硫酸,O-(1,1-二甲基乙基)S-(4-甲酰基苯基)酯 | 396725-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 硫酸,O-(1,1-二甲基乙基)S-(4-甲酰基苯基)酯
• 英文名称: 4-S-(t-butoxycarbonyl)mercaptobenzaldehyde
• 英文别名: thiocarbonic acid o-tert-butyl ester S-(4-formyl-phenyl) ester；tert-butyl (4-formylphenyl)sulfanylformate
• CAS: 396725-68-1
• 化学式: C₁₂H₁₄O₃S
• 分子量: 238.307
• InChiKey: AANXOPGCFWCAFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  硫酸,O-(1,1-二甲基乙基)S-(4-甲酰基苯基)酯 在 sodium tetrahydroborate 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 FTI-2342
  参考文献：
  名称：

  Design and Synthesis of Potent Nonpeptidic Farnesyltransferase Inhibitors Based on a Terphenyl Scaffold

  摘要：

  By modification of key carboxylate, hydrophobic, and zinc-binding groups projected from a sterically restricted terphenyl scaffold, a series of simple and nonpeptide mimetics of the Cys-Val-Ile-Met tetrapeptide substrate of protein farnesyltransferase (FTase) have been designed and synthesized. A crystal structure of 4-nitro-2-phenyl-3'-methoxycarbonylbiphenyl shows that the triphenyl fragment provides a large hydrophobic surface that potentially mimics the hydrophobic side chains of the three terminal residues in the tetrapeptide. 2-Phenyl-3-(N-(1-(4-eyanobenzyl)-1H-imidazol-5-yl)methyl)amino-3'carboxylbiphenyl, in which the free thiol group was replaced with a 1-(4-cyanobenzyl)imidazole group, shows submicromolar inhibition activity against FTase in vitro and inhibits H-Ras processing in whole cells.

  DOI：

  10.1021/jm0103099
• 作为产物：
  描述：

  4-S-(t-butoxycarbonyl)mercaptobenzoic acid 在 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 硫酸,O-(1,1-二甲基乙基)S-(4-甲酰基苯基)酯
  参考文献：
  名称：

  Design and Synthesis of Potent Nonpeptidic Farnesyltransferase Inhibitors Based on a Terphenyl Scaffold

  摘要：

  By modification of key carboxylate, hydrophobic, and zinc-binding groups projected from a sterically restricted terphenyl scaffold, a series of simple and nonpeptide mimetics of the Cys-Val-Ile-Met tetrapeptide substrate of protein farnesyltransferase (FTase) have been designed and synthesized. A crystal structure of 4-nitro-2-phenyl-3'-methoxycarbonylbiphenyl shows that the triphenyl fragment provides a large hydrophobic surface that potentially mimics the hydrophobic side chains of the three terminal residues in the tetrapeptide. 2-Phenyl-3-(N-(1-(4-eyanobenzyl)-1H-imidazol-5-yl)methyl)amino-3'carboxylbiphenyl, in which the free thiol group was replaced with a 1-(4-cyanobenzyl)imidazole group, shows submicromolar inhibition activity against FTase in vitro and inhibits H-Ras processing in whole cells.

  DOI：

  10.1021/jm0103099

文献信息

• Design and Synthesis of Potent Nonpeptidic Farnesyltransferase Inhibitors Based on a Terphenyl Scaffold
  作者：Junko Ohkanda、Jeffrey W. Lockman、Mohit A. Kothare、Yimin Qian、Michelle A. Blaskovich、Said M. Sebti、Andrew D. Hamilton

  DOI：10.1021/jm0103099

  日期：2002.1.1

  By modification of key carboxylate, hydrophobic, and zinc-binding groups projected from a sterically restricted terphenyl scaffold, a series of simple and nonpeptide mimetics of the Cys-Val-Ile-Met tetrapeptide substrate of protein farnesyltransferase (FTase) have been designed and synthesized. A crystal structure of 4-nitro-2-phenyl-3'-methoxycarbonylbiphenyl shows that the triphenyl fragment provides a large hydrophobic surface that potentially mimics the hydrophobic side chains of the three terminal residues in the tetrapeptide. 2-Phenyl-3-(N-(1-(4-eyanobenzyl)-1H-imidazol-5-yl)methyl)amino-3'carboxylbiphenyl, in which the free thiol group was replaced with a 1-(4-cyanobenzyl)imidazole group, shows submicromolar inhibition activity against FTase in vitro and inhibits H-Ras processing in whole cells.