Phenoxyalkyl cyclic and acyclic amine derivatives: what do they teach us about scaffold-based drug design?

Rezaeifar, Mohammad Mahdi; Abiri, Ardavan; Rezaiezadeh, Hojjat; Tavakoli, Marziye Ranjbar; Langarizadeh, Mohammad Amin; Pourshojaei, Yaghoub

doi:10.1007/s00044-024-03215-1

Med Chem Res

2024

DOI: 10.1007/s00044-024-03215-1

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Phenoxyalkyl cyclic and acyclic amine derivatives: what do they teach us about scaffold-based drug design?

Mohammad Mahdi Rezaeifar,

Ardavan Abiri,

Hojjat Rezaiezadeh

et al.

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Cited by 2 publications

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Nickel‐Catalyzed O‐Arylation of N‐Protected Amino Alcohols with (Hetero)aryl Chlorides

Morrison,

Jackson,

Elliott

et al. 2024

Chemistry A European J

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The aryloxyamine motif is a prominent pharmacophore in drug design and development. While these biologically relevant structures could in principle be sustainably assembled from the base metal‐catalyzed O‐arylation of inexpensive and abundant amino alcohols with (hetero)aryl chlorides, reports of such challenging C–O bond formations with useful scope are lacking. In response, we report herein the hitherto unknown Ni‐catalyzed C–O cross‐coupling of N‐protected amino alcohols (primary, secondary, and tertiary) with (hetero)aryl chlorides. Also presented are chemoselective sequential/telescoped C–N and C–O cross‐couplings of the unprotected amino alcohol prolinol to afford an unsymmetrical diarylated product.

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Nickel‐Catalyzed O‐Arylation of N‐Protected Amino Alcohols with (Hetero)aryl Chlorides

Morrison,

Jackson,

Elliott

et al. 2024

Chemistry A European J

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Progress in Enzyme-Catalyzed C(sp³)–H Amination

Xu,

Gao,

et al. 2024

ACS Catal.

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Amine structures are widely present in various biologically active natural products, drug molecules, and material structures. Among the various strategies of amine synthesis, C(sp 3 )−H amination has become a powerful strategy due to its atom economy and multiple potential reaction sites compared with conventional amine synthesis methods. Due to the advantages of high catalytic efficiency, high selectivity, environmental friendliness, and high modifiability of the enzyme, the enzymatic C(sp 3 )−H amination is of great research significance. However, it was not until recent years that natural enzymes capable of catalyzing the amination of C(sp 3 )−H bonds were discovered. Modifying enzymes to confer unnatural C(sp 3 )−H amination activity holds great potential. In the past decade, a series of protocols for the amination of C(sp 3 )−H bonds using engineered enzymes have been developed, several of which showed comparable properties to those of natural enzymes.

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Phenoxyalkyl cyclic and acyclic amine derivatives: what do they teach us about scaffold-based drug design?

Cited by 2 publications

References 124 publications

Nickel‐Catalyzed O‐Arylation of N‐Protected Amino Alcohols with (Hetero)aryl Chlorides

Nickel‐Catalyzed O‐Arylation of N‐Protected Amino Alcohols with (Hetero)aryl Chlorides

Progress in Enzyme-Catalyzed C(sp³)–H Amination

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Phenoxyalkyl cyclic and acyclic amine derivatives: what do they teach us about scaffold-based drug design?

Cited by 2 publications

References 124 publications

Nickel‐Catalyzed O‐Arylation of N‐Protected Amino Alcohols with (Hetero)aryl Chlorides

Nickel‐Catalyzed O‐Arylation of N‐Protected Amino Alcohols with (Hetero)aryl Chlorides

Progress in Enzyme-Catalyzed C(sp3)–H Amination

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Product

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About

Progress in Enzyme-Catalyzed C(sp³)–H Amination