BIOLOGICAL ACTIVITY STUDIES OF SOME SYNTHESIZED NOVEL FURAN AND PYRAN DERIVATIVES

Abstract

In this study, some novel furan and pyran derivatives 1-[4-(1-hydroxyethyl)-2-methyl-5-phenyl-4,5 dihydrofuran-3-il]ethanone (1);  1-(4-Hydroxymethyl-5,5-dimethyl-2-phenyl-4,5-dihydro-furan-3-il)ethanone (2);  Ethyl 2-methyl-5-phenyl-5-styryl-4,5-dihydro-furan-3-carboxylate (3);  Ethyl 4-hydroxymethyl-2,5,5-trimethyl-4,5-dihydro-furan-3-carboxylate (4);  Ethyl 4-(1-hydroxy-ethyl)-2-methyl-5-phenyl-4,5-dihydro-furan-3-carboxylate (5) Ethyl 5-hydroxy-2,6,6-trimethyl-5,6-dihydro-4H-pyran-3-carboxylate (6) were synthesized as mentioned in our previous report [1].

The in vitro novel furan and pyran derivatives were investigated for antibacterial activity against gram-positive bacteria i.e. Bacillus licheniformis M30 , Bacillus megaterium M22, Bacillus circulans M34, Bacillus subtilis B1 , Bacillus subtilis M33 , Bacillus cereus B9,  Staphylococcus aureus ATCC 653,  Micrococcus luteus M3 and gram-negative i.e. Escherichia coli ATCC 25922 , and as a fungus  Pseudomonas aeruginosa P7. The antibacterial  and antifungal activities were determined by the disc diffusion method (DISC) and minimum inhibition concentration (MIC) against the tested gram-positive and gram-negative bacteria and fungus. The inhibition zones were compared with those of reference discs which were studied in our previous work [2]. Reference discs used for control were as follows ketoconazole, ampicillin, tetracycline, penicillin, chloramphenicol, and gentamicin. From the results it could be said that some of the chemical compound can be used as a raw medicine sources.  Their antibiogram tests showed better results than some known antibiotics.

Keywords

• Antibacterial Activity,Antifungal Activity,Furan,Pyran

References

1. H. Aslan, D. E. Akpınar, A. Öktemer, M. Yakut, and O. Alagöz, "Synthesis of Dihydropyrans and Dihydrofurans via Radical Cyclization of Unsaturated Alcohols and 1, 3‐Dicarbonyl Compounds," Helvetica Chimica Acta, vol. 97, pp. 652-663, 2014.
2. E. Loğoğlu, M. Yilmaz, H. Katircioğlu, M. Yakut, and S. Mercan, "Synthesis and biological activity studies of furan derivatives," Medicinal chemistry research, vol. 19, pp. 490-497, 2010.
3. R. V. Chambhare, B. G. Khadse, A. S. Bobde, and R. H. Bahekar, "Synthesis and preliminary evaluation of some N-[5-(2-furanyl)-2-methyl-4-oxo-4H-thieno [2, 3-d] pyrimidin-3-yl]-carboxamide and 3-substituted-5-(2-furanyl)-2-methyl-3H-thieno [2, 3-d] pyrimidin-4-ones as antimicrobial agents," European journal of medicinal chemistry, vol. 38, pp. 89-100, 2003.
4. C. Kirilmis, M. Ahmedzade, S. Servi, M. Koca, A. Kizirgil, and C. Kazaz, "Synthesis and antimicrobial activity of some novel derivatives of benzofuran: Part 2. The synthesis and antimicrobial activity of some novel 1-(1-benzofuran-2-yl)-2-mesitylethanone derivatives," European Journal of Medicinal Chemistry, vol. 43, pp. 300-308, 2008.
5. C. J. Douglas, H. M. Sklenicka, H. C. Shen, D. S. Mathias, S. J. Degen, G. M. Golding, et al., "Synthesis and UV studies of a small library of 6-aryl-4-hydroxy-2-pyrones. A relevant structural feature for the inhibitory property of arisugacin against acetylcholinesterase," Tetrahedron, vol. 55, pp. 13683-13696, 1999.
6. A. Evidente, A. Cabras, L. Maddau, S. Serra, A. Andolfi, and A. Motta, "Viridepyronone, a new antifungal 6-substituted 2 h-pyran-2-one produced by Trichoderma viride," Journal of agricultural and food chemistry, vol. 51, pp. 6957-6960, 2003.
7. Z. Liu and J. Meinwald, "5-(Trimethylstannyl)-2 H-pyran-2-one and 3-(Trimethylstannyl)-2 H-pyran-2-one: New 2 H-Pyran-2-one Synthons," The Journal of organic chemistry, vol. 61, pp. 6693-6699, 1996.
8. M. D. Aytemir, U. Calis, and M. Ozalp, "Synthesis and evaluation of anticonvulsant and antimicrobial activities of 3-hydroxy-6-methyl-2-substituted 4h-pyran-4-one derivatives," Arch Pharm (Weinheim), vol. 337, pp. 281-8, May 2004.

9. I. J. Fairlamb, L. R. Marrison, J. M. Dickinson, F.-J. Lu, and J. P. Schmidt, "2-Pyrones possessing antimicrobial and cytotoxic activities," Bioorganic & medicinal chemistry, vol. 12, pp. 4285-4299, 2004.
10. F. Bellina, M. Biagetti, A. Carpita, and R. Rossi, "Selective synthesis of natural and unnatural 5, 6-disubstituted 2 (2H)-pyranones via iodolactonization of 5-substituted (Z)-2-en-4-ynoic acids," Tetrahedron, vol. 57, pp. 2857-2870, 2001.
11. M. Allen, "A curious brew," Chemistry in Britain, vol. 32, pp. 35-37, 1996.
12. M. Kondoh, T. Usui, S. Kobayashi, K. Tsuchiya, K. Nishikawa, T. Nishikiori, et al., "Cell cycle arrest and antitumor activity of pironetin and its derivatives," Cancer letters, vol. 126, pp. 29-32, 1998.
13. S. Kobayashi, K. Tsuchiya, T. Kurokawa, T. Nakagawa, N. Shimada, and Y. Iitaka, "Pironetin, a novel plant growth regulator produced by Streptomyces sp. NK10958," The Journal of antibiotics, vol. 47, pp. 703-707, 1994.
14. K. Tsuchiya, S. Kobayashi, T. Nishikiori, T. Nakagawa, and K. Tatsuta, "NK10958P, a Novel Plant Growth Regulator Produced by Strcptomyces sp," The Journal of antibiotics, vol. 50, pp. 259-260, 1997.
15. R. V. Shingalapur, K. M. Hosamani, and R. S. Keri, "Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles," European journal of medicinal chemistry, vol. 44, pp. 4244-4248, 2009.
16. H. Katırcıoğlu, E. Loğoğlu, T. Tilki, and A. Öktemer, "Synthesis of 2, 4-dihalogenofluorobenzenes and their antimicrobial and antifungal activity studies," Medicinal Chemistry Research, vol. 16, pp. 205-212, 2007.
17. J. M. Andrews, "Determination of minimum inhibitory concentrations," Journal of antimicrobial Chemotherapy, vol. 48, pp. 5-16, 2001.
18. P. Wayne, "NCCLS (National Committee for Clinical Laboratory Standards) Method for dilution antimicrobial susceptibility tests of bacteria that grow aerobically," Approved Standard. M100-S12, 2002.
19. H. Dorman and S. Deans, "Antimicrobial agents from plants: antibacterial activity of plant volatile oils," Journal of applied microbiology, vol. 88, pp. 308-316, 2000.