Synthesis, characterization and pharmacological evaluation of substituted phenoxy acetamide derivatives
A novel series of 2-(substituted phenoxy)-N-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)acetamide and N-(2-bromocyclohexyl)-2-(substituted phenoxy)acetamide derivatives having cyclohexyl nucleus as common in both types were synthesized and assessed for their anti-inflammatory activity by a...
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Association of Chemical Engineers of Serbia
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doaj-d405dec36b9e4c978e273b1102e7bbf22020-11-24T21:35:41ZengAssociation of Chemical Engineers of SerbiaHemijska Industrija 0367-598X2217-74262015-01-0169440541510.2298/HEMIND140330057R0367-598X1400057RSynthesis, characterization and pharmacological evaluation of substituted phenoxy acetamide derivativesRani Priyanka0Pal Dilip Kumar1Hegde Rahul Rama2Hashim Syed Riaz3IFTM University Moradabad, School of Sciences, Department of Chemistry, Uttar Pradesh, IndiaGuru Ghasidas Viswavidyalaya, Institute of Pharmaceutical Sciences, Department of Chemistry, Bilaspur, Chhattisgarh, IndiaIFTM University Moradabad, Department of Pharmaceutics, School of Pharmaceutical Sciences, Uttar Pradesh, IndiaSenior Author and Retired Professor Department of Chemistry, School of Pharmaceutical Sciences, IFTM University Moradabad, Uttar Pradesh, IndiaA novel series of 2-(substituted phenoxy)-N-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)acetamide and N-(2-bromocyclohexyl)-2-(substituted phenoxy)acetamide derivatives having cyclohexyl nucleus as common in both types were synthesized and assessed for their anti-inflammatory activity by a carrageenan induced rat paw oedema method, analgesic activity by Eddy’s hot plate method and antipyretic activity by brewer’s yeast induced pyrexia method. All the novel derivatives have been synthesized by the reaction of camphor and similar ketone having cyclohexane nucleus (e.g. 2-bromocyclohexanone) with ammonium carbonate and formic acid resulting in the formation of aromatic amines (1a-b). These amines on further chloroacetylation with chloroacetylchloride give compounds (2a-b). Compounds (2a-b) are converted to 2-(substituted phenoxy)-N-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl) acetamide and N-(2-bromocyclohexyl)-2-(substituted phenoxy)acetamide derivatives on treatment with substituted phenol. Among the series 3a-f, 3i, 3k, 3l compounds showed significant anti-inflammatory activity as compared to the standard drug diclofenac sodium and also compound 3a-f, 3h, 3j, 3k exhibit significant analgesic activity as compared to the standard drug. Compounds 3a-f and 3k showed antipyretic activity nearly to the standard drug indomethacin. Compounds 3a-f and 3k possess anti-inflammatory, analgesic and antipyretic activities near to the standard.http://www.doiserbia.nb.rs/img/doi/0367-598X/2015/0367-598X1400057R.pdf2-(substituted phenoxy)-N-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)acetamideN-(2-bromocyclohexyl)-2-(substituted phenoxy)acetamideanti-inflammatory activityanalgesic activityantipyretic activity |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Rani Priyanka Pal Dilip Kumar Hegde Rahul Rama Hashim Syed Riaz |
spellingShingle |
Rani Priyanka Pal Dilip Kumar Hegde Rahul Rama Hashim Syed Riaz Synthesis, characterization and pharmacological evaluation of substituted phenoxy acetamide derivatives Hemijska Industrija 2-(substituted phenoxy)-N-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)acetamide N-(2-bromocyclohexyl)-2-(substituted phenoxy)acetamide anti-inflammatory activity analgesic activity antipyretic activity |
author_facet |
Rani Priyanka Pal Dilip Kumar Hegde Rahul Rama Hashim Syed Riaz |
author_sort |
Rani Priyanka |
title |
Synthesis, characterization and pharmacological evaluation of substituted phenoxy acetamide derivatives |
title_short |
Synthesis, characterization and pharmacological evaluation of substituted phenoxy acetamide derivatives |
title_full |
Synthesis, characterization and pharmacological evaluation of substituted phenoxy acetamide derivatives |
title_fullStr |
Synthesis, characterization and pharmacological evaluation of substituted phenoxy acetamide derivatives |
title_full_unstemmed |
Synthesis, characterization and pharmacological evaluation of substituted phenoxy acetamide derivatives |
title_sort |
synthesis, characterization and pharmacological evaluation of substituted phenoxy acetamide derivatives |
publisher |
Association of Chemical Engineers of Serbia |
series |
Hemijska Industrija |
issn |
0367-598X 2217-7426 |
publishDate |
2015-01-01 |
description |
A novel series of 2-(substituted
phenoxy)-N-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)acetamide and
N-(2-bromocyclohexyl)-2-(substituted phenoxy)acetamide derivatives having
cyclohexyl nucleus as common in both types were synthesized and assessed for
their anti-inflammatory activity by a carrageenan induced rat paw oedema
method, analgesic activity by Eddy’s hot plate method and antipyretic
activity by brewer’s yeast induced pyrexia method. All the novel derivatives
have been synthesized by the reaction of camphor and similar ketone having
cyclohexane nucleus (e.g. 2-bromocyclohexanone) with ammonium carbonate and
formic acid resulting in the formation of aromatic amines (1a-b). These
amines on further chloroacetylation with chloroacetylchloride give compounds
(2a-b). Compounds (2a-b) are converted to 2-(substituted
phenoxy)-N-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl) acetamide and
N-(2-bromocyclohexyl)-2-(substituted phenoxy)acetamide derivatives on
treatment with substituted phenol. Among the series 3a-f, 3i, 3k, 3l
compounds showed significant anti-inflammatory activity as compared to the
standard drug diclofenac sodium and also compound 3a-f, 3h, 3j, 3k exhibit
significant analgesic activity as compared to the standard drug. Compounds
3a-f and 3k showed antipyretic activity nearly to the standard drug
indomethacin. Compounds 3a-f and 3k possess anti-inflammatory, analgesic and
antipyretic activities near to the standard. |
topic |
2-(substituted phenoxy)-N-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)acetamide N-(2-bromocyclohexyl)-2-(substituted phenoxy)acetamide anti-inflammatory activity analgesic activity antipyretic activity |
url |
http://www.doiserbia.nb.rs/img/doi/0367-598X/2015/0367-598X1400057R.pdf |
work_keys_str_mv |
AT ranipriyanka synthesischaracterizationandpharmacologicalevaluationofsubstitutedphenoxyacetamidederivatives AT paldilipkumar synthesischaracterizationandpharmacologicalevaluationofsubstitutedphenoxyacetamidederivatives AT hegderahulrama synthesischaracterizationandpharmacologicalevaluationofsubstitutedphenoxyacetamidederivatives AT hashimsyedriaz synthesischaracterizationandpharmacologicalevaluationofsubstitutedphenoxyacetamidederivatives |
_version_ |
1725944521766731776 |