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Pregled bibliografske jedinice broj: 1123754

6-Morpholino- and 6-amino-9-sulfonylpurine derivatives. Synthesis, computational analysis, and biological activity


Matić, Josipa; Jukić, Marijana; Ismaili, Hamit; Saftić, Dijana; Ban, Željka; Tandarić, Tana; Vianello, Robert; Opačak-Bernardi, Teuta; Glavaš-Obrovac, Ljubica; Žinić, Biserka
6-Morpholino- and 6-amino-9-sulfonylpurine derivatives. Synthesis, computational analysis, and biological activity // Nucleosides, nucleotides & nucleic acids, 40 (2021), 4; 470-503 doi:10.1080/15257770.2021.1896001 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1123754 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
6-Morpholino- and 6-amino-9-sulfonylpurine derivatives. Synthesis, computational analysis, and biological activity

Autori
Matić, Josipa ; Jukić, Marijana ; Ismaili, Hamit ; Saftić, Dijana ; Ban, Željka ; Tandarić, Tana ; Vianello, Robert ; Opačak-Bernardi, Teuta ; Glavaš-Obrovac, Ljubica ; Žinić, Biserka

Izvornik
Nucleosides, nucleotides & nucleic acids (1525-7770) 40 (2021), 4; 470-503

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

Ključne riječi
6-Chloropurine ; 6- morpholinopurine ; adenine ; regioselective N-9- sulfonylation ; DFT calculations ; biological activity

Sažetak
The synthesis of novel 6- chloro/morpholino/amino/-9-sulfonylpurine derivatives was accomplished in two ways, either (i) involving the condensation reaction of 6- chloropurine with commercially available arylsulfonyl chlorides in acetone and the presence of aqueous KOH at 0 °C, followed by the substitution of C6-chlorine with morpholine, or (ii) employing a reversed synthetic approach where 6-morpholinopurine and commercially available adenine bases were reacted with the corresponding alkyl, 2-arylethene and arylsulfonyl chlorides giving the N9 sulfonylated products, the latter particularly used where prior nonselective sulfonylation was observed. In both approaches, the sulfonylation reaction occurred regioselectively at the purine N9 position lacking any concurrent N7 derivatives, except in the case of a smaller methyl substituent on SO2 and the free amino group at C6 of the purine ring. The tautomeric features of initial N9 unsubstituted purines, as well as stability trends among the prepared N-9-sulfonylpurine derivates, were investigated using DFT calculations with an important conclusion that electron-donating C6 substituents are beneficial for the synthesis as they both promote the predominance of the desired N9 tautomers and help to assure the stability of the final products. The newly synthesized 6- morpholino and 6-amino-9-sulfonylpurine derivatives showed antiproliferative activity on human carcinoma, lymphoma, and leukemia cells. Among the tested compounds, 6-morpholino 17 and 6- amino 22 derivatives, with trans-β-styrenesulfonyl group attached at the N9 position of purine, proved to be the most effective antiproliferative agents, causing accumulation of leukemia cells in subG0 cell cycle phase.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
MZOS-098-0982914-2935 - Sinteza novih biološki aktivnih derivata nukleobaza i nukleotida (Žinić, Biserka, MZOS ) ( POIROT)
HRZZ-IP-2013-11-1477 - Višenamjensko očitavanje DNA/RNA sekundarne strukture molekularnim kemijskim senzorima (DNA/RNA-MolSense) (Piantanida, Ivo, HRZZ - 2013-11) ( POIROT)

Ustanove:
Institut "Ruđer Bošković", Zagreb,
Medicinski fakultet, Osijek

Poveznice na cjeloviti tekst rada:

doi www.tandfonline.com doi.org

Citiraj ovu publikaciju:

Matić, Josipa; Jukić, Marijana; Ismaili, Hamit; Saftić, Dijana; Ban, Željka; Tandarić, Tana; Vianello, Robert; Opačak-Bernardi, Teuta; Glavaš-Obrovac, Ljubica; Žinić, Biserka
6-Morpholino- and 6-amino-9-sulfonylpurine derivatives. Synthesis, computational analysis, and biological activity // Nucleosides, nucleotides & nucleic acids, 40 (2021), 4; 470-503 doi:10.1080/15257770.2021.1896001 (međunarodna recenzija, članak, znanstveni)
Matić, J., Jukić, M., Ismaili, H., Saftić, D., Ban, Ž., Tandarić, T., Vianello, R., Opačak-Bernardi, T., Glavaš-Obrovac, L. & Žinić, B. (2021) 6-Morpholino- and 6-amino-9-sulfonylpurine derivatives. Synthesis, computational analysis, and biological activity. Nucleosides, nucleotides & nucleic acids, 40 (4), 470-503 doi:10.1080/15257770.2021.1896001.
@article{article, author = {Mati\'{c}, Josipa and Juki\'{c}, Marijana and Ismaili, Hamit and Safti\'{c}, Dijana and Ban, \v{Z}eljka and Tandari\'{c}, Tana and Vianello, Robert and Opa\v{c}ak-Bernardi, Teuta and Glava\v{s}-Obrovac, Ljubica and \v{Z}ini\'{c}, Biserka}, year = {2021}, pages = {470-503}, DOI = {10.1080/15257770.2021.1896001}, keywords = {6-Chloropurine, 6- morpholinopurine, adenine, regioselective N-9- sulfonylation, DFT calculations, biological activity}, journal = {Nucleosides, nucleotides and nucleic acids}, doi = {10.1080/15257770.2021.1896001}, volume = {40}, number = {4}, issn = {1525-7770}, title = {6-Morpholino- and 6-amino-9-sulfonylpurine derivatives. Synthesis, computational analysis, and biological activity}, keyword = {6-Chloropurine, 6- morpholinopurine, adenine, regioselective N-9- sulfonylation, DFT calculations, biological activity} }
@article{article, author = {Mati\'{c}, Josipa and Juki\'{c}, Marijana and Ismaili, Hamit and Safti\'{c}, Dijana and Ban, \v{Z}eljka and Tandari\'{c}, Tana and Vianello, Robert and Opa\v{c}ak-Bernardi, Teuta and Glava\v{s}-Obrovac, Ljubica and \v{Z}ini\'{c}, Biserka}, year = {2021}, pages = {470-503}, DOI = {10.1080/15257770.2021.1896001}, keywords = {6-Chloropurine, 6- morpholinopurine, adenine, regioselective N-9- sulfonylation, DFT calculations, biological activity}, journal = {Nucleosides, nucleotides and nucleic acids}, doi = {10.1080/15257770.2021.1896001}, volume = {40}, number = {4}, issn = {1525-7770}, title = {6-Morpholino- and 6-amino-9-sulfonylpurine derivatives. Synthesis, computational analysis, and biological activity}, keyword = {6-Chloropurine, 6- morpholinopurine, adenine, regioselective N-9- sulfonylation, DFT calculations, biological activity} }

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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