Synthesis, Spectral Characterization and a-Chymotrypsin Activity of 7-O-Substituted Derivatives of 7-Hydroxy-4-methyl-1-benzopyran-2-one

Tehseen Ilyas1; Muhammad Athar Abbasi1; Khadija Nafeesa1; Shaista Khaliq1; Kaniz Rubab1; Ghulam Hussain1; Shazia Khurshid1; Irshad Ahmad2

doi:10.14233/ajchem.2014.15374

Issue

Vol. 26 No. 2 (2014): Vol 26 Issue 2

Issue Published : January 15, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Spectral Characterization and a-Chymotrypsin Activity of 7-O-Substituted Derivatives of 7-Hydroxy-4-methyl-1-benzopyran-2-one

https://doi.org/10.14233/ajchem.2014.15374

Tehseen Ilyas1

1Department of Chemistry, Government College University, Lahore-54000, Pakistan 2Department of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur-63100, Pakistan *Corresponding author: Tel: +92 42 111000010, Ext. 450; E-mail: azizryk@yahoo.com

Muhammad Athar Abbasi1

Khadija Nafeesa1

Shaista Khaliq1

Kaniz Rubab1

Ghulam Hussain1

Shazia Khurshid1

Irshad Ahmad2

Asian Journal of Chemistry, Vol. 26 No. 2 (2014): Vol 26 Issue 2
Article Published : January 16, 2014

Abstract

In this work, a series of O-alkyl/arenyl/acyl substituted derivatives of 7-hydorxy-4-methyl-1-benzenpyran-2-one (3a-l) was synthesized. The parent compound 7-hydroxy-4-methyl-1-benzenpyran-2-one (1) was geared up by the coupling of resorcinol (a) with ethylacetoacetate (b) in the presence of conc. sulphuric acid. Further, O-substituted derivatives of parent compound were prepared by treating with different electrophiles (2a-l) using sodium hydride as base and DMF as a solvent. The structure of these synthesized compounds were characterized by IR, EI-MS and ¹H NMR. These derivatives were also screened against a-chymotrypsin enzyme to check their enzyme inhibition activity. All the compounds displayed a-chymotrypsin activity to varying degree.

Keywords

7-Hydroxy-4-methyl-1-benzopyran-2-one a-Chymotrypsin enzyme 1H NMR EI-MS.

Ilyas1, T., Athar Abbasi1, M., Nafeesa1, K., Khaliq1, S., Rubab1, K., Hussain1, G., … Ahmad2, I. (2014). Synthesis, Spectral Characterization and a-Chymotrypsin Activity of 7-O-Substituted Derivatives of 7-Hydroxy-4-methyl-1-benzopyran-2-one. Asian Journal of Chemistry, 26(2), 326–330. https://doi.org/10.14233/ajchem.2014.15374

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References

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References

A.A. Al-Rifai, M.T. Ayoub, A.K. Shakya, K.A. Abu Safieh and M.S. Mubarak, Med. Chem. Res., 21, 468 (2012); doi:10.1007/s00044-011-9553-0.

F. Maggi, L. Barboni, G. Caprioli, F. Papa, M. Ricciutelli, G. Sagratini and S. Vittori, Fitoterapia, 82, 1215 (2011); doi:10.1016/j.fitote.2011.08.011.

M. Raters and R. Matissek, Eur. Food Res. Technol., 227, 637 (2008); doi:10.1007/s00217-007-0767-9.

S.L. Born, A.M. Api, R.A. Ford, F.R. Lefever and D.R. Hawkins, Food Chem. Toxicol., 41, 247 (2003); doi:10.1016/S0278-6915(02)00227-2.

D.M. Anderson, S. Shelley, N. Crick and M. Buraglio, J. Clin. Pharmacol., 42, 1358 (2002); doi:10.1177/0091270002238772.

M.A. Gouda, M.A. Berghot, E.A. Baz and W.S. Hamama, Med. Chem. Res., 21, 1062 (2012); doi:10.1007/s00044-011-9610-8.

N.N. Farshori, M.R. Banday, A. Ahmad, A.U. Khan and A. Rauf, Med. Chem. Res., 20, 535 (2011); doi:10.1007/s00044-010-9347-9.

N. Ingale, V. Maddi, M. Palkar, P. Ronad, S. Mamledesai, A.H.M. Vishwanathswamy and D. Satyanarayana, Med. Chem. Res., 21, 16 (2012); doi:10.1007/s00044-010-9494-z.

N. Gacche and S.G. Jadhav, J. Exp. Clin. Med., 4, 165 (2012); doi:10.1016/j.jecm.2012.04.007.

Y. Shi and C.H. Zhou, Bioorg. Med. Chem. Lett., 21, 956 (2011); doi:10.1016/j.bmcl.2010.12.059.

I.M. Berquin and B.F. Sloane, Adv. Exp. Med. Biol., 389, 281 (1996); doi:10.1007/978-1-4613-0335-0_35.

J.L. Imler and J.A. Hoffmann, Curr. Opin. Microbiol., 3, 16 (2000); doi:10.1016/S1369-5274(99)00045-4.

S. Iwanaga, Curr. Opin. Immunol., 5, 74 (1993); doi:10.1016/0952-7915(93)90084-6.

R.J.P. Cannell, S.J. Kellam, A.M. Owsianka and J.M. Walker, Planta Med., 54, 10 (1988); doi:10.1055/s-2006-962319.

Issue

Vol. 26 No. 2 (2014): Vol 26 Issue 2

Synthesis, Spectral Characterization and a-Chymotrypsin Activity of 7-O-Substituted Derivatives of 7-Hydroxy-4-methyl-1-benzopyran-2-one

Abstract

Keywords

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