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Pregled bibliografske jedinice broj: 1213446

Green solvent-free synthesis of new N-heterocycle-L-ascorbic acid hybrids and their antiproliferative evaluation


Bistrović Popov, Andrea, Meščić Macan, Andrijana; Jakopec, Silvio; Prpić, Helena; Harej Hrkać, Anja; Kraljević Pavelić, Sandra; Raić-Malić, Silvana
Green solvent-free synthesis of new N-heterocycle-L-ascorbic acid hybrids and their antiproliferative evaluation // Future Medicinal Chemistry, 14 (2022), 16; 1187-1202 doi:10.4155/fmc-2022-0047 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1213446 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Green solvent-free synthesis of new N-heterocycle-L-ascorbic acid hybrids and their antiproliferative evaluation

Autori
Bistrović Popov, Andrea, Meščić Macan, Andrijana ; Jakopec, Silvio ; Prpić, Helena ; Harej Hrkać, Anja ; Kraljević Pavelić, Sandra ; Raić-Malić, Silvana

Izvornik
Future Medicinal Chemistry (1756-8919) 14 (2022), 16; 1187-1202

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
1, 2, 3-triazole ; antitumor activity ; CuAAC, ; green chemistry ; L-ascorbic acid ; mechanochemistry ; nucleobase ; purine ; pyrimidine

Sažetak
Aim: The authors’ aim was to improve the application of copper-catalyzed azide-alkyne cycloaddition in the synthesis of hybrids containing biologically significant nucleobases and L-ascorbic acid scaffolds by introducing an environmentally friendly and waste- free ball mill. Results: Two series of hybrids with a purine, pyrrolo[2, 3-d]pyrimidine or 5- substituted pyrimidine attached to 2, 3-dibenzyl-L- ascorbic acid via a hydroxyethyl- (15a–23a) or ethylidene- 1, 2, 3-triazolyl (15b–23b) bridge were prepared by ball milling and conventional synthesis. The unsaturated 6-chloroadenine L-ascorbic acid derivative 16b can be highlighted as a lead compound and showed strong antiproliferative activity against HepG2 (hepatocellular carcinoma) and SW620 (colorectal adenocarcinoma) cells. Conclusion: Mechanochemical synthesis was superior in terms of sustainability, reaction rate and yield, highlighting the advantageous applications of ball milling over classical reactions.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
HRZZ-IP-2018-01-4682 - Novi spojevi temeljeni na bioizosterima purina za ispitivanje njihovih antitumorskih i antipatogenih djelovanja (PurBioCaPa) (Raić-Malić, Silvana, HRZZ - 2018-01) ( CroRIS)

Ustanove:
Fakultet kemijskog inženjerstva i tehnologije, Zagreb,
Sveučilište u Rijeci - Odjel za biotehnologiju

Poveznice na cjeloviti tekst rada:

doi dx.doi.org

Citiraj ovu publikaciju:

Bistrović Popov, Andrea, Meščić Macan, Andrijana; Jakopec, Silvio; Prpić, Helena; Harej Hrkać, Anja; Kraljević Pavelić, Sandra; Raić-Malić, Silvana
Green solvent-free synthesis of new N-heterocycle-L-ascorbic acid hybrids and their antiproliferative evaluation // Future Medicinal Chemistry, 14 (2022), 16; 1187-1202 doi:10.4155/fmc-2022-0047 (međunarodna recenzija, članak, znanstveni)
Bistrović Popov, Andrea, Meščić Macan, Andrijana, Jakopec, S., Prpić, H., Harej Hrkać, A., Kraljević Pavelić, S. & Raić-Malić, S. (2022) Green solvent-free synthesis of new N-heterocycle-L-ascorbic acid hybrids and their antiproliferative evaluation. Future Medicinal Chemistry, 14 (16), 1187-1202 doi:10.4155/fmc-2022-0047.
@article{article, author = {Jakopec, Silvio and Prpi\'{c}, Helena and Harej Hrka\'{c}, Anja and Kraljevi\'{c} Paveli\'{c}, Sandra and Rai\'{c}-Mali\'{c}, Silvana}, year = {2022}, pages = {1187-1202}, DOI = {10.4155/fmc-2022-0047}, keywords = {1, 2, 3-triazole, antitumor activity, CuAAC,, green chemistry, L-ascorbic acid, mechanochemistry, nucleobase, purine, pyrimidine}, journal = {Future Medicinal Chemistry}, doi = {10.4155/fmc-2022-0047}, volume = {14}, number = {16}, issn = {1756-8919}, title = {Green solvent-free synthesis of new N-heterocycle-L-ascorbic acid hybrids and their antiproliferative evaluation}, keyword = {1, 2, 3-triazole, antitumor activity, CuAAC,, green chemistry, L-ascorbic acid, mechanochemistry, nucleobase, purine, pyrimidine} }
@article{article, author = {Jakopec, Silvio and Prpi\'{c}, Helena and Harej Hrka\'{c}, Anja and Kraljevi\'{c} Paveli\'{c}, Sandra and Rai\'{c}-Mali\'{c}, Silvana}, year = {2022}, pages = {1187-1202}, DOI = {10.4155/fmc-2022-0047}, keywords = {1, 2, 3-triazole, antitumor activity, CuAAC,, green chemistry, L-ascorbic acid, mechanochemistry, nucleobase, purine, pyrimidine}, journal = {Future Medicinal Chemistry}, doi = {10.4155/fmc-2022-0047}, volume = {14}, number = {16}, issn = {1756-8919}, title = {Green solvent-free synthesis of new N-heterocycle-L-ascorbic acid hybrids and their antiproliferative evaluation}, keyword = {1, 2, 3-triazole, antitumor activity, CuAAC,, green chemistry, L-ascorbic acid, mechanochemistry, nucleobase, purine, pyrimidine} }

Časopis indeksira:


  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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