Startseite Lebenswissenschaften Synthesis and biological evaluation of novel pyrimidines derived from 6-aryl-5-cyano-2-thiouracil
Artikel
Lizenziert
Nicht lizenziert Erfordert eine Authentifizierung

Synthesis and biological evaluation of novel pyrimidines derived from 6-aryl-5-cyano-2-thiouracil

  • Asma Mohamed Mahran EMAIL logo , Nasser Abdelhamid Hassan , Dalia Ahmed A. Osman , Sherif Shaban Ragab und Allam Abdelhamid Hassan
Veröffentlicht/Copyright: 21. April 2016

Abstract

Starting from 6-aryl-5-cyano-2-thiouracil derivative 1a–f, a series of novel thiazolo[3,2-a]pyrimidines 4a–f were synthesized. The mechanism and the regioselectivity of the studied reactions are discussed. In addition, a series of tetrahydro-4-H-pyrimido[2,1-b][1,3]thiazines 7a–e and 2-((ethoxymethyl)thio)-4-aryl-1,6-dihydropyrimidines 9b,c,e were synthesized. The anti-microbial activities of some of the prepared compounds were screened, and the results revealed that compounds 3c and 4c were more active than the standard (Ampicillin) against gram positive bacteria (Pseudomonas aeruginosa). Moreover, compounds 4b,e and 3f were found to be good antifungal agents against the studied fungal strains.

References

1. Lee HW, Kim BY, Ahn JB, Kang SK, Lee JH, Shin JS, et al. Molecular design, synthesis, and hypoglycemic and hypolipidemic activities of novel pyrimidine derivatives having thiazolidinedione. Eur J Med Chem 2005;40:862–74.10.1016/j.ejmech.2005.03.019Suche in Google Scholar

2. Buddh MB, Bapodra AH, Ladva KD. Synthesis and biological evaluation of thiazolo [3,2-α] pyrimidine derivatives as a new type of potential antinmicrobial agents. Ras J Chem 2011;4:824–8.Suche in Google Scholar

3. Bahashwan SA, Fayed AA, Ramadan MA, Amr AE, Al-Harbi NO. Next Steps in Advancing Publication. Arch Pharm Chem Life Sci 2015; 348:1–12.10.1002/ardp.201570004Suche in Google Scholar

4. Nagrajaiah H, Mkhazil I, Begum NS. Synthesis, characterization and biological evaluation of thiazolopyrimidine derivatives. J Chem Sci 2012;124:847–55.10.1007/s12039-012-0271-zSuche in Google Scholar

5. Ram SG, Rajesh PG and Parhate VV. Synthesis, characterization and antibacterial activities of some new Bromo/Nitro 1,3-thiazines. Rasayan J Chem 2013;6:65–7.Suche in Google Scholar

6. Varalakshmi DP, Ramesh GP, Keerthi K, Ramkrishna G. Synthesis and biological evaluation of different thiazine derivatives. J of Pharmacy Res 2011;4:274–5.Suche in Google Scholar

7. Bozsing D, Sohar P, Gigler G, Kovacs G. Synthesis and pharmacological study of new 3,4-dihydro-2H,6H-pyrimido-[2,1-b][1,3]thiazines. Eur J Med Chem 1996;31:663–8.10.1016/0223-5234(96)85874-0Suche in Google Scholar

8. Ding Y, Girardet J, Smith KL, Larson G, Prigaro B, Wu J, et al. Parallel synthesis of 5-cyano-6-aryl-2-thiouracil derivatives as inhibitors for hepatitis C viral NS5B RNA-dependent RNA polymerase. Bioorganic Chem 2006;34:26–38.10.1016/j.bioorg.2005.10.001Suche in Google Scholar PubMed

9. Berenguer M, Wright TL. Hepatitis B and C viruses: molecular identification and targeted antiviral therapies. Proc Assoc Am Physicians 1998;110:98–112.Suche in Google Scholar

10. Mahran AM, Farghaly TA, Nada AA. Hydrazonoyl halides in heterocycles: synthesis and anti-microbial activity of new 1,2,4-benzotriazine and bis-1,2,4-benzotriazine derivatives. Res Chem Intermed 2015;41:2961–9.10.1007/s11164-013-1404-9Suche in Google Scholar

11. Mahran AM, Ragab SS, Hashem AI, Ali MM, Nada AA. Synthesis and antiproliferative activity of novel polynuclear heterocyclic compounds derived from 2,3-diaminophenazine. Eur J Med Chem 2015;90:568–78.10.1016/j.ejmech.2013.12.007Suche in Google Scholar PubMed

12. Mahran AM, Hassan NA. A one-step synthesis and antimicrobial activities of new substituted dihydro-1,3,4-thiadiazoles. Arch Pharm Res 2006;29:46–9.10.1007/BF02977467Suche in Google Scholar PubMed

13. Shawali AS, Mahran AM, Nada AA. Synthesis and antimicrobial activity of new functionalized derivatives of [1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-one. J Heteroatom Chem 2007;18:393–8.10.1002/hc.20311Suche in Google Scholar

14. Bauer AW, Kirby WM, Sherris JC, Turck M. Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol 1966;45:493–6.10.1093/ajcp/45.4_ts.493Suche in Google Scholar

15. Pfaller MA, Burmeister L, Bartlett MS, Rinaldi MG. Multicenter evaluation of four methods of yeast inoculum preparation. J Clin Microbiol 1988;26:1437–41.10.1128/jcm.26.8.1437-1441.1988Suche in Google Scholar

16. Villanova PA. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically–third edition: Approved Standard. NCCLS, M7-A3.ACCS, 1993.Suche in Google Scholar

17. Villanova PA. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. NCCLS, M7-A3.ACCS, 1997.Suche in Google Scholar

18. Wayne PA. Reference method for broth dilution antifungal susceptibility testing of conidialforming filamentous fungi. Approved standard NCCLS M38-A. NCCLS 2002.Suche in Google Scholar

19. Wayne, PA. Method for antifungal disk diffusion susceptibility testing of yeasts: proposed guideline M44-P. NCCLS, 2003.Suche in Google Scholar

20. Liebowitz LD, Ashbee HR, Evans EG, Chong Y, Mallatova N, Zaidi M, et al. A two year global evaluation of the susceptibility of Candida species to fluconazole by disk diffusion. Global Diagn Microbial Infect Dis 2001;4:27–33.10.1016/S0732-8893(01)00243-7Suche in Google Scholar

21. Matar MJ, Ostrosky-Zeichner L, Paetznick VL, Rodringuez JR, Chen E, Rex JH. Correlation between e-test, disk diffusion, and microdilution methods for antifungal susceptibility testing of fluconazole and voriconazole. Antimicrobial Agents Chemother 2003;47:1647–51.10.1128/AAC.47.5.1647-1651.2003Suche in Google Scholar

22. Ram VJ, Vanden Berghe DA, Vlietinck AJ. 5-Cyano-6-aryluracil and 2-thiouracil derivatives as potential chemotherapeutic agents. IV. J Het Chem 1984;21:1307–12.10.1002/jhet.5570210513Suche in Google Scholar

23. Abdo IM, Strekowski L. A facile synthesis of 6-Aryl-5-cyano-1-(β-d-pyranosyl or β-d-furanosyl)-2-thiocytosines. Tetrahedron 2000;56:8631–6.10.1016/S0040-4020(00)00807-3Suche in Google Scholar

24. Ram VJ. Chemotherapeutic agents, XVIII: synthesis of π-deficient pyrimidines and fused pyrimidines as leishmanicidal agents. Arch Pharm (Weinheim Ger) 1990;223:895–9.10.1002/ardp.19903231103Suche in Google Scholar PubMed

25. Ram VJ. Indian J Chem 1989;28B:159–62.Suche in Google Scholar

26. Sodereviciute V, Vainilavicius P. Chemija 1993;2:70.Suche in Google Scholar

27. Shawali AS, Abbas IM, Mahran AM. Facile entries for regioselective synthesis of [1,2,4]triazolo-[4,3-a]pyrimidin-5(1H)-ones from 2-thiouracil. J Iranian Chem Soc 2004;1:33–9.10.1007/BF03245768Suche in Google Scholar

28. AbdelFattah AM, Negm AM, Gaafar AM. Reactions with 6-methyl-2-thiouracil synthesis of dipyrimidino[2,1-b:1′,2′-c]thiazine. A new ring system. Phosphorus Sulfur and Silicon 1992;72:145–156.10.1080/10426509208031548Suche in Google Scholar

Received: 2015-11-27
Revised: 2016-3-10
Accepted: 2016-3-16
Published Online: 2016-4-21
Published in Print: 2016-5-1

©2016 by De Gruyter

Heruntergeladen am 30.12.2025 von https://www.degruyterbrill.com/document/doi/10.1515/znc-2015-0265/html
Button zum nach oben scrollen