Limits...
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.
© Copyright Policy
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4362898&req=5

f11-dddt-9-1585: Chemical structures of histone deacetylase inhibitors synthesized via click chemistry.Abbreviations: HDAC, histone deacetylases; SAHA, suberoylanilide hydroxamic acid.

Mentions: Largazole 3 was a natural macrocyclic depsipeptide reported by Taori et al in 2008, which showed promising HDAC1 inhibitory activity and selectivity.37 Li et al replaced the 4-methylthiazoline moiety of largazole with nitrogen functionality via click chemistry and obtained a series of new largazole analogs (22, Figure 11), which showed good selectivity for HDAC1 (IC50 =0.1 μM) over HDAC9 (IC50 = 34.6 μM) compared to largazole in 2012. The experimental results also indicated that the introduction of appropriate aromatic groups into the largazole skeleton was a useful optimizing tool for this unique class of anticancer agents.38


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

f11-dddt-9-1585: Chemical structures of histone deacetylase inhibitors synthesized via click chemistry.Abbreviations: HDAC, histone deacetylases; SAHA, suberoylanilide hydroxamic acid.
Mentions: Largazole 3 was a natural macrocyclic depsipeptide reported by Taori et al in 2008, which showed promising HDAC1 inhibitory activity and selectivity.37 Li et al replaced the 4-methylthiazoline moiety of largazole with nitrogen functionality via click chemistry and obtained a series of new largazole analogs (22, Figure 11), which showed good selectivity for HDAC1 (IC50 =0.1 μM) over HDAC9 (IC50 = 34.6 μM) compared to largazole in 2012. The experimental results also indicated that the introduction of appropriate aromatic groups into the largazole skeleton was a useful optimizing tool for this unique class of anticancer agents.38

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.