thiol farnesyltransferase inhibitors were obtained (IC50 = 12 nM and 10 nM).

  DOI：

  10.1002/1521-4184(200204)335:4<135::aid-ardp135>3.0.co;2-7