A fruitful century for the scalable synthesis and reactions of biphenyl derivatives: applications and biological aspects

被引:13
作者
Ali, Hajar A. [1 ]
Ismail, Mohamed A. [1 ]
Fouda, Abd El-Aziz S. [1 ]
Ghaith, Eslam A. [1 ]
机构
[1] Mansoura Univ, Fac Sci, Chem Dept, Mansoura 35516, Egypt
关键词
CROSS-COUPLING REACTION; FRIEDEL-CRAFTS ACYLATION; C-H AMINATION; PALLADIUM-CATALYZED REACTION; CARBON BOND FORMATION; AROMATIC-COMPOUNDS; LEWIS-ACID; CLINICAL PHARMACOKINETICS; ORGANOMETALLIC COMPOUNDS; TORSIONAL BARRIERS;
D O I
10.1039/d3ra03531j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This review provides recent developments in the current status and latest synthetic methodologies of biphenyl derivatives. Furthermore, this review investigates detailed discussions of several metalated chemical reactions related to biphenyl scaffolds such as Wurtz-Fittig, Ullmann, Bennett-Turner, Negishi, Kumada, Stille, Suzuki-Miyaura, Friedel-Crafts, cyanation, amination, and various electrophilic substitution reactions supported by their mechanistic pathways. Furthermore, the preconditions required for the existence of axial chirality in biaryl compounds are discussed. Furthermore, atropisomerism as a type of axial chirality in biphenyl molecules is discussed. Additionally, this review covers a wide range of biological and medicinal applications of the synthesized compounds involving patented approaches in the last decade corresponding to investigating the crucial role of the biphenyl structures in APIs.
引用
收藏
页码:18262 / 18305
页数:44
相关论文
共 221 条
[1]   Discovery of new cholesteryl ester transfer protein inhibitors via ligand-based pharmacophore modeling and QSAR analysis followed by synthetic exploration [J].
Abu Khalaf, Reema ;
Abu Sheikha, Ghassan ;
Bustanji, Yasser ;
Taha, Mutasem O. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (04) :1598-1617
[2]   A Copper(I)-Catalyzed Sulfonylative Hiyama Cross-Coupling [J].
Adenot, Aurelien ;
Anthore-Dalion, Lucile ;
Nicolas, Emmanuel ;
Berthet, Jean-Claude ;
Thuery, Pierre ;
Cantat, Thibault .
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (72) :18047-18053
[3]   Synthesis of biphenyl oxazole derivatives via Suzuki coupling and biological evaluations as nucleotide pyrophosphatase/phosphodiesterase-1 and-3 inhibitors [J].
Ahmad, Haseen ;
Ullah, Saif ;
Rahman, Fouzia ;
Saeed, Aamer ;
Pelletier, Julie ;
Sevigny, Jean ;
Hassan, Abbas ;
Iqbal, Jamshed .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2020, 208
[4]   Aerobic Copper-Catalyzed Organic Reactions [J].
Allen, Scott E. ;
Walvoord, Ryan R. ;
Padilla-Salinas, Rosaura ;
Kozlowski, Marisa C. .
CHEMICAL REVIEWS, 2013, 113 (08) :6234-6458
[5]   Site-selective Suzuki-Miyaura coupling of heteroaryl halides - understanding the trends for pharmaceutically important classes [J].
Almond-Thynne, Joshua ;
Blakemore, David C. ;
Pryde, David C. ;
Spivey, Alan C. .
CHEMICAL SCIENCE, 2017, 8 (01) :40-62
[6]   Mechanism of Palladium-Catalyzed Suzuki-Miyaura Reactions: Multiple and Antagonistic Roles of Anionic "Bases" and Their Countercations [J].
Amatore, Christian ;
Le Duc, Gaetan ;
Jutand, Anny .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (31) :10082-10093
[7]  
[Anonymous], 2018, Palladium-Catalyzed Modification of Nucleosides, Nucleotides and Oligonucleotides
[8]   Copper catalysed Gomberg-Bachmann-Hey reactions of arenediazonium tetrafluoroborates and heteroarenediazonium o-benzenedisulfonimides. Synthetic and mechanistic aspects [J].
Antenucci, Achille ;
Barbero, Margherita ;
Dughera, Stefano ;
Ghigo, Giovanni .
TETRAHEDRON, 2020, 76 (47)
[9]   Halogen-sodium exchange enables efficient access to organosodium compounds [J].
Asako, Sobi ;
Takahashi, Ikko ;
Nakajima, Hirotaka ;
Ilies, Laurean ;
Takai, Kazuhiko .
COMMUNICATIONS CHEMISTRY, 2021, 4 (01)
[10]   Cobalt-Catalyzed Suzuki Biaryl Coupling of Aryl Halides [J].
Asghar, Soneela ;
Tailor, Sanita B. ;
Elorriaga, David ;
Bedford, Robin B. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (51) :16367-16370