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
(استادیار شیمی آلی، دانشکده علوم پایه، واحد تهران مرکزی، دانشگاه آزاد اسلامی، تهران، ایران)
gholamhossein riazi
2
(استاد بیوشیمی، مرکز تحقیقات بیوشیمی و بیوفیزیک، دانشگاه تهران، تهران، ایران)
safiyeh sadat gholestaneh far
3
(کارشناسی ارشد شیمی آلی، دانشکده علوم پایه، واحد تهران مرکزی، دانشگاه آزاد اسلامی، تهران، ایران)
fatemeh sadat hosseini rostami
4
(کارشناسی ارشد شیمی آلی، دانشکده علوم پایه، واحد تهران مرکزی، دانشگاه آزاد اسلامی، تهران، ایران)
hamid mohammad hosseini
5
(کارشناسی ارشد شیمی آلی، دانشکده علوم پایه، واحد تهران مرکزی، دانشگاه آزاد اسلامی، تهران، ایران)
samaneh gholestani
6
(M.Sc. of Organic Chemistry, Dempartment of Chemistry, Centeral Tehran Branch, Islamic Azad University, Tehran, Iran.)
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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_||_[1] Kocovsky, P.; Tetrahedron Letters 27, 5521-5524, 1986.
[2] Curini, M.; Epifano, F.; Maltese, F.; Rosati, O.; Tetrahedron Letters 43, 4895-4897, 2002.
[3] Della Ca, N.; Gabriele, B.; Ruffolo, G.; Veltri, L.; Adv.Synth. Catal. 353, 133-146, 2011.
[4] METCALF, R.L.; Wld. Hit. Org. 44, 43-78, 1971.
[5] Gotor, M.P.; Tetrahedron 49, 10725-10732, 1993.
[6] Galgani, F.; Bocquene, G.; Ices Technique In Marine Enviromental Sciences 12, 0903-2606, 1998.
[7] Sunil P.; Gupte, Anand, B.; Raghunath, V.; Chem. Commun. 24, 2620-2621, 2001.
[8] De Lorenzo, F.; Staiano, N.; Silengo, L.; cancer research 38, 13-15, 1978.
[9] Perveen, Sh.; Fatima, N.; Mohammed Khan, Kh.; Iqbal Choudhary,M.;, J.Chem.Soc.Pak. 32, 338-343, 2010.
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[12] Faisal, H.; Mustatab, H.; Seonghyeok, W.; Azam, A.; Dongyun, SH.; Arch. Pharm. Res. 23, 33-42, 2015.
[13] Talebi Jahromi, K.; “Pesticides Toxicology”, University of Tehran press, Tehran, 2006.
[14] Wagner, J.A.; Glowacka, D.; Journal of Neuroscience Research 25, 453-462, 1990.
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[19] Hiroki, T.; Syo, K.; Takayoshi, S.; Hidehiko, N.; Kohfuku, K.; Naoki, M.; Bioorganic & Medicinal Chemistry Letters 20, 1948-1952, 2010.
[20] Željka, B.; Maja, C.; Ana-Matea, M.; Jan, B.; Mariya, P.; Jos, V.; Molecules 17, 1124-1137, 2012.
[21] David, P.; Joseph, A.; Stephan, K.; Dominique, L.; Peter, H.; Libutti, S.; Journal of Translational Medicine 38, 1-9, 2007.
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[36] Gray, D.E.; American Institute of Physics Handbook, Third Edition, McGraw Hill, USA, 1972.
