Synthesis of phenylcarbamate derivatives using amino acids and study of their effects on the morphology of pheochromocytoma cells (PC12)

Subject Areas :

mahshid nikpour nezhati ¹ , gholamhossein riazi ² , safiyeh sadat gholestaneh far ³ , fatemeh sadat hosseini rostami ⁴ , hamid mohammad hosseini ⁵ , samaneh gholestani ⁶

1 - استادیار شیمی آلی، دانشکده علوم پایه، واحد تهران مرکزی، دانشگاه آزاد اسلامی، تهران، ایران
2 - استاد بیوشیمی، مرکز تحقیقات بیوشیمی و بیوفیزیک، دانشگاه تهران، تهران، ایران
3 - کارشناسی ارشد شیمی آلی، دانشکده علوم پایه، واحد تهران مرکزی، دانشگاه آزاد اسلامی، تهران، ایران
4 - کارشناسی ارشد شیمی آلی، دانشکده علوم پایه، واحد تهران مرکزی، دانشگاه آزاد اسلامی، تهران، ایران
5 - کارشناسی ارشد شیمی آلی، دانشکده علوم پایه، واحد تهران مرکزی، دانشگاه آزاد اسلامی، تهران، ایران
6 - M.Sc. of Organic Chemistry, Dempartment of Chemistry, Centeral Tehran Branch, Islamic Azad University, Tehran, Iran.

Received: 2021-02-20 Accepted : 2021-02-20 Published : 2021-02-19

Keywords: isoleucine, Phenylcarbamate, tryptophan, Cysteine, aspartic acid,

Abstract :

In this study, new derivatives of ((2-chloro-5-(trifluoromethyl) phenyl) carbamic acid) phenyl ester, were synthesized using cysteine, tryptophan, aspartic acid and isoleucine amino acids as well as their methyl esters. These compounds were selected from the four main classes of amino acids: (polar without charg), (nonpolar and aromatic), (polar with negative charge) and (nonpolar and aliphatic) respectively. The molecular structures of all products were identified and confirmed using 1HNMR and FT-IR spectroscopic methods. Finally, pure compounds ((2-chloro-5-(triflouromethyl) phenyl) carbamoyle)-D-tryptophan and 1-(2-chloro-5-(triflouromethyl) phenyl) - 2,6-dioxohexahydropyrimidine-4-carboxylic acid, were tested for their effects on the pheochromocytoma cells’ morphology using microscopic imaging. The calculated lethal dose was 10 mM and the assay time was 48 h. Visual inspection of invert microscope images revealed acceptable lethal effect of synthetic products.

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