A Simple and Effective Synthesis of 3- and 4-((Phenylcarbamoyl)oxy)benzoic Acids

Abstract

Phenserine, posiphen, tolserine and cymserine and its derivatives are experimental Alzheimer's disease drugs that contain a phenyl phenylcarbamate moiety that is responsible for their anti-Alzheimer activities. We have developed a simple (3 steps) and effective (overall yields 76-90%) method for preparing 3-and 4-((phenylcarbamoyl)oxy)benzoic acids which can be reacted with amines to produce phenyl phenylcarbamate moiety containing amides as new potential anti-Alzheimer disease drugs. The synthesized carboxylic acids are thus important building blocks with potential use in medicinal chemistry and drug discovery.

Synthesis, crystal structure, DFT calculation and Hirshfeld surface analysis of N-(4-methyl phenyl)-2-(3-nitro-benzamido) benzamide

“…The amide 2-(3-nitrobenzamido)-N-(p-tolyl) benzamide was formed from ring opening reaction of 2-(3-nitrophenyl)-4H-benzo [1,3]oxazin-4-one with 4-methyl aniline. The structure of newly synthesized compounds was investigated by FT-IR, 1 H-NMR and 13 C-NMR.…”

“…The synthesis of the titled compound as in (Scheme 1) was synthesized by the reaction of ptoluidine (321.21 mg, 3.00 mmol) with 2-(3-nitrophenyl)-4H-benzo- [1,3]oxazin-4-one (804.8 mg, 3.00 mmol) in glacial acetic acid (12 mL). It was heated, the solid product was collected within one minute [11].…”

“…It serves as a primary linker in peptides and several polymers. Amides are a diverse category of bioactive components that are present in plants and thus are crucial including both their growth and defence against environmental triggers [3][4][5].…”