2-phenyl-4-[3-S-(tert-butoxycarbonyl)mercaptobenzoyl]amino-3'-carboxybiphenyl | 323191-91-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenyl-4-[3-S-(tert-butoxycarbonyl)mercaptobenzoyl]amino-3'-carboxybiphenyl
• CAS: 323191-91-9
• 化学式: C₃₁H₂₇NO₅S
• 分子量: 525.625
• InChiKey: HSVJJSVATPXABJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.0
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  92.7
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-[3-S-(tert-butoxycarbonyl)mercaptobenzoyl]amino-3'-carboxybiphenyl 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到FTI-2313
  参考文献：
  名称：

  Development of a Tripeptide Mimetic Strategy for the Inhibition of Protein Farnesyltransferase

  摘要：

  This paper describes the development of a novel terphenyl-based tripeptide mimetic of the CAAX carboxy terminal sequence of Ras. We employ a concise synthesis to form a series of differently functionalized terphenyl inhibitors of protein farnesyltransferase (PFTase), exemplified by 5, 6 and 7. The key reaction in the synthesis of the terphenyl methyl ester 13, and therefore 6 and 7, was the Pd-catalyzed chemoselective Suzuki cross-coupling of 3-bromo-4-chloronitrobenzene 16 with an appropriate boronic acid derivative utilizing a commercially available, electron rich phosphine Ligand. We further show that one member of this series is a potent inhibitor of PFTase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00890-5
• 作为产物：
  描述：

  2-phenyl-4-nitro-3'-methylbiphenyl 在 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 2-phenyl-4-[3-S-(tert-butoxycarbonyl)mercaptobenzoyl]amino-3'-carboxybiphenyl
  参考文献：
  名称：

  Development of a Tripeptide Mimetic Strategy for the Inhibition of Protein Farnesyltransferase

  摘要：

  This paper describes the development of a novel terphenyl-based tripeptide mimetic of the CAAX carboxy terminal sequence of Ras. We employ a concise synthesis to form a series of differently functionalized terphenyl inhibitors of protein farnesyltransferase (PFTase), exemplified by 5, 6 and 7. The key reaction in the synthesis of the terphenyl methyl ester 13, and therefore 6 and 7, was the Pd-catalyzed chemoselective Suzuki cross-coupling of 3-bromo-4-chloronitrobenzene 16 with an appropriate boronic acid derivative utilizing a commercially available, electron rich phosphine Ligand. We further show that one member of this series is a potent inhibitor of PFTase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00890-5