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Vol. 26 No. 15 (2014): Vol 26 Issue 15

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Synthesis of 2-Aryl-4H-3,1-Benzoxazin-4-ones: A Class of α-Chymotrypsin Inhibitors

https://doi.org/10.14233/ajchem.2014.16108
Zulfiqar Ali Khan
Department of Chemistry, Government College University, Faisalabad-38000, Pakistan
Noshaba Afzal
Department of Chemistry, Government College University, Faisalabad-38000, Pakistan
Zaib Hussain
Institute of Chemistry, University of the Punjab, Lahore-54000, Pakistan
Syed Ali Raza Naqvi
Department of Chemistry, Government College University, Faisalabad-38000, Pakistan
Ayesha Bari
Department of Chemistry, Government College University, Faisalabad-38000, Pakistan
Sohail Anjum Shahzad
Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad-22060, Pakistan
Muhammad Yar
Interdisciplinary Research Center in Biomedical Materials, COMSATS Institute of Information Technology, Lahore-54000, Pakistan
Nasir Mahmood
Department of Allied Health Sciences and Chemical Pathology, University of Health Sciences, Lahore-54000, Pakistan
Shazia Anwer Bukhari
Department of Chemistry, Government College University, Faisalabad-38000, Pakistan
Asim Mansha
Department of Chemistry, Government College University, Faisalabad-38000, Pakistan
Ameer Fawad Zahoor
Department of Chemistry, Government College University, Faisalabad-38000, Pakistan
Abdur Rahman Khan
Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad-22060, Pakistan
Matloob Ahmad
Department of Chemistry, Government College University, Faisalabad-38000, Pakistan

Corresponding Author(s) : Zulfiqar Ali Khan

zulfiqarchem@gmail.com

Asian Journal of Chemistry, Vol. 26 No. 15 (2014): Vol 26 Issue 15

Abstract

Twenty one derivatives of 2-aryl-4H-3,1-benzoxazin-4-one were synthesized and their potential therapeutically significance and structure-activity relationship were tested against a-chymotrypsin. Majority of synthesized compounds showed significant in vitro a-chymotrypsin inhibitory properties having IC50 values in the range of 5.42 ± 1.66 – 41.27 ± 1.33 μM, whereas standard inhibitor chymostatin have IC50 value 7.13 ± 1.06 μM. In the present series compounds 2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one (3h), 2-(2-bromophenyl)-4H-3,1-benzoxazin-4-one (3n) and 2-(1-naphthyl)-4H-3,1-benzoxazin-4-one (3t) with IC50 values 7.22 ± 0.75, 6.99 ± 0.29 and 5.42 ± 1.66 μM, respectively were found to be most active members of series, even better than standard inhibitor a-chymostatin.

Keywords

2-Aryl-4H-3,1-benzoxazin-4-ones in vitro α-chymotrypsin inhibitory activity Structure-activity relationship
Ali Khan, Z., Afzal, N., Hussain, Z., Ali Raza Naqvi, S., Bari, A., Anjum Shahzad, S., … Ahmad, M. (2014). Synthesis of 2-Aryl-4H-3,1-Benzoxazin-4-ones: A Class of α-Chymotrypsin Inhibitors. Asian Journal of Chemistry, 26(15), 4561–4565. https://doi.org/10.14233/ajchem.2014.16108
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