Synthesis of novel alkyltriazole tagged pyrido[2,3-d]pyrimidine derivatives and their anticancer activity

A series of novel alkyltriazole tagged pyrido[2,3-d]pyrimidine derivatives 5 and 6 was prepared starting from 2,3-active functional pyridine 1 via cyclization, propargylation followed by reaction with alkyl or perfluoroalkyl azides under Sharpless conditions. All the compounds 5 and 6 were screened...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2011-08, Vol.46 (8), p.3462-3468
Main Authors: Kurumurthy, C., Sambasiva Rao, P., Veera swamy, B., Santhosh kumar, G., Shanthan Rao, P., Narsaiah, B., Velatooru, L.R., Pamanji, R., Venkateswara Rao, J.
Format: Article
Language:English
Subjects:
Alkylation
Anticancer activity
Antineoplastic agents
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
Azides - chemistry
Biological and medical sciences
Cell Line, Tumor
Cell Survival - drug effects
Colorectal Neoplasms - drug therapy
Colorectal Neoplasms - pathology
Cyclisation
Cyclization
Drug Screening Assays, Antitumor
General aspects
Humans
Inhibitory Concentration 50
Leukemia, Monocytic, Acute - drug therapy
Leukemia, Monocytic, Acute - pathology
Lymphoma - drug therapy
Lymphoma - pathology
Medical sciences
Perfluoroalkyl azides
Pharmacology. Drug treatments
Propargylation
Pyrido[2,3-d]pyrimidine
Pyrimidines - chemical synthesis
Pyrimidines - pharmacology
Sharpless conditions
Structure-Activity Relationship
Triazoles - chemistry
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Summary:A series of novel alkyltriazole tagged pyrido[2,3-d]pyrimidine derivatives 5 and 6 was prepared starting from 2,3-active functional pyridine 1 via cyclization, propargylation followed by reaction with alkyl or perfluoroalkyl azides under Sharpless conditions. All the compounds 5 and 6 were screened for anticancer activity against three cancer cell lines such as U 937, THP-1 and Colo205. The promising compounds 5b and 5e have been identified. A series of novel alkyltriazole tagged pyrido[2,3-d]pyrimidine derivatives 5 and 6 was prepared, screened for anticancer activity against three cancer cell lines and identified promising compounds 5b and 5e. [Display omitted] ► Sulphuric acid catalysed synthesis of novel pyrido[2,3-d]pyrimidine-4(3H)ones. ► Propargylation to obtain O- and N-propargylated pyrido[2,3-d]pyrimidines. ► Each isomer was reacted with alkyl azide under Sharpless conditions. ► Exclusively 1,4-disubstituted triazole tagged pyrido[2,3-d]pyrimidines formed. ► Final products screened for anticancer activity against three cancer cell lines.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2011.05.011