hrcak mascot   Srce   HID

Izvorni znanstveni članak
https://doi.org/10.5562/cca3165

Synthesis, Cytostatic and Antibacterial Evaluations of Novel 1,2,3-Triazolyl-tagged Pyrimidine and Furo[2,3-d]pyrimidine Derivatives

Maja Stipković Babić ; Department of Organic Chemistry, Faculty of Chemical Engeneering and Technology, University of Zagreb, Marulićev trg 20, HR-10000 Zagreb, Croatia
Ana Ratković ; Department of Organic Chemistry, Faculty of Chemical Engeneering and Technology, University of Zagreb, Marulićev trg 20, HR-10000 Zagreb, Croatia
Marijana Jukić ; Department of Medicinal Chemistry, Biochemistry and Clinical Chemistry, Faculty of Medicine, J. J. Strossmayer University of Osijek, Huttlerova 4, HR-31000 Osijek, Croatia
Ljubica Glavaš-Obrovac ; Department of Medicinal Chemistry, Biochemistry and Clinical Chemistry, Faculty of Medicine, J. J. Strossmayer University of Osijek, Huttlerova 4, HR-31000 Osijek, Croatia
Domagoj Drenjančević ; Department of Microbiology and Parasitology, Faculty of Medicine, J. J. Strossmayer University of Osijek, Huttlerova 4, HR-31000 Osijek, Croatia
Silvana Raić-Malić ; Department of Organic Chemistry, Faculty of Chemical Engeneering and Technology, University of Zagreb, Marulićev trg 20, HR-10000 Zagreb, Croatia
Tatjana Gazivoda Kraljević ; Department of Organic Chemistry, Faculty of Chemical Engeneering and Technology, University of Zagreb, Marulićev trg 20, HR-10000 Zagreb, Croatia

Puni tekst: engleski, pdf (2 MB) str. 197-205 preuzimanja: 837* citiraj
APA 6th Edition
Stipković Babić, M., Ratković, A., Jukić, M., Glavaš-Obrovac, Lj., Drenjančević, D., Raić-Malić, S. i Gazivoda Kraljević, T. (2017). Synthesis, Cytostatic and Antibacterial Evaluations of Novel 1,2,3-Triazolyl-tagged Pyrimidine and Furo[2,3-d]pyrimidine Derivatives. Croatica Chemica Acta, 90 (2), 197-205. https://doi.org/10.5562/cca3165
MLA 8th Edition
Stipković Babić, Maja, et al. "Synthesis, Cytostatic and Antibacterial Evaluations of Novel 1,2,3-Triazolyl-tagged Pyrimidine and Furo[2,3-d]pyrimidine Derivatives." Croatica Chemica Acta, vol. 90, br. 2, 2017, str. 197-205. https://doi.org/10.5562/cca3165. Citirano 02.03.2021.
Chicago 17th Edition
Stipković Babić, Maja, Ana Ratković, Marijana Jukić, Ljubica Glavaš-Obrovac, Domagoj Drenjančević, Silvana Raić-Malić i Tatjana Gazivoda Kraljević. "Synthesis, Cytostatic and Antibacterial Evaluations of Novel 1,2,3-Triazolyl-tagged Pyrimidine and Furo[2,3-d]pyrimidine Derivatives." Croatica Chemica Acta 90, br. 2 (2017): 197-205. https://doi.org/10.5562/cca3165
Harvard
Stipković Babić, M., et al. (2017). 'Synthesis, Cytostatic and Antibacterial Evaluations of Novel 1,2,3-Triazolyl-tagged Pyrimidine and Furo[2,3-d]pyrimidine Derivatives', Croatica Chemica Acta, 90(2), str. 197-205. https://doi.org/10.5562/cca3165
Vancouver
Stipković Babić M, Ratković A, Jukić M, Glavaš-Obrovac Lj, Drenjančević D, Raić-Malić S i sur. Synthesis, Cytostatic and Antibacterial Evaluations of Novel 1,2,3-Triazolyl-tagged Pyrimidine and Furo[2,3-d]pyrimidine Derivatives. Croatica Chemica Acta [Internet]. 2017 [pristupljeno 02.03.2021.];90(2):197-205. https://doi.org/10.5562/cca3165
IEEE
M. Stipković Babić, et al., "Synthesis, Cytostatic and Antibacterial Evaluations of Novel 1,2,3-Triazolyl-tagged Pyrimidine and Furo[2,3-d]pyrimidine Derivatives", Croatica Chemica Acta, vol.90, br. 2, str. 197-205, 2017. [Online]. https://doi.org/10.5562/cca3165

Sažetak
C-5 alkynylated and N-1 alkylated pyrimidine derivatives were synthesized by N-alkylation reaction of 5-iodouracil in the presence of NaH, as a base, followed by Pd-catalyzed Sonogashira cross-coupling reaction of N-alkyl-5-iodouracil derivatives (1 and 2) with corresponding terminal alkynes. Intramolecular in situ O-heteroannulation ring closure of N-1-alkyl-C-5-alkynylpyrimidine derivatives (3 and 5) generated novel 6-substituted furo[2,3-d]pyrimidine derivatives (7 and 8). 1,4-Disubstituted 1,2,3-triazole tethered 5-alkynylpyrimidines (14–19) and 6-substituted furo[2,3-d]pyrimidines (20–22) were successfully prepared by the copper(I)-catalyzed click reaction of 5-iodo-N-1-propargylpyrimidine (2) using microwave irradiation, followed by Sonogashira cross-coupling reaction with corresponding terminal alkynes. In vitro antiproliferative activity of prepared compounds evaluated on human cancer cell lines cervix adenocarcinoma (HeLa), colon adenocarcinoma (CaCo-2), chronic myeloid leukemia in blast crisis (K562), Burkitt lymphoma (Raji) revealed that pyrimidine (19) and furo[2,3-d]pyrimidine (22) derivatives with 3,5-difluorophenyl at pyrimidine and furo[2,3-d]pyrimidine as well as p-(trifluoromethyl)phenyl at 1,2,3-triazole exhibited marked and selective inhibitory effects on the growth of K562 and Raji tumor cells. Antibacterial evaluations showed that pyrimidine derivative 14 substituted with p-tolylethynyl at C-5 of pyrimidine and benzyl at 1,2,3-triazole moiety was the most active of all evaluated compounds on the Gram positive bacterial strains Enterococcus faecalis. Further structure optimization of compounds 14, 19 and 22 is foreseen in order to obtain lead structural analogs with efficient and selective antitumoral and antibacterial activities.

Creative Commons License This work is licensed under a Creative Commons Attribution 4.0 International License.

Ključne riječi
pyrimidine; furo[2; 3-d]pyrimidine; Sonogashira cross-coupling reaction; click chemistry; antiproliferative; antibacterial evaluations

Hrčak ID: 185003

URI
https://hrcak.srce.hr/185003

Posjeta: 1.119 *