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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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The commonly used structures (1a, 1b 2-Phenoxy-N-phenylacetamide core nucleus with antimycobacterial activity) (1c phenoxy-N-phenylacetamide compounds with potent P-gp inhibitor activities).
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fig1: The commonly used structures (1a, 1b 2-Phenoxy-N-phenylacetamide core nucleus with antimycobacterial activity) (1c phenoxy-N-phenylacetamide compounds with potent P-gp inhibitor activities).

Mentions: In the present paper a novel and efficient strategy has been developed to synthesize N-(1-(4-chlorophenyl) ethyl)-2-(substituted phenoxy)acetamide derivatives and 2-(substituted phenoxy)-N-(1-(p-tolyl)ethyl)acetamide derivatives with excellent yields. This synthetic pathway was established by the Leuckart reaction. The Leuckart reaction is a process for the reductive amination of aldehydes and ketones by formamide, ammonium formate, or formic acid with formamide [9]. This reaction has been used for the aromatic compounds, but very little work has been reported for the synthesis of aliphatic compounds (synthesis of 2-heptylamine, propylamine, and isopropylamine) [10]. Apart from the aliphatic compounds, 1,4-benzodiazepines were synthesized by the Leuckart Wallach reaction containing the benzodiazepine scaffold and were originated with various biological activities (benzodiazepine family) comprised mainly of central nervous system (CNS) suppressant due to its anxiolytic, anticonvulsant, sedative, and muscle relaxant activities. It is used in various marketed drugs such as alprazolam, bromazepam, chlorazepate, and valium [11]. 1,4-Benzodiazepines also demonstrate therapeutic activities and are used as antibiotics [12], antiulcers [13], and anti-HIV agents [14]. They are also used as farnesyltransferase inhibitors [15]. Compounds with 2-phenoxy-N-phenylacetamide core nucleus as in Figure 1 (1a and 1b) have shown remarkable research and demonstrated a variety of biological activities such as antimycobacterial [16], antiparasitic [17], antiviral [18], and anticancer [19]activities [20–23]. These compounds are also reported with inhibition of Pgp efflux transporters which are beneficial in the treatment of multidrug resistant strains of cancer cells. The phenoxy-N-phenylacetamide compounds are reported to be less toxic and more effective as that of potent P-gp inhibitors (coumarin analogues, 2-adamantyl analogues); see Figure 1 (1c) [24]. Now, we are reporting a new series of agents that have potent anticancer activities. These agents possibly may act upon COX/LOX pathways which may be included as a part of our future research program.


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)

The commonly used structures (1a, 1b 2-Phenoxy-N-phenylacetamide core nucleus with antimycobacterial activity) (1c phenoxy-N-phenylacetamide compounds with potent P-gp inhibitor activities).
© Copyright Policy
Related In: Results  -  Collection

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

fig1: The commonly used structures (1a, 1b 2-Phenoxy-N-phenylacetamide core nucleus with antimycobacterial activity) (1c phenoxy-N-phenylacetamide compounds with potent P-gp inhibitor activities).
Mentions: In the present paper a novel and efficient strategy has been developed to synthesize N-(1-(4-chlorophenyl) ethyl)-2-(substituted phenoxy)acetamide derivatives and 2-(substituted phenoxy)-N-(1-(p-tolyl)ethyl)acetamide derivatives with excellent yields. This synthetic pathway was established by the Leuckart reaction. The Leuckart reaction is a process for the reductive amination of aldehydes and ketones by formamide, ammonium formate, or formic acid with formamide [9]. This reaction has been used for the aromatic compounds, but very little work has been reported for the synthesis of aliphatic compounds (synthesis of 2-heptylamine, propylamine, and isopropylamine) [10]. Apart from the aliphatic compounds, 1,4-benzodiazepines were synthesized by the Leuckart Wallach reaction containing the benzodiazepine scaffold and were originated with various biological activities (benzodiazepine family) comprised mainly of central nervous system (CNS) suppressant due to its anxiolytic, anticonvulsant, sedative, and muscle relaxant activities. It is used in various marketed drugs such as alprazolam, bromazepam, chlorazepate, and valium [11]. 1,4-Benzodiazepines also demonstrate therapeutic activities and are used as antibiotics [12], antiulcers [13], and anti-HIV agents [14]. They are also used as farnesyltransferase inhibitors [15]. Compounds with 2-phenoxy-N-phenylacetamide core nucleus as in Figure 1 (1a and 1b) have shown remarkable research and demonstrated a variety of biological activities such as antimycobacterial [16], antiparasitic [17], antiviral [18], and anticancer [19]activities [20–23]. These compounds are also reported with inhibition of Pgp efflux transporters which are beneficial in the treatment of multidrug resistant strains of cancer cells. The phenoxy-N-phenylacetamide compounds are reported to be less toxic and more effective as that of potent P-gp inhibitors (coumarin analogues, 2-adamantyl analogues); see Figure 1 (1c) [24]. Now, we are reporting a new series of agents that have potent anticancer activities. These agents possibly may act upon COX/LOX pathways which may be included as a part of our future research program.

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