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Anticancer, anti-inflammatory, and analgesic activities of synthesized 2-(substituted phenoxy) acetamide derivatives.

Rani P, Pal D, Hegde RR, Hashim SR - Biomed Res Int (2014)

Bottom Line: These investigations revealed that synthesized products 3a-j with halogens on the aromatic ring favors as the anticancer and anti-inflammatory activity.Among all, compound 3c N-(1-(4-chlorophenyl)ethyl)-2-(4-nitrophenoxy)acetamide exhibited anticancer, anti-inflammatory, and analgesic activities.In conclusion, 3c may have potential to be developed into a therapeutic agent.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, School of Sciences, IFTM University, Moradabad, Uttar Pradesh, India.

ABSTRACT
The aphorism was to develop new chemical entities as potential anticancer, anti-inflammatory, and analgesic agents. The Leuckart synthetic pathway was utilized in development of novel series of 2-(substituted phenoxy)-N-(1-phenylethyl)acetamide derivatives. The compounds containing 1-phenylethylamine as basic moiety attached to substituted phenols were assessed for their anticancer activity against MCF-7 (breast cancer), SK-N-SH (neuroblastoma), anti-inflammatory activity, and analgesic activity. These investigations revealed that synthesized products 3a-j with halogens on the aromatic ring favors as the anticancer and anti-inflammatory activity. Among all, compound 3c N-(1-(4-chlorophenyl)ethyl)-2-(4-nitrophenoxy)acetamide exhibited anticancer, anti-inflammatory, and analgesic activities. In conclusion, 3c may have potential to be developed into a therapeutic agent.

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General structure of the synthesized compounds.
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fig2: General structure of the synthesized compounds.

Mentions: A series of titled derivatives N-(1-(4-chlorophenyl)ethyl)-2-(substituted phenoxy)acetamide 3(a–e) derivatives and 2-(substituted phenoxy)-N-(1-(p-tolyl)ethyl)acetamide 3(f–j) derivatives (Figures 2 and 3) was synthesized as per scheme. 1-(4-chlorophenyl)ethanone and 1-(p-tolyl)ethanone were separately treated with ammonium carbonate and formic acid resulting in the formation of amines 1a and 1b, respectively. These amines on chloroacetylation with chloroacetyl chloride at 0°C in 10% sodium hydroxide medium give chloro compounds 2a and 2b which converted to (3a–j) by the reaction with different substituted phenols in presence of potassium iodide and potassium carbonate in dry acetone as a solvent. The structure of newly synthesized compounds (Figures 2 and 3) was confirmed by spectral data (IR, 1H NMR, 13C-NMR and mass); Table 1 shows the physical data of compounds (3a–j).


Anticancer, anti-inflammatory, and analgesic activities of synthesized 2-(substituted phenoxy) acetamide derivatives.

Rani P, Pal D, Hegde RR, Hashim SR - Biomed Res Int (2014)

General structure of the synthesized compounds.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4150437&req=5

fig2: General structure of the synthesized compounds.
Mentions: A series of titled derivatives N-(1-(4-chlorophenyl)ethyl)-2-(substituted phenoxy)acetamide 3(a–e) derivatives and 2-(substituted phenoxy)-N-(1-(p-tolyl)ethyl)acetamide 3(f–j) derivatives (Figures 2 and 3) was synthesized as per scheme. 1-(4-chlorophenyl)ethanone and 1-(p-tolyl)ethanone were separately treated with ammonium carbonate and formic acid resulting in the formation of amines 1a and 1b, respectively. These amines on chloroacetylation with chloroacetyl chloride at 0°C in 10% sodium hydroxide medium give chloro compounds 2a and 2b which converted to (3a–j) by the reaction with different substituted phenols in presence of potassium iodide and potassium carbonate in dry acetone as a solvent. The structure of newly synthesized compounds (Figures 2 and 3) was confirmed by spectral data (IR, 1H NMR, 13C-NMR and mass); Table 1 shows the physical data of compounds (3a–j).

Bottom Line: These investigations revealed that synthesized products 3a-j with halogens on the aromatic ring favors as the anticancer and anti-inflammatory activity.Among all, compound 3c N-(1-(4-chlorophenyl)ethyl)-2-(4-nitrophenoxy)acetamide exhibited anticancer, anti-inflammatory, and analgesic activities.In conclusion, 3c may have potential to be developed into a therapeutic agent.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, School of Sciences, IFTM University, Moradabad, Uttar Pradesh, India.

ABSTRACT
The aphorism was to develop new chemical entities as potential anticancer, anti-inflammatory, and analgesic agents. The Leuckart synthetic pathway was utilized in development of novel series of 2-(substituted phenoxy)-N-(1-phenylethyl)acetamide derivatives. The compounds containing 1-phenylethylamine as basic moiety attached to substituted phenols were assessed for their anticancer activity against MCF-7 (breast cancer), SK-N-SH (neuroblastoma), anti-inflammatory activity, and analgesic activity. These investigations revealed that synthesized products 3a-j with halogens on the aromatic ring favors as the anticancer and anti-inflammatory activity. Among all, compound 3c N-(1-(4-chlorophenyl)ethyl)-2-(4-nitrophenoxy)acetamide exhibited anticancer, anti-inflammatory, and analgesic activities. In conclusion, 3c may have potential to be developed into a therapeutic agent.

Show MeSH
Related in: MedlinePlus