N-1-(4-chlorophenyl)cyclopentanecarbonyl-L-cysteine[S-(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]-OH | 1144114-35-1

• 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: N-1-(4-chlorophenyl)cyclopentanecarbonyl-L-cysteine[S-(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]-OH
• 英文别名: (2R)-2-[[1-(4-chlorophenyl)cyclopentanecarbonyl]amino]-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]sulfanylpropanoic acid
• CAS: 1144114-35-1
• 化学式: C₃₀H₄₂ClNO₃S
• 分子量: 532.187
• InChiKey: CUIURVNQCBYXAO-ATEQNONDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2R)-2-[[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carbonyl]amino]-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]sulfanylpropanoic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.1h， 生成 N-1-(4-chlorophenyl)cyclopentanecarbonyl-L-cysteine[S-(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]-OH
  参考文献：
  名称：

  Solid-Phase Synthesis of Prenylcysteine Analogs

  摘要：

  [GRAPHICS]Prenylcysteine derivatives are of interest for a variety of different biological reasons, including probing the CaaX protein processing pathway. A solid-phase synthesis protocol for the preparation of prenylcysteines using 2-chlorotrityl chloride resin as a solid support has been developed. A series of novel amide-modified farnesylcysteine analogs were synthesized in both high purity and yield under mild conditions. The farnesylcysteine analogs were evaluated using human isoprenylcysteine carboxyl methyltransferase as a biological target, and several new inhibitors, one with significantly enhanced potency, were identified.

  DOI：

  10.1021/jo8021692