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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: EGFR, epidermal growth factor receptor.
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f19-dddt-9-1585: Chemical structures of protein tyrosine kinase inhibitors synthesized via click chemistry.Abbreviation: EGFR, epidermal growth factor receptor.

Mentions: To facilitate clinical evaluation of primary tumors and/or metastases using the EGFR-specific imaging agent, Pisaneschi et al synthesized a small array of fluorine-containing compounds based on a 3-cyanoquinoline core in 2010. Compound 33 (Figure 19), incorporating 20-fluoroethyl-1,2,3-triazole, was selected for evaluation as a radioligand based on its high affinity for EGFR kinase (IC50 =1.81±0.18 nM), good cellular potency (IC50 =21.97±9.06 nM), low lipophilicity, and good metabolic stability. Experimental data of the compound showed good stability in vivo and a fourfold higher uptake in high EGFR-expressing A431 tumor xenografts compared to low EGFR-expressing HCT-116 tumor xenografts.61


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: EGFR, epidermal growth factor receptor.
© Copyright Policy
Related In: Results  -  Collection

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

f19-dddt-9-1585: Chemical structures of protein tyrosine kinase inhibitors synthesized via click chemistry.Abbreviation: EGFR, epidermal growth factor receptor.
Mentions: To facilitate clinical evaluation of primary tumors and/or metastases using the EGFR-specific imaging agent, Pisaneschi et al synthesized a small array of fluorine-containing compounds based on a 3-cyanoquinoline core in 2010. Compound 33 (Figure 19), incorporating 20-fluoroethyl-1,2,3-triazole, was selected for evaluation as a radioligand based on its high affinity for EGFR kinase (IC50 =1.81±0.18 nM), good cellular potency (IC50 =21.97±9.06 nM), low lipophilicity, and good metabolic stability. Experimental data of the compound showed good stability in vivo and a fourfold higher uptake in high EGFR-expressing A431 tumor xenografts compared to low EGFR-expressing HCT-116 tumor xenografts.61

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.