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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.Abbreviation: HER, human epidermal growth factor receptor.
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f17-dddt-9-1585: Chemical structures of protein tyrosine kinase inhibitors synthesized via click chemistry.Abbreviation: HER, human epidermal growth factor receptor.

Mentions: The 1,2,3-triazole was discovered as an inhibitor of HER2 tyrosine kinase through computer-aided drug design approach and searched from molecular libraries by Cheng et al. In 2007, Cheng et al synthesized a series of 4-aryl-5-cyano-2-H-1,2,3-triazole derivatives bearing a variety of groups at the 4-position of phenyl by click chemistry. The derivatives showed bioactivity at HER2 tyrosine kinase. Compound 31 (Figure 17) has the lowest IC50 value of 6.6 μM for inhibiting HER2 tyrosine kinase phosphorylation in breast cancer cells and the IC50 value of 30.9 μM for breast cancer MDA-MB-453 cell growth inhibition.59


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.Abbreviation: HER, human epidermal growth factor receptor.
© Copyright Policy
Related In: Results  -  Collection

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

f17-dddt-9-1585: Chemical structures of protein tyrosine kinase inhibitors synthesized via click chemistry.Abbreviation: HER, human epidermal growth factor receptor.
Mentions: The 1,2,3-triazole was discovered as an inhibitor of HER2 tyrosine kinase through computer-aided drug design approach and searched from molecular libraries by Cheng et al. In 2007, Cheng et al synthesized a series of 4-aryl-5-cyano-2-H-1,2,3-triazole derivatives bearing a variety of groups at the 4-position of phenyl by click chemistry. The derivatives showed bioactivity at HER2 tyrosine kinase. Compound 31 (Figure 17) has the lowest IC50 value of 6.6 μM for inhibiting HER2 tyrosine kinase phosphorylation in breast cancer cells and the IC50 value of 30.9 μM for breast cancer MDA-MB-453 cell growth inhibition.59

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.