2-((1H-1,2,3-triazol-1-yl)methyl)-3-phenylquinazolin-4(3H)-ones: Design, Synthesis and Evaluation as Anti-cancer Agents

Author(s): Kamala K. Vasu*, Hemantkumar D. Ingawale, Sneha R. Sagar, Jayesh A. Sharma, Dhaivat H. Pandya, Milee Agarwal.

Journal Name: Current Bioactive Compounds

Volume 14 , Issue 3 , 2018

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Abstract:

Background: Prevalence of lung cancer and breast cancer is increasing worldwide. Current therapies have certain limitations for the treatment of lung cancer and breast cancer. We herewith report a series of novel 2-((1H-1,2,3-triazol-1-yl)methyl)-3-phenylquinazolin-4(3H)-ones as anticancer agents for the treatment of lung cancer and breast cancer.

Method: Synthesis of 2-((1H-1,2,3-triazol-1-yl)methyl)-3-phenylquinazolin-4(3H)-ones involves four steps. Step 1 is the formation of 2-(2-chloroacetamido)benzoic acid from 2-aminobenzoic acid by coupling with 2-chloroacetyl chloride, followed by step 2 which involves the formation of quinazolinone ring scaffold 2-(chloromethyl)-3-phenylquinazolin-4(3H)-ones on cyclisation with substituted anilines. Step 3 and 4 follow click chemistry approach of Huisgen's 1,3-dipolar cycloaddition which include conversion to 2-(azidomethyl)-3-phenylquinazolin-4(3H)-ones by sodium azide and further reaction with substituted alkynes to obtain 2-((1H-1,2,3-triazol-1-yl)methyl)-3-phenylquinazolin- 4(3H)-ones. All the molecules are characterized by spectral analysis and tested for anti-cancer activity against A-549 lung cancer and MDAMB-231 breast cancer cell lines using colorimetric MTT assay.

Results: Amongst the synthesized compounds, 3-(4-nitrophenyl)-2-((4-phenyl-1H-1,2,3-triazol-1- yl)methyl)quinazoline-4-(3H)-one 5i and 3-(2,4-Dimethoxyphenyl)-2-((4-phenyl-1H-1,2,3-triazol-1- yl)methyl)quinazoline-4(3H)-one 5o were found to be active based on cell viability assays using A- 549 lung and MDAMB-231 breast cancer cell lines.

Conclusion: Novel route for the synthesis of hitherto unknown 2-((1H-1,2,3-triazol-1-yl)methyl)-3- phenylquinazolin-4(3H)-ones was developed. All the molecules were tested for their anti-cancer activities and two molecules were shown to exhibit anti-cancer activity in micromolar range.

Keywords: Click-chemistry, 1, 2, 3-Triazole, Quinazoline-4(3H)-one, 2-((1H-1, 2, 3-triazol-1-yl)methyl)-3-phenylquinazolin- 4(3H)-one, anti-cancer activity.

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Article Details

VOLUME: 14
ISSUE: 3
Year: 2018
Page: [254 - 263]
Pages: 10
DOI: 10.2174/1573407213666170329131557
Price: $58

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