Abstract
A novel series of various 2-allylbenzo[d]isoxazol-3(2H)-ones were synthesized using benzo[d]isoxazol-3(2H)-one treated with different allyl bromides/chlorides in the presence of water-mediated cesium carbonate as a new catalyst 3(a-h). The structures of the newly synthesized Benzisoxazole-substituted-allyl derivatives were characterized by spectroscopic methods and mass spectrometry. These synthesized compounds were evaluated for their in vitro antioxidant and anticancer activity. Compounds 3b, d, f, h were identified as the best hit against HT-29 Human colon cancer cells. Similarly, compounds like 3b, d, f, h showed significant antioxidant activity compared to the standard drug butylated hydroxy toluene (BHT).
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
W. A. Denny, G. W. Rewcastle and B. Baguley, J. Med. Chem., 33, 814 (1990).
S. Batra, A. K. Roy, A. Patra, A. P. Bhaduri, W. R. Surin, S. A. V. Raghavan, P. Sharma, K. Kapoor and M. Dikshit, Biorg. Med. Chem., 12, 2059 (2004).
H. Agirbas, S. Guner, F. Budak, S. Keceli, F. Kandemirli, N. Shvets, V. Kovalishyn and A. Dimoglo, Biorg. Med. Chem., 15, 2322 (2007).
M. Pinho and M. V. D. Teresa, Current Org Chem., 9, 925 (2005).
J. F. Swinbourne, H. J. Hunt and G. Klinkert, Adv. Heterocycl. Chem., 3, 103 (1987).
D.D. Stiff and M.A. Zemaitis, Drug Metab Dispos., 18, 888 (1990).
N. J. Hrib, J.G. Jurcak, K. L. Burgher, P.G. Conway, H. B. Hartman, L. L. Kerman, J. E. Roehr and A. T. Woods, J. Med. Chem., 37, 2308 (1994).
M. Jain and C. H. Kwon, J. Med. Chem., 46, 5428 (2003).
M. D. Scobie, J. Org. Chem., 59, 7008 (1994).
H. D. Kendall, J. Med. Chem., 59, 7008 (1994).
A. Nuhrich, M. Varache-Lembege, J. Vercauteren, R. Dokhan, P. Renard and G. Devaux, Eur. J. Med. Chem., 31, 957 (1996).
A. Villalobos, J. F. Blake, C. K. Biggers, T.W. Butler, D. S. Chapin, Y. L. Chen, J. L. Ives, S. B Jones and D. R. Liston, J. Med. Chem., 37, 2721 (1994).
J. Rajeev, D.D. Agarwal and Damodharan, J. Indian Chem. Soc., 72, 825 (1995).
J. C. Saunder and W. R. N. Williamson, J. Med. Chem., 2, 1554 (1979).
J. T. Strupczewski, R. C. Allen, B. A. Gardener, B. L. Schmid, U. Stache, E. J. Glamkowski, M.C. Jones, D. B. Ellis, F. P. Huger and R.W. Dunn, J. Med. Chem., 28, 761 (1985).
P. B. Khedekar, R. H. Bahekar, R. S. Chopade, S. N. Umathe, A. R. Rao and K. P. Bhusari, Drug Res., 53, 640 (2003).
S. K. Agrawal, A. K. Saxena, P. C. Jain, R. N. Sur, R. C. Srimal, B. N. Dhwan and N. Anand, Ind. J. Chem., 26B, 642 (1984).
D. J. C. Constable, P. J. Dunn, J.D. Hayler, G.R. Humphrey, J. L. Leazer Jr., R. J. Linderman, K. Lorenz, J. Manley, B.A. Pearlman, Wells, A. Zaks and T.Y. Zhang, Green Chem., 9, 411 (2007).
Horst boshagen, Chem. Ber, 100, 954 (1967).
J. Carnichael, W.G. DeGraff, A. F. Gazdar, J. D. Minna and J. B. Mitchell, Cancer Res., 47, 936 (1987).
T. Mosmann, J. Immunol. Meth., 65, 55 (1983).
Gulcin, Life Sci., 78, 803 (2007).
Author information
Authors and Affiliations
Corresponding author
Additional information
To whom correspondence should be addressed.
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Anand, M., Selvaraj, V. & Alagar, M. Synthesis, characterization and evaluation of antioxidant and anticancer activities of novel benzisoxazole-substituted-allyl derivatives. Korean J. Chem. Eng. 31, 659–663 (2014). https://doi.org/10.1007/s11814-013-0252-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11814-013-0252-z