Synthesis, Antioxidant, Antinociceptive Activity of Novel Phenoxy acetyl carboxamides
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Published:2022-06-30
Issue:3
Volume:38
Page:709-717
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ISSN:2231-5039
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Container-title:Oriental Journal Of Chemistry
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language:en
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Short-container-title:Orient. J. Chem
Author:
Manjusha R. K.1, M. Reddemma M. Reddemma1, Begum Shaheen2ORCID, Begum Sk Arifa3ORCID, Shareef Mohammad Zubair4, K.Bharathi K.Bharathi2ORCID
Affiliation:
1. 1Department of Pharmaceutical Chemistry/ Sree Vidyanikethan College of Pharmacy, Tirupati-517102, Andhra Pradesh, India. 2. 2Institute of Pharmaceutical Technology, Sri Padmavati Mahila Visvavidyalayam, Tirupati, 517102, Andhra Pradesh, India. 3. 3Bharat Institute of Technology, Affi JNTU H,Mangalpally, Ranga Reddy, Hyderabad, Telangana, India. 4. 4Department of Pharmacology, Sri Shivani College of Pharmacy, Warangal - 506007, Telangana, India.
Abstract
A series of novel phenoxy acetyl carboxamides (4a-4g) were synthesized by amidation using phenoxy acetyl hydrazide and various acid chlorides (benzoyl, adamantly carbonyl cinnamoyl, 4-chloro benzoyl chlorides) or bases (piperidine, morpholine & substituted piperidinone) and evaluated for antioxidant and antinociceptive activities. The title compounds were purified by recrystallization using ethanol and characterized by spectral (FTIR, 1H NMR, and Mass) analysis. Compound 4a was effective in scavenging the DPPH radicals (57%) and nitric oxide (NO) radicals (52%) while compound 4e was able to significantly neutralize ABTS cation radicals (58%). However, the radical scavenging ability was lesser compared to the standard antioxidant agents. Among the tested compounds, 4f and 4g elicited good antinociceptive activity in the central and peripheral animal models (25 mg/kg body weight). Compounds 4b and 4f seem to open ATP-sensitive potassium channels (KATP channels), a possible mechanism for their peripheral effects. The carboxamides bind well with the monoglyceride lipase enzyme (MAGL) and established strong interactions at the active site.
Publisher
Oriental Scientific Publishing Company
Subject
Drug Discovery,Environmental Chemistry,Biochemistry,General Chemistry
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