Synthesis, characterization and evaluation of antioxidant and anticancer activities of novel benzisoxazole-substituted-allyl derivatives

Mohanam Anand; Vaithialingam Selvaraj; Muthukaruppan Alagar

Korean Journal of Chemical Engineering, Vol.31, No.4, 659-663, April, 2014

DOI10.1007/s11814-013-0252-z Export Citation

Synthesis, characterization and evaluation of antioxidant and anticancer activities of novel benzisoxazole-substituted-allyl derivatives

Mohanam Anand, Vaithialingam Selvaraj¹, and Muthukaruppan Alagar^{2, †}

Science and Humanities, Department of Chemistry, Kingston Engineering College, Vellore-59, India
¹Department of Chemistry, University College of Engineering-Villupuram, (A Constituent College of Anna University, Chennai-25), Kakuppam, Villupuram-605103, India
²Department of Chemical Engineering, A. C. Tech Campus, Anna University, Chennai-600025, TN, India

E-mail:

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).

Keywords:2-Allylbenzo[d]isoxazol-3(2H)-ones;Antioxidant Activity;Anticancer Activity

[References]

Denny WA, Rewcastle GW, Baguley B, J. Med. Chem., 33, 814 (1990)
Batra S, Roy AK, Patra A, Bhaduri AP, Surin WR, Raghavan SAV, Sharma P, Kapoor K, Dikshit M, Biorg. Med. Chem., 12, 2059 (2004)
Agirbas H, Guner S, Budak F, Keceli S, Kandemirli F, Shvets N, Kovalishyn V, Dimoglo A, Biorg. Med. Chem., 15, 2322 (2007)
Pinho M, Teresa MVD, Current Org Chem., 9, 925 (2005)
Swinbourne JF, Hunt HJ, Klinkert G, Adv. Heterocycl. Chem., 3, 103 (1987)
Stiff DD, Zemaitis MA, Drug Metab Dispos., 18, 888 (1990)
Hrib NJ, Jurcak JG, Burgher KL, Conway PG, Hartman HB, Kerman LL, Roehr JE, Woods AT, J. Med. Chem., 37, 2308 (1994)
Jain M, Kwon CH, J. Med. Chem., 46, 5428 (2003)
Scobie MD, J. Org. Chem., 59, 7008 (1994)
Kendall HD, J. Med. Chem., 59, 7008 (1994)
Nuhrich A, Varache-Lembege M, Vercauteren J, Dokhan R, Renard P, Devaux G, Eur. J. Med. Chem., 31, 957 (1996)
Villalobos A, Blake JF, Biggers CK, Butler TW, Chapin DS, Chen YL, Ives JL, Jones SB, Liston DR, J. Med. Chem., 37, 2721 (1994)
Rajeev J, Agarwal DD, Damodharan, J. Indian Chem. Soc., 72, 825 (1995)
Saunder JC, Williamson WRN, J. Med. Chem., 2, 1554 (1979)
Strupczewski JT, Allen RC, Gardener BA, Schmid BL, Stache U, Glamkowski EJ, Jones MC, Ellis DB, Huger FP, Dunn RW, J. Med. Chem., 28, 761 (1985)
Khedekar PB, Bahekar RH, Chopade RS, Umathe SN, Rao AR, Bhusari KP, Drug Res., 53, 640 (2003)
Agrawal SK, Saxena AK, Jain PC, Sur RN, Srimal RC, Dhwan BN, Anand N, Ind. J. Chem., 26, 642 (1984)
Constable DJC, Dunn PJ, Hayler JD, Humphrey GR, Leazer JL, Linderman RJ, Lorenz K, Manley J, Pearlman BA, Wells, Zaks A, Zhang TY, Green Chem., 9, 411 (2007)
Horst boshagen, Chem. Ber, 100, 954 (1967)
Carnichael J, DeGraff WG, Gazdar AF, Minna JD, Mitchell JB, Cancer Res., 47, 936 (1987)
Mosmann T, J. Immunol. Meth., 65, 55 (1983)
Gulcin, Life Sci., 78, 803 (2007)

[1] Denny WA, Rewcastle GW, Baguley B, J. Med. Chem., 33, 814 (1990)

[2] Batra S, Roy AK, Patra A, Bhaduri AP, Surin WR, Raghavan SAV, Sharma P, Kapoor K, Dikshit M, Biorg. Med. Chem., 12, 2059 (2004)

[3] Agirbas H, Guner S, Budak F, Keceli S, Kandemirli F, Shvets N, Kovalishyn V, Dimoglo A, Biorg. Med. Chem., 15, 2322 (2007)

[4] Pinho M, Teresa MVD, Current Org Chem., 9, 925 (2005)

[5] Swinbourne JF, Hunt HJ, Klinkert G, Adv. Heterocycl. Chem., 3, 103 (1987)

[6] Stiff DD, Zemaitis MA, Drug Metab Dispos., 18, 888 (1990)

[7] Hrib NJ, Jurcak JG, Burgher KL, Conway PG, Hartman HB, Kerman LL, Roehr JE, Woods AT, J. Med. Chem., 37, 2308 (1994)

[8] Jain M, Kwon CH, J. Med. Chem., 46, 5428 (2003)

[9] Scobie MD, J. Org. Chem., 59, 7008 (1994)

[10] Kendall HD, J. Med. Chem., 59, 7008 (1994)

[11] Nuhrich A, Varache-Lembege M, Vercauteren J, Dokhan R, Renard P, Devaux G, Eur. J. Med. Chem., 31, 957 (1996)

[12] Villalobos A, Blake JF, Biggers CK, Butler TW, Chapin DS, Chen YL, Ives JL, Jones SB, Liston DR, J. Med. Chem., 37, 2721 (1994)

[13] Rajeev J, Agarwal DD, Damodharan, J. Indian Chem. Soc., 72, 825 (1995)

[14] Saunder JC, Williamson WRN, J. Med. Chem., 2, 1554 (1979)

[15] Strupczewski JT, Allen RC, Gardener BA, Schmid BL, Stache U, Glamkowski EJ, Jones MC, Ellis DB, Huger FP, Dunn RW, J. Med. Chem., 28, 761 (1985)

[16] Khedekar PB, Bahekar RH, Chopade RS, Umathe SN, Rao AR, Bhusari KP, Drug Res., 53, 640 (2003)

[17] Agrawal SK, Saxena AK, Jain PC, Sur RN, Srimal RC, Dhwan BN, Anand N, Ind. J. Chem., 26, 642 (1984)

[18] Constable DJC, Dunn PJ, Hayler JD, Humphrey GR, Leazer JL, Linderman RJ, Lorenz K, Manley J, Pearlman BA, Wells, Zaks A, Zhang TY, Green Chem., 9, 411 (2007)

[19] Horst boshagen, Chem. Ber, 100, 954 (1967)

[20] Carnichael J, DeGraff WG, Gazdar AF, Minna JD, Mitchell JB, Cancer Res., 47, 936 (1987)

[21] Mosmann T, J. Immunol. Meth., 65, 55 (1983)

[22] Gulcin, Life Sci., 78, 803 (2007)