N-[3-[1-(1,2,3,4-tetrahydro)quinolinyl]sulfonylphenyl]-3-(2-naphthyl)acrylic acid amide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-[3-[1-(1,2,3,4-tetrahydro)quinolinyl]sulfonylphenyl]-3-(2-naphthyl)acrylic acid amide
• 英文别名: (E)-N-[3-(3,4-dihydro-2H-quinolin-1-ylsulfonyl)phenyl]-3-naphthalen-2-ylprop-2-enamide
• 化学式: C₂₈H₂₄N₂O₃S
• 分子量: 468.576
• InChiKey: VYXYXEQVFUSDBZ-BMRADRMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-3-(萘-2-基)丙烯酸 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 N-[3-[1-(1,2,3,4-tetrahydro)quinolinyl]sulfonylphenyl]-3-(2-naphthyl)acrylic acid amide
  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

文献信息

• Non-Thiol Farnesyltransferase Inhibitors: Evaluation of Different AA(X)-Peptidomimetic Substructures in Combination with Arylic Cysteine Replacements
  作者：Jacek Sakowski、Markus Böhm、Isabel Sattler、Martin Schlitzer

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

  日期：2002.4

  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).