Author:
Drapak Iryna, ,Zimenkovsky Borys,Perekhoda Lina,Yeromina Hanna,Ieromina Zinaida,Paykush Marianna,Logoyda Liliya,Lubenets Vira,Holubieva Tetiana,Yaremkevych Roksolana,Shchur Oleksandr,Seredynska Nataliya, , , , , , , , , , ,
Abstract
New 4-aryl-3-(morpholin-4-yl)-2-arylimino-2,3-dihydrothiazole derivatives 1.1-1.16 were obtained using the Hantzsch reaction by condensation of N-(morpholin-4-yl)-N'-arylthioureas with the corresponding α bromoacetophenones in alcohols. Synthesized hydrobromides 1.1-1.8 were formed as crystalline precipitates during the boiling of the reaction mixture. Bases 1.9-1.16 were obtained by neutralizing the corresponding hydrobromides with NH4OH solution. It has been proposed a possible mechanism of the reaction that is based on the study of the structure of the synthesized compounds. The structures of the synthesized compounds were confirmed by 1H NMR spectroscopy with its special techniques (NOESY and ROESY experiments). It has been shown the formation of the isomer 4-(4'-chlorophenyl)-3-(morpholin-4-yl)-2-(4'-chlorophenylamino)-2.3-dihydrothiazole on the basis of compound 1.14. Pharmacological screening of synthesized derivatives of 4-aryl-2-arylimino-2,3-dihydrothiazole compounds revealed the analgesic effect in the model of visceral pain caused by the introduction of acetic acid to white mice. The anti-inflammatory effect of the synthesized compounds was evaluated in vivo by reducing limb edema in rats with carrageenan-induced inflammation. Thus, the synthesized compounds have analgesic and anti-inflammatory activity.
Publisher
Lviv Polytechnic National University
Subject
General Chemical Engineering,General Chemistry
Reference19 articles.
1. [1] Haddani, F.Z.; Guich, A.; Youssoufi, T.; Boudhar, E.M.; Abouqal, R.; Achemlal, L.; Allali, F.; Bahiri, R.; Bouchti, E.I.; Maghraoui, E.I. et al. Comorbidities in Rheumatoid Arthritis: the RBSMR Study. Int. J. Clin. Rheumatol. 2020, 15(1), 10-14.
2. [2] Luque Ramos, A.; Redeker, I.; Hoffmann, F.; Callhoff, J.; Zink, A.; Albrecht, K. Comorbidities in Patients with Rheumatoid Arthritis and Their Association with Patient-reported Outcomes: Results of Claims Data Linked to Questionnaire Survey. J. Reumatol. 2019, 46(6), 547-571. https://doi.org/10.3899/jrheum.180668
3. [3] Roubille, C.; Fesler, P.; Combe, B. Shifting from a Rheumatologic Point of View toward Patient-centered Care in Rheumatoid Arthritis with an Integrated Management of Comorbidities. J. Reumatol. 2019, 46(6), 545-547. https://doi.org/10.3899/jrheum.181379
4. [4] Vogel, H. G.; Vogel W. H. Drug Discovery and Evaluation. Pharmacological Assays. Second Completely Revised, Updated, and Enlarged Edition; Springer, 2002. https://doi.org/10.1007/978-3-662-03333-3
5. [5] Drapak, I.; Zimenkovsky, B.; Perekhoda, L.; Yeromina, H.; Lipakova, K.; Demchuk, I.; Rakhimovа, M. QSAR-Analysis of 1-[2-(R-Phenylimino)-4-methyl-3-(3-[morpholine-4-yl]propyl)-2,3-dihydro-1,3-thiazol-5-yl]ethane-1-ones Derivatives as Potential Antioxidants. Pharmacia 2019, 66(1), 33-40. https://doi.org/10.3897/pharmacia.66.e35083
Cited by
1 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献