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The application of click chemistry in the synthesis of agents with anticancer activity.

Ma N, Wang Y, Zhao BX, Ye WC, Jiang S - Drug Des Devel Ther (2015)

Bottom Line: The copper(I)-catalyzed 1,3-dipolar cycloaddition between alkynes and azides (click chemistry) to form 1,2,3-triazoles is the most popular reaction due to its reliability, specificity, and biocompatibility.This reaction has the potential to shorten procedures, and render more efficient lead identification and optimization procedures in medicinal chemistry, which is a powerful modular synthetic approach toward the assembly of new molecular entities and has been applied in anticancer drugs discovery increasingly.The present review focuses mainly on the applications of this reaction in the field of synthesis of agents with anticancer activity, which are divided into four groups: topoisomerase II inhibitors, histone deacetylase inhibitors, protein tyrosine kinase inhibitors, and antimicrotubule agents.

View Article: PubMed Central - PubMed

Affiliation: Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, People's Republic of China ; Laboratory of Medicinal Chemistry, Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou, People's Republic of China ; Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, People's Republic of China.

ABSTRACT
The copper(I)-catalyzed 1,3-dipolar cycloaddition between alkynes and azides (click chemistry) to form 1,2,3-triazoles is the most popular reaction due to its reliability, specificity, and biocompatibility. This reaction has the potential to shorten procedures, and render more efficient lead identification and optimization procedures in medicinal chemistry, which is a powerful modular synthetic approach toward the assembly of new molecular entities and has been applied in anticancer drugs discovery increasingly. The present review focuses mainly on the applications of this reaction in the field of synthesis of agents with anticancer activity, which are divided into four groups: topoisomerase II inhibitors, histone deacetylase inhibitors, protein tyrosine kinase inhibitors, and antimicrotubule agents.

No MeSH data available.


Chemical structures of protein tyrosine kinase inhibitors synthesized via click chemistry.
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f14-dddt-9-1585: Chemical structures of protein tyrosine kinase inhibitors synthesized via click chemistry.

Mentions: For studying the evaluation of 1,4-disubstituted 1,2,3-triazoles as a novel template for Src kinase inhibition, Kumar et al hypothesized that substitution at N1 and position 4 of 1,2,3-triazoles with hydrophobic residues may occupy and interact with the hydrophobic-binding pocket of Src ATP-binding site similar to that of 3-phenylpyrazolo-pyrimidines. They synthesized two classes of 1,4-disubstituted 1,2,3-triazoles using one-pot reaction of α-tosyloxy ketones/α-halo ketones in the presence of aqueous polyethylene glycol (1:1, v/v) via the click chemistry approach in 2010. Compounds 25a–25c and 26a and 26b (Figure 14) exhibited modest Src kinase inhibitory activity among the synthesized 1,2,3-triazoles with IC50 values in the range of 32–43 μM. The insertion of C6H5– and 4-CH3C6H4– at the triazole functional group and less bulkier group at the ketone position shows better inhibitory activity for Src kinase.46


The application of click chemistry in the synthesis of agents with anticancer activity.

Ma N, Wang Y, Zhao BX, Ye WC, Jiang S - Drug Des Devel Ther (2015)

Chemical structures of protein tyrosine kinase inhibitors synthesized via click chemistry.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4362898&req=5

f14-dddt-9-1585: Chemical structures of protein tyrosine kinase inhibitors synthesized via click chemistry.
Mentions: For studying the evaluation of 1,4-disubstituted 1,2,3-triazoles as a novel template for Src kinase inhibition, Kumar et al hypothesized that substitution at N1 and position 4 of 1,2,3-triazoles with hydrophobic residues may occupy and interact with the hydrophobic-binding pocket of Src ATP-binding site similar to that of 3-phenylpyrazolo-pyrimidines. They synthesized two classes of 1,4-disubstituted 1,2,3-triazoles using one-pot reaction of α-tosyloxy ketones/α-halo ketones in the presence of aqueous polyethylene glycol (1:1, v/v) via the click chemistry approach in 2010. Compounds 25a–25c and 26a and 26b (Figure 14) exhibited modest Src kinase inhibitory activity among the synthesized 1,2,3-triazoles with IC50 values in the range of 32–43 μM. The insertion of C6H5– and 4-CH3C6H4– at the triazole functional group and less bulkier group at the ketone position shows better inhibitory activity for Src kinase.46

Bottom Line: The copper(I)-catalyzed 1,3-dipolar cycloaddition between alkynes and azides (click chemistry) to form 1,2,3-triazoles is the most popular reaction due to its reliability, specificity, and biocompatibility.This reaction has the potential to shorten procedures, and render more efficient lead identification and optimization procedures in medicinal chemistry, which is a powerful modular synthetic approach toward the assembly of new molecular entities and has been applied in anticancer drugs discovery increasingly.The present review focuses mainly on the applications of this reaction in the field of synthesis of agents with anticancer activity, which are divided into four groups: topoisomerase II inhibitors, histone deacetylase inhibitors, protein tyrosine kinase inhibitors, and antimicrotubule agents.

View Article: PubMed Central - PubMed

Affiliation: Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, People's Republic of China ; Laboratory of Medicinal Chemistry, Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou, People's Republic of China ; Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, People's Republic of China.

ABSTRACT
The copper(I)-catalyzed 1,3-dipolar cycloaddition between alkynes and azides (click chemistry) to form 1,2,3-triazoles is the most popular reaction due to its reliability, specificity, and biocompatibility. This reaction has the potential to shorten procedures, and render more efficient lead identification and optimization procedures in medicinal chemistry, which is a powerful modular synthetic approach toward the assembly of new molecular entities and has been applied in anticancer drugs discovery increasingly. The present review focuses mainly on the applications of this reaction in the field of synthesis of agents with anticancer activity, which are divided into four groups: topoisomerase II inhibitors, histone deacetylase inhibitors, protein tyrosine kinase inhibitors, and antimicrotubule agents.

No MeSH data available.