(4E,8E)-2-[Benzenesulfonyl-(3-methyl-3H-imidazol-4-ylmethyl)-amino]-5,9,13-trimethyl-tetradeca-4,8,12-trienoic acid | 565469-65-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4E,8E)-2-[Benzenesulfonyl-(3-methyl-3H-imidazol-4-ylmethyl)-amino]-5,9,13-trimethyl-tetradeca-4,8,12-trienoic acid
• CAS: 565469-65-0
• 化学式: C₂₈H₃₉N₃O₄S
• 分子量: 513.701
• InChiKey: LQZHXGXDGXIXGP-URGZSASVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  36.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  92.5
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4E,8E)-2-[Benzenesulfonyl-(3-methyl-3H-imidazol-4-ylmethyl)-amino]-5,9,13-trimethyl-tetradeca-4,8,12-trienoic acid 在 lithium hydroxide 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-2-{(4E,8E)-2-[Benzenesulfonyl-(3-methyl-3H-imidazol-4-ylmethyl)-amino]-5,9,13-trimethyl-tetradeca-4,8,12-trienoylamino}-3-phenyl-propionic acid
  参考文献：
  名称：

  From pure FPP to mixed FPP and CAAX competitive inhibitors of farnesyl protein transferase

  摘要：

  Starting from a FPP analogue with nanomolar inhibitory activity against isolated FPTase, yet lacking activity in cellular assays, structural modifications were performed to enhance cellular activity by removing all acidic functionalities. Overall, these changes resulted in the transformation of a pure FPP to a mixed FPP and CAAX competitive inhibitor with nanomolar activity on isolated FPTase and micromolar inhibitory activity in the farnesylation of H-Ras in cultured DLD-1 cells. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00171-9
• 作为产物：
  描述：

  在 吡啶 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (4E,8E)-2-[Benzenesulfonyl-(3-methyl-3H-imidazol-4-ylmethyl)-amino]-5,9,13-trimethyl-tetradeca-4,8,12-trienoic acid
  参考文献：
  名称：

  From pure FPP to mixed FPP and CAAX competitive inhibitors of farnesyl protein transferase

  摘要：

  Starting from a FPP analogue with nanomolar inhibitory activity against isolated FPTase, yet lacking activity in cellular assays, structural modifications were performed to enhance cellular activity by removing all acidic functionalities. Overall, these changes resulted in the transformation of a pure FPP to a mixed FPP and CAAX competitive inhibitor with nanomolar activity on isolated FPTase and micromolar inhibitory activity in the farnesylation of H-Ras in cultured DLD-1 cells. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00171-9