Synthesis of some mono- and disaccharide-grafting phthalazine derivatives and some new Se-nucleoside analogues: antibacterial properties, quantum chemical calculations, and cytotoxicity
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389013%3A_____%2F23%3A00566960" target="_blank" >RIV/61389013:_____/23:00566960 - isvavai.cz</a>
Result on the web
<a href="https://www.mdpi.com/1420-3049/28/1/317" target="_blank" >https://www.mdpi.com/1420-3049/28/1/317</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3390/molecules28010317" target="_blank" >10.3390/molecules28010317</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis of some mono- and disaccharide-grafting phthalazine derivatives and some new Se-nucleoside analogues: antibacterial properties, quantum chemical calculations, and cytotoxicity
Original language description
A highly efficient and versatile synthetic approach for the synthesis of 4-(pyren-1-ylmethyl)-1-(d-glycosyloxy) phthalazine nucleosides 11a,b, 13, β-S-nucleosides 16, 18, 20, and acyclo C-nucleosides 23a,b, 24, 25 and 27a–f was described and fully characterized. Furthermore, a series of desired new nucleoside analogues containing Se of 4-(pyren-1-ylmethyl) phthalazine-1(2H)-selenone 28–33 were synthesized. The structures of all reported compounds were confirmed by IR, 1H-NMR, 13C-NMR, MS and elemental analysis. All compounds have been screened for their antibacterial and antifungal activities. Maximum activity was shown by 20 and 33a comparable to the standard drugs with lower toxicity. The cytotoxicity of the selected compound was measured and evaluated. The energy gap between the highest occupied molecular orbital and lowest unoccupied molecular orbital was calculated using theoretical computations to reflect the chemical reactivity and kinetic stability of the synthesized compounds. Using density functional theory (DFT), electronic parameters such as the highest occupied and lowest unoccupied molecular orbitals (HOMO and LUMO) and the molecular electrostatic potential (MEPS) were calculated. On the basis of different studied structures, these properties were computed in order to elucidate the chemical reactivity and the kinetic stability. Obviously, the band gap energy (Eg) of structures studied reveals that the lowest band gap obtained for the structure 16-a indicates that it has the highest chemical reactivity and lowest kinetic stability.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10404 - Polymer science
Result continuities
Project
—
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Molecules
ISSN
1420-3049
e-ISSN
1420-3049
Volume of the periodical
28
Issue of the periodical within the volume
1
Country of publishing house
CH - SWITZERLAND
Number of pages
19
Pages from-to
317
UT code for WoS article
000908942000001
EID of the result in the Scopus database
2-s2.0-85145699652