Synthesis, characterization, solvatochromic properties, and antimicrobial evaluation of 5-acetyl-2-thioxo-dihydro-pyrimidine-4,6-dione-based chalcones

Medicinal Chemistry Research

Volumn 22, Issue 9, 2013, Pages 4075-4086

  Dhorajiya, Bhaveshkumar D ^a   Bhakhar, Bhimji S ^a   Dholakiya, Bharatkumar Z ^a  

^a SARDAR VALLABHBHAI NATIONAL INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Antibacterial activity; Antifungal activity; Chalcones

Indexed keywords

5 (3 NAPHTHALEN 2 YL ACRYLOYL) 2 THIOXO DIHYDRO PYRIMIDINE 4,6 DIONE; 5 (3 PHENYLACRYLOYL) 2 THIOXO DIHYDRO PYRIMIDINE 4, 6 DIONE; 5 [3 (2 CHLOROPHENYL)ACRYLOYL] 2 THIOXO DIHYDRO PYRIMIDINE 4,6 DIONE; 5 [3 (2 HYDROXYPHENYL)ACRYLOYL] 2 THIOXO DIHYDRO PYRIMIDINE 4,6 DIONE; 5 [3 (3 METHOXYPHENYL)ACRYLOYL] 2 THIOXO DIHYDRO PYRIMIDINE 4,6 DIONE; 5 [3 (3 NITROPHENYL)ACRYLOYL] 2 THIOXO DIHYDRO PYRIMIDINE 4,6 DIONE; 5 [3 (3,4 DIMETHOXYPHENYL)ACRYLOYL] 2 THIOXO DIHYDRO PYRIMIDINE 4,6 DIONE; 5 [3 (4 CHLOROPHENYL)ACRYLOYL] 2 THIOXO DIHYDRO PYRIMIDINE 4,6 DIONE; 5 [3 (4 HYDROXYPHENYL)ACRYLOYL] 2 THIOXO DIHYDRO PYRIMIDINE 4,6 DIONE; 5 [3 (4 NITROPHENYL)ACRYLOYL] 2 THIOXO DIHYDRO PYRIMIDINE 4,6 DIONE; ALDEHYDE DERIVATIVE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; CHALCONE DERIVATIVE; GRISEOFULVIN; THIOBARBITURIC ACID DERIVATIVE; THIOXO 5 (3 PARA TOLYL ACRYLOYL)DIHYDRO PYRIMIDINE 4,6 DIONE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS CLAVATUS; BACTERIAL STRAIN; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; ESCHERICHIA COLI; FUNGAL STRAIN; INFRARED SPECTROSCOPY; KLEBSIELLA PNEUMONIAE; MINIMUM BACTERICIDAL CONCENTRATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PENICILLIUM; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PYOGENES; STRUCTURE ACTIVITY RELATION; TRICHOPHYTON RUBRUM; ULTRAVIOLET SPECTROSCOPY;

EID: 84881148538     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0395-1     Document Type: Article

References (23)

1. Alzoreky NS, Nakahara K (2003) Antibacterial activity of extracts from some edible plants commonly consumed in Asia. Int J Food Microbiol 80:223-230
2. Andres P, Marhold A (1996) A new synthesis of 5-trifluoromethyluracil source. J Fluor Chem 77:93-95
3. Anto RJ, Sukumaran K, Kuttana G, Rao MNA, Subbaraju V, Kuttana R (1995) Anticancer and antioxidant activity of synthetic chalcones and related compounds. Cancer Lett 97:33-37
4. Basavaraja HS, Jayadevaiah KV, Mumtaz MH, Vijay Kumar MMJ, Basavaraj P (2010) Synthesis of novel piperazine and morpholine linked substituted pyrimidine derivatives as antimicrobial agents. J Pharm Sci Res 2:5-12
5. Bauer AW, Kirby WM, Sherris JC, Turck M (1966) Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol 45:493-496
6. Branko SJ, Donna MN (2001) Preparation of 5-formyl- and 5-acetylbarbituric acids, including the corresponding Schiff bases and phenylhydrazones. Tetrahedron Lett 42:8435-8439
7. Dhorajiya BD, Malani MH, Patel JR, Dholakiya BZ (2012) Antimicrobial activities of synthesized and characterized 5-acetyl pyrimidine-2,4,6-(1H, 3H, 5H)-trione based chalcone. Der Pharm Chem 4:141-146
8. Fattah OF, Abbas EMH, Mohemed NM, Abd-Elmoez SI (2010) Synthesis and evaluation of some tetrahydropyrimidine derivatives as antimicrobial agents. Aust J Basic Appl Sci 4:27-36
9. Holy A, Votruba I, Masojidkova M, Andrei G, Snoeck R, Naesens L, De Clercq E, Balzarini J (2002) 6-[2-(Phosphonomethoxy)alkoxy]pyrimidines with antiviral activity. J Med Chem 45:1918-1929
10. Hsu YL, Kuo PL, Tzeng WS, Lin CC (2006) Chalcone inhibits the proliferation of human breast cancer cell by blocking cell cycle progression and inducing apoptosis. Food Chem Toxicol 44:704-713
11. Jacobson (1937) US Patent 2,090,594 [C. A. 31, 7068]
12. Kashman Y, Hirsh S, McConnell OJ, Ohtani I, Kusumi T, Kakisawa H (1989) Ptilomycalin A: a novel polycyclic guanidine alkaloid of marine origin. J Am Chem Soc 111:8925-8926
13. Lee SH, Seo GS, Kim JY, Jin XY, Kim HD, Sohn DH (2006) Heme oxygenase 1 mediates anti-inflammatory effects of 2′,4′,6′- tris(methoxymethoxy) chalcone. Eur J Pharmacol 532:178-186
14. Lopez SN, Castelli MV, Zacchino SA, Domínguez JN, Lobo G, Charris-Charris J, Cortes JC, Ribas JC, Devia C, Rodriguez AM, Enriz RD (2001) In vitro antifungal evaluation and structure-activity relationships of a new series of chalcone derivatives and synthetic analogues, with inhibitory properties against polymers of the fungal cell wall. Bioorg Med Chem 9:1999-2013
15. Lui MP, Wilairat SL, Croft LC, Tan A, Go ML (2003) Structure-activity relationships of antileishmanial and antimalarial chalcones. Bioorg Med Chem 11:2729-2738
16. Nace Z, Danijel K (2011) Preparation and reactivity of 5-benzylidenebarbituric and 5-benzylidene-2-thiobarbituric acids. Acta Chim Slov 58:151-157
17. Nowakowska Z (2007) A review of anti-infective and anti-inflammatory chalcones. Eur J Med Chem 42:125-137
18. Reddick JJ, Saha S, Lee J, Melnick JS, Perkins J, Begley TP (2001) The mechanism of action of bacimethrin, a naturally occurring thiamin antimetabolite. Bioorg Med Chem Lett 11:2245-2248
19. Rios JL, Recio MC, Villar A (1988) Screening methods for natural products with antimicrobial activity: a review of the literature. J Ethnopharmacol 23:127-149
20. Siddiqui ZN, Musthafa TN, Ahmad A, Khan AU (2011) Thermal solvent-free synthesis of novel pyrazolyl chalcones and pyrazolines as potential antimicrobial agents. Bioorg Med Chem Lett 15:2860-2865
21. Silverstein RM, Webster FX (1997) Spectrometric identification of organic compounds, 6th edn. Wiley, New York, pp 79-223
22. Tomar V, Bhattacharjee G, Kamaluddina, Kumar A (2007) Synthesis and antimicrobial evaluation of new chalcones containing piperazine or 2,5-dichlorothiophene moiety. Bioorg Med Chem Lett 17:5321-5324
23. Yi X, Zheng-Yu Y, Peng X, Kenneth FB, Yuka N, Kuo-Hsiung L (2000) Antitumor agents. Part 202: novel 2′-amino chalcones: design, synthesis and biological evaluation. Bioorg Med Chem Lett 10:699-701