Akademik Veri Yönetim Sistemi
8th International Bahçeşehir University (BAU) Drug Design Congress, İstanbul, Türkiye, 15 - 17 Aralık 2022, ss.1
Introduction:
Coumarin derivatives are natural
or synthetic heterocyclic molecules with oxygen. They are considered as
pharmacological flavonoids. Coumarin derivatives have attracted researchers’
attention due to their wide range of biological activity such as antitumor,
anticoagulant, antioxidant, antiviral, antiinflamatory, antimicrobial,
antibacterial, etc [1,2].
Triazoles can be used as binders
on the peptides or aromatic rings and
may exert bioisosteric effects. They can bind to a biological target with a
high affinity by hydrogen bonding, dipole-dipole and π-stacking interactions. This
demonstrates the unquestionable importance of triazoles in pharmaceutical
chemistry [3].
Recently, medicinal chemists have
focused on combination of two or more pharmacophores in one molecule to produce
an hybrid molecule. These hybrid molecules can show enhanced or even new
biological activities.
Method:
After the synthesis of the
coumarin skeleton, alkylation reactions on the 5- and 7-positions of the
coumarin skeleton were performed. Then, the synthesis of azide derivatives was
carried out by the reaction of obtained alkylation products with NaN3.
Finally, 1,2,3-triazole ring was obtained by click reaction of synthesized
azide derivatives and dipolarophils.
Result and Discussion:
Coumarin ring formation and
alkylation reactions were performed by well known and easily applicable
methods. To construct the 1,2,3-trizole rings, click reactions were
accomplished under mild conditions in good yields. The structures of all new coumarin-bistrizole
hybrides were confirmed by their spectral data.
Conclusion:
In conclusion, a serie of new coumarin-bistriazole derivatives with the potential to display a variety of biological activities have been designed and synthesized.
Keywords: Coumarin, triazole, biological activity, heterocyclic compound, organic synthesis
This work was
supported by Yildiz Technical University Scientific Research Foundation
[project number FDK-2021-4263].
References:
[1] O.
Kayser, H. Kolodziej, Antibacterial
Activity of Simple Coumarins: Structural Requirements for Biological Activity, Z. Naturforsch. 1999, 54c, 169-174.
[2] L.Wu, X. Wang, W. Xu, F. Farzaneh, R. Xu, The structure and pharmacological functions of coumarins and their derivatives, Cur. Med. Chem. 2009, 16, 4236-4260.
[3] Dheer, D., Singh, V.,
&Shankar, R. (2017). ‘‘Medicinal attributes of 1, 2, 3-triazoles: Current
developments’’, Bioorganic Chemistry, 71, 30-54.