Chemical modification of acetaminophen: PASS assisted in vivo anti-inflammatory activity of chalcones, flavanones and Schiff bases

doi:10.5246/jcps.2017.08.069

Journal of Chinese Pharmaceutical Sciences ›› 2017, Vol. 26 ›› Issue (8): 611-620.DOI: 10.5246/jcps.2017.08.069

• Original articles • Previous Articles

Chemical modification of acetaminophen: PASS assisted in vivo anti-inflammatory activity of chalcones, flavanones and Schiff bases

Syed Misbahul Hasan^1,2, Shah Alam Khan³, Kavita Golani¹, Jaswinder Lamba¹, Aftab Ahmad⁴, Asif Husain^1*

1. Department of Pharmaceutical Chemistry, School of Pharmaceutical Education and Research, Jamia Hamdard (Hamdard University), New Delhi, 110062, India
2. Faculty of Pharmacy, Integral University, Lucknow, UP 226026, India
3. Department of Pharmacy, Oman Medical College, PO Box 620, Postal code-130, Muscat, Sultanate of Oman
4. Health Information Technology Department, Jeddah Community College, King Abdulaziz University, Jeddah, Kingdom of Saudi Arabia

Received:2017-04-28 Revised:2017-06-11 Online:2017-08-31 Published:2017-07-05
Contact: Tel.: +91-9891116086, E-mail: drasifhusain@yahoo.com

Abstract

Abstract:

In the present study, synthetic chalcones, flavanones and Schiff bases were prepared starting from paraceamol, and evaluated their anticipated anti-inflammatory activity. Chalcones were synthesized by reacting 3-acetyl-4-hydroxy acetanilide and aromatic aldehydes in alcoholic potassium hydroxide (KOH) solution under Claisen-Schmidt condensation conditions. The chalcones were cyclized in the presence of piperidine in isoamyl alcohol to obtain flavonone derivatives. Schiff bases were synthesized by condensing 3-acetyl-4-hydroxy anilines with aromatic aldehydes in the presence of HCl. These Schiff bases were further reacted with other aromatic aldehydes in alcoholic KOH solution. PASS cheminformatics software was used to predict the anti-inflammatoryactivity of synthesized compounds.PASS software predicted that chalcone-based Schiff bases6a–d contained structural features that can exhibit anti-inflammatory activity. All the prepared derivatives of acetaminophen exhibited moderate to excellent in vivo anti-inflammatory activity in carrageenan-induced edema in rat paw. All the Schiff bases coupled chalcones showed good anti-inflammatory activity compared with the reference drug, diclofenac. Further evaluation of their therapeutic potential and safety profile is required in the future study.

Key words: p-Acetaminophen, Anti-inflammatory, Chalcone, Flavanone

CLC Number:

R916

Supporting:

Syed Misbahul Hasan, Shah Alam Khan, Kavita Golani, Jaswinder Lamba, Aftab Ahmad, Asif Husain. Chemical modification of acetaminophen: PASS assisted in vivo anti-inflammatory activity of chalcones, flavanones and Schiff bases[J]. Journal of Chinese Pharmaceutical Sciences, 2017, 26(8): 611-620.

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Chemical modification of acetaminophen: PASS assisted in vivo anti-inflammatory activity of chalcones, flavanones and Schiff bases

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