Taking into account the high efficacy of 2-arylpropionic acid derivatives among NSAIDs and based on their SARs, we have evaluated the anti-inflammatory, antinociceptive, and antiaggregant activity and ulcerogenic properties of a new synthesized non-protein amino acid (NPAA) derivative S(-)-2-amino-2-methyl-3-phenylpropanoic acid (NPAA-36). A new method of NPAA-36 synthesis was developed and experiments were carried out, which showed that this compound injected in a dose of 10 mg/kg (i.p.) inhibited xylene-induced ear oedema by about 31.1%, which proved its anti-inflammatory properties. The antinociceptive activity of NPAA-36 was assessed in tail-flick test by the ability to increase the tail cut-off latency by 36.78% within 60 min after injection at the same dose. Investigation of the ulcerogenic properties of NPAA-36 demonstrated that it exhibited lower gastrointestinal toxicity than a well-known arylpropionic acid derivative NSAID. Results of in vitro experiments showed the antiplatelet activity registered not in all (only in 41.2%) cases, which might imply lower bleeding. The obtained data indicate that the new NPAAderivative can be a potential basis for the development of new anti-inflammatory drugs with weak side effects.
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References
A. G. Zhamharyan, M. G. Balasanyan, L. G. Zhamharyan, et al., Materials of the 3rd International Conference on Medical Chemistry and CADD, 4(12), 32 – 33 (2014).
A. S. Saghyan and P. Langer, Asymmetric Synthesis of Non-Proteinogenic Amino Acids, Wiley-VCH Verlag GmbH & Co.: KGaA, USA (2016), Ch.1, pp. 1 – 23.
A. S. Saghyan and P. Langer, Asymmetric Synthesis of on-Proteinogenic Amino Acids, Wiley-VCH Verlag GmbH & Co.: KGaA, USA (2016), Ch.9, pp. 376.
C. J. Friel and M. C. Lu, Wilson and Gisvold’s Textbook of Organic Medicinal and Pharmaceutical Chemistry, Lippincott Williams & Wilkins: Philadelphia (2011), Ch. 24, pp. 792 – 806.
C. Sostres, C. J. Gargallo, and M. T. Arroyo, Arthritis Res. Ther., 15(3), 1 – 8 (2013).
F. E. D’Amour and D. L. Smith, JPET, 72(1), 74 – 79 (1941).
G. M. Nazeruddin, H. A. Osman, Y. I. Shaikh, et al., Der Pharm. Lettre, 6(6), 135 – 141 (2014).
H. Dhall, P. Sikka, A. Kumar, et al.,Orient. J. Chem., 32(4), 1831 – 1838 (2016).
H. O. Gulcan, S. Unlu, A. Dimoglo, et al., Arch. Pharm. Chem. Life Sci., No. 348, 55–61 (2015).
M. Petricevic, S. Konosic, B. Biocina, et al., Anaesthesia, No. 71, 636–647 (2016).
R. Borne, M. Levi, and N. Wilson, Foye’s Principles of Medicinal Chemistry, Lippincott Williams & Wilkins: Philadelphia (2013), Ch. 31, pp. 987 – 1044.
S. Tous, M. Fathy, G. Fetih, et al., Int. J. Pharm. Tech. Res., 6(3), 1100 – 1112 (2014).
X. Shang, J. Wang, M. Li, et al., Fitoterapia, No. 82, 716 – 721 (2011.
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Grigoryan, S.H., Zhamharyan, A.G., Saghyan, A.S. et al. Synthesis and Pharmacological Activity of S(-)-2-Amino-2-Methyl-3-Phenylpropanoic Acid. Pharm Chem J 53, 620–623 (2019). https://doi.org/10.1007/s11094-019-02049-1
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DOI: https://doi.org/10.1007/s11094-019-02049-1