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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 histone deacetylase inhibitors synthesized via click chemistry.Abbreviations: HDAC, histone deacetylases; SAHA, suberoylanilide hydroxamic acid.
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f6-dddt-9-1585: Chemical structures of histone deacetylase inhibitors synthesized via click chemistry.Abbreviations: HDAC, histone deacetylases; SAHA, suberoylanilide hydroxamic acid.

Mentions: Chen et al established a 1,2,3-triazole ring as a surface recognition cap group-linking moiety in SAHA-like HDA-CIs. They synthesized several triazole-linked SAHA-like hydroxamates using click chemistry in 2008. In these compounds, the amide bond in SAHA was replaced with a triazole ring. The linker chain length and the aromatic ring of these compounds were both varied. Several compounds (10a–10e, Figure 6) have showed potent inhibition of HDACs.29


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 histone deacetylase inhibitors synthesized via click chemistry.Abbreviations: HDAC, histone deacetylases; SAHA, suberoylanilide hydroxamic acid.
© Copyright Policy
Related In: Results  -  Collection

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

f6-dddt-9-1585: Chemical structures of histone deacetylase inhibitors synthesized via click chemistry.Abbreviations: HDAC, histone deacetylases; SAHA, suberoylanilide hydroxamic acid.
Mentions: Chen et al established a 1,2,3-triazole ring as a surface recognition cap group-linking moiety in SAHA-like HDA-CIs. They synthesized several triazole-linked SAHA-like hydroxamates using click chemistry in 2008. In these compounds, the amide bond in SAHA was replaced with a triazole ring. The linker chain length and the aromatic ring of these compounds were both varied. Several compounds (10a–10e, Figure 6) have showed potent inhibition of HDACs.29

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.