2-phenyl-4-nitro-3'-methoxycarbonylbiphenyl | 323191-84-0

• 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-nitro-3'-methoxycarbonylbiphenyl
• 英文别名: 4-nitro-2-phenyl-3'-methoxycarbonylbiphenyl；Methyl 3-(4-nitro-2-phenylphenyl)benzoate；methyl 3-(4-nitro-2-phenylphenyl)benzoate
• CAS: 323191-84-0
• 化学式: C₂₀H₁₅NO₄
• 分子量: 333.343
• InChiKey: XGHVNYRRWAZOIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-nitro-3'-methoxycarbonylbiphenyl 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2-phenyl-4-nitro-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
• 作为产物：
  描述：

  甲醇 、 2-phenyl-4-nitro-3'-carboxybiphenyl 在 氯化亚砜 作用下， 反应 5.0h， 以1.20 g的产率得到2-phenyl-4-nitro-3'-methoxycarbonylbiphenyl
  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

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.
• Development of a Tripeptide Mimetic Strategy for the Inhibition of Protein Farnesyltransferase
  作者：Mohit A. Kotharé、Junko Ohkanda、Jeffrey W. Lockman、Yimin Qian、Michelle A. Blaskovich、Said M. Sebti、Andrew D. Hamilton

  DOI：10.1016/s0040-4020(00)00890-5

  日期：2000.12

  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.