Abstract
A series of 5-phenyl-3-(10H-phenothiazinyl)-Δ2-cyclohexen-1-ones were prepared using conventional and microwave-assisted methods. The condensation between 3-phenyl-1-(10H-phenothiazinyl) prop-2-en-1-one derivatives (3a–g) and acetyl acetone yielded 5-phenyl-3-(10H-phenothiazinyl)-Δ2-cyclohexen-1-one derivatives (7a–g). The products were characterized by UV, IR, 1H NMR, 13C NMR, 2D-NMR, MS, and elemental analysis. In vitro antifungal activity was carried out by zone of inhibition method against four species, namely Aspergillus niger, Candida albicans, Microsporum gypseum, and Aspergillus flavus. Compounds 7a and 7d showed good antifungal activity with zones of inhibition of 17 and 18 mm, respectively, and comparable with the standard substance, Bavinston, with 20 mm.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
S. Bansod, M. Rai, World J. Med. Sci. 3(2), 81 (2008)
S.K. Srivastava, S.L. Srivastava, S.D. Srivastava, J. Indian Chem. Soc. 77, 104 (2000)
A. Singh, P.S. Naidu, P.M. Mahajanab, S.K. Kulkarni, J. Pharm. Sci. 8, 182 (2005)
W.H. Timberlake, R.S. Sehwab, New Eng. J. Med. 247, 98 (1952)
J.J. Gorden, Nature 162, 144 (1948)
D. Lednicer, L. A. Mitscher, The organic chemistry of drug synthesis (Wiley, New York, 1976), vol. 1
H.O. House, Modern synthetic reactions, 2nd edn. (Benjamin, New York, 1972)
E.D. Bergman, D. Ginsburg, R. Pappo, Org. React. 10, 179 (1959)
A. Garcia-Raso, J. Garcia-Raso, B. Campaner, R. Mestres, J.V. Sinisterra, Synthesis 12, 1037 (1982)
J.L. Soto, C. Seoane, A.M. Mansilla, M. Quinterio, Org. Prep. Proced. Int. 14, 319 (1982)
K.I. Watanabe, K.I. Miyazu, K. Irie, Bull. Chem. Soc. Jpn. 55, 3212 (1982)
B.M. Choudry, M. Lakshmi Kantam, B. Kavita, C. Venkat Reddy, F. Figueras, Tetrahedron 56, 9357 (2000)
K. Shibata, I. Katsuyama, M. Matsui, H. Muramatsu, Bull. Chem. Soc. Jpn. 63, 3710 (1990)
M. Mirza-Agayan, G. Etemad-Moghadam, A. Zaparucha, J. Berlan, A. Loupy, M. Koenig, Tetreahedron 6, 2643 (1995)
N. Ratoarinoro, A.M. Wilhelm, J. Berlan, H. Demas, Chem. Eng. J. 50, 27 (1992)
A.N. Mayekar, Int. J. Chem. 2, 114 (2010)
S.N. Sawney, G.S. Dhindsa, V. Dharam, J. Indian Chem. Soc. LXV, 643 (1988)
J. Patocka, A. Dvorak, J. Appl. Biomed. 2, 95 (2004)
M. Gopalakrishnan, J. Thanusu, V. Kanakarajan, R. Govindaraju, Med. Chem. Res. 18, 341 (2009)
R.K. Upadhyay, M.S. Upadhyay, S. Jain, E J. Chem. 6, 254 (2009)
A.V. Saranya, R. Subban, Res. J. Recent Sci. 1(12), 40 (2012)
A.V. Saranya, R. Subban, S. Venkatachalapathi, Res. J. Chem. Sci. 3(1), 82 (2013)
X. Tang, F. Xue, H. Ma, X. Cao, C. Chen, X. Li, Res. Chem. Intermed. (2012). doi:10.1007/s11164-012-0596-8
Acknowledgments
We are grateful to the Management, Karpagam University, Coimbatore, Tamil Nadu, India, for providing the facilities to carry out the research work. And I am also grateful to my beloved parents (Father: A.D. Velusamy; Mother: V. Selvam) for their encouragement.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Saranya, A.V., Ravi, S. Synthesis of 5-phenyl-3-(10H-phenothiazinyl)-Δ2-cyclohexen-1-ones by conventional and microwave-assisted methods and their antifungal activity. Res Chem Intermed 40, 3085–3093 (2014). https://doi.org/10.1007/s11164-013-1153-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-013-1153-9