Naslov
Novel 1,2,3-triazole Derivatives of Benzoxazole: Synthesis, Structural Characterization and Biological Activity

Autori
Ostrički, Robert ; Persoons, Leentje ; Vanstreels, Els ; Daelemans, Dirk ; Gazivoda Kraljević, Tatjana

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
XIV Meeting of Young Chemical Engineers Book of Abstracts / Žižek, Krunoslav ; Katančić, Zvonimir ; Kovačić, Marin - Zagreb : Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI), 2022, 129-129

Skup
XIV. susret mladih kemijskih inženjera (SMLKI 2022)

Mjesto i datum
Zagreb, Hrvatska, 24.02.2022. - 25.02.2022

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
benzoxazole, 1, 2, 3-triazole, click chemistry, antitumor evaluation

Sažetak
Cancer is one of the main causes of death worldwide along with cardiovascular diseases. Due to its high mortality rate and frequency, medicinal chemists are rapidly developing new, potent antitumor agents. Benzoxazoles are structural isosters of natural nucleotides and represent an important class of heterocyclic compounds exhibiting exceptional pharmacological activities such as anticancer, anti-inflammatory and antiviral. In addition, some of them have found application as fluorescent whitening agents and functional materials [1-2]. Utilizing conventional and green synthetic methods, novel derivatives of benzoxazole containing 1, 2, 3-triazole ring as a linker were prepared. Propargylated 2-aminobenzoxazole and 2-thiobenzoxazole were prepared in a two-step reaction including cyclization reaction of 2-aminophenol using di(imidazole-1-yl)methanimine or carbon disulfide, and subsequent N-alkylation reaction with propargyl bromide as an alkylating reagent. 2-amino- and 2-thiobenzoxazole derivatives with 1, 2, 3-triazole moiety were synthesized by Cu(I) catalyzed click reaction of 2-propargylated benzoxazole derivatives with corresponding azides. The most potent activity against acute lymphoblastic leukemia (DND-41, IC50= 1 μM) showed benzoxazole derivative consisting of coumarin ring linked via 1, 2, 3-triazole. [1] C. P. Kaushik, M. Chahal, .J. Chem. Sci. 132 (2020) 142. [2] M. Kale, V. Chavan, Mini-Rev. Org. Chem. 16 (2019) 111

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA