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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 topoisomerase II inhibitors synthesized via click chemistry.
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f2-dddt-9-1585: Chemical structures of topoisomerase II inhibitors synthesized via click chemistry.

Mentions: Mansonones17,18 are quinone-containing compounds that show good anticancer activities. To investigate the effects of C-9 halogenation and C-3 substitution on mansonone E, Huang et al synthesized two series of novel C-9 chloro- and bromo-substituted mansonone E derivatives with triazole moieties at the C-3 position, which were prepared by using click chemistry. Structure-activity relationship study revealed that the substituent at the C-9 position and the triazole ring exhibited various influences on the cytotoxicity against several human cancer cell lines. Topo II inhibition assay indicated that almost all of the C-9 bromo-substituted derivatives showed better activities than the C-9 chloro-substituted derivatives. The cytotoxic activities of these compounds against A-549, HL-60, K562, and HeLa cells were also evaluated by comparing with etoposide, which was used as a positive control. The result indicated that these compounds (3a–3d, Figure 2) have the potential to be antitumor agents as topoisomerase II inhibitors.19


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 topoisomerase II inhibitors synthesized via click chemistry.
© Copyright Policy
Related In: Results  -  Collection

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

f2-dddt-9-1585: Chemical structures of topoisomerase II inhibitors synthesized via click chemistry.
Mentions: Mansonones17,18 are quinone-containing compounds that show good anticancer activities. To investigate the effects of C-9 halogenation and C-3 substitution on mansonone E, Huang et al synthesized two series of novel C-9 chloro- and bromo-substituted mansonone E derivatives with triazole moieties at the C-3 position, which were prepared by using click chemistry. Structure-activity relationship study revealed that the substituent at the C-9 position and the triazole ring exhibited various influences on the cytotoxicity against several human cancer cell lines. Topo II inhibition assay indicated that almost all of the C-9 bromo-substituted derivatives showed better activities than the C-9 chloro-substituted derivatives. The cytotoxic activities of these compounds against A-549, HL-60, K562, and HeLa cells were also evaluated by comparing with etoposide, which was used as a positive control. The result indicated that these compounds (3a–3d, Figure 2) have the potential to be antitumor agents as topoisomerase II inhibitors.19

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.