Synthesis of Some Mono- and Disaccharide-Grafting Phthalazine Derivatives and Some New <i>Se</i>-Nucleoside Analogues: Antibacterial Properties, Quantum Chemical Calculations, and Cytotoxicity
A highly efficient and versatile synthetic approach for the synthesis of 4-(pyren-1-ylmethyl)-1-(<span style="font-variant: small-caps;">d</span>-glycosyloxy) phthalazine nucleosides <b>11a</b>,<b>b</b>, <b>13</b>, <i>β</i>-<i&...
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| Format: | Article |
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MDPI AG
2022-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/1/317 |
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| author | I. E. El-Shamy E. Hleli A. A. Alsheikh M. A. Yawer M. A. El-Hashash J. Dybal A. M. Abdel-Mohsen |
| author_facet | I. E. El-Shamy E. Hleli A. A. Alsheikh M. A. Yawer M. A. El-Hashash J. Dybal A. M. Abdel-Mohsen |
| author_sort | I. E. El-Shamy |
| collection | DOAJ |
| description | A highly efficient and versatile synthetic approach for the synthesis of 4-(pyren-1-ylmethyl)-1-(<span style="font-variant: small-caps;">d</span>-glycosyloxy) phthalazine nucleosides <b>11a</b>,<b>b</b>, <b>13</b>, <i>β</i>-<i>S-</i>nucleosides <b>16</b>, <b>18</b>, <b>20</b>, and acyclo <i>C-</i>nucleosides <b>23a</b>,<b>b</b>, <b>24</b>, <b>25</b> and <b>27a</b>–<b>f</b> was described and fully characterized. Furthermore, a series of desired new nucleoside analogues containing Se of 4-(pyren-1-ylmethyl) phthalazine-1(2<i>H</i>)-selenone <b>28</b>–<b>33</b> were synthesized. The structures of all reported compounds were confirmed by IR, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, MS and elemental analysis. All compounds have been screened for their antibacterial and antifungal activities. Maximum activity was shown by <b>20</b> and <b>33a</b> 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 <b>16</b>-<b>a</b> indicates that it has the highest chemical reactivity and lowest kinetic stability. |
| first_indexed | 2024-03-09T09:44:15Z |
| format | Article |
| id | doaj.art-f616bb41701546a685b7768e97041c5e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T09:44:15Z |
| publishDate | 2022-12-01 |
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| series | Molecules |
| spelling | doaj.art-f616bb41701546a685b7768e97041c5e2023-12-02T00:42:12ZengMDPI AGMolecules1420-30492022-12-0128131710.3390/molecules28010317Synthesis of Some Mono- and Disaccharide-Grafting Phthalazine Derivatives and Some New <i>Se</i>-Nucleoside Analogues: Antibacterial Properties, Quantum Chemical Calculations, and CytotoxicityI. E. El-Shamy0E. Hleli1A. A. Alsheikh2M. A. Yawer3M. A. El-Hashash4J. Dybal5A. M. Abdel-Mohsen6Chemistry Department, Faculty of Science, Fayoum University, Fayoum 63514, EgyptInstitute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovského nám. 2, 162 06 Prague, Czech RepublicDepartment of Chemical Engineering, Faculty of Chemical and Petroleum Engineering, Albaath University, Homs 12574, SyriaDepartment of Chemistry, Division of Science and Technology, University of Education Lahore, Lahore 32200, PakistanChemistry Department, Faculty of Science, Ain Shams University, Cairo 11566, EgyptInstitute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovského nám. 2, 162 06 Prague, Czech RepublicInstitute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovského nám. 2, 162 06 Prague, Czech RepublicA highly efficient and versatile synthetic approach for the synthesis of 4-(pyren-1-ylmethyl)-1-(<span style="font-variant: small-caps;">d</span>-glycosyloxy) phthalazine nucleosides <b>11a</b>,<b>b</b>, <b>13</b>, <i>β</i>-<i>S-</i>nucleosides <b>16</b>, <b>18</b>, <b>20</b>, and acyclo <i>C-</i>nucleosides <b>23a</b>,<b>b</b>, <b>24</b>, <b>25</b> and <b>27a</b>–<b>f</b> was described and fully characterized. Furthermore, a series of desired new nucleoside analogues containing Se of 4-(pyren-1-ylmethyl) phthalazine-1(2<i>H</i>)-selenone <b>28</b>–<b>33</b> were synthesized. The structures of all reported compounds were confirmed by IR, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, MS and elemental analysis. All compounds have been screened for their antibacterial and antifungal activities. Maximum activity was shown by <b>20</b> and <b>33a</b> 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 <b>16</b>-<b>a</b> indicates that it has the highest chemical reactivity and lowest kinetic stability.https://www.mdpi.com/1420-3049/28/1/317mono/disaccharidesnucleoside analogues<i>S-</i>nucleosidesantibacterialbiocompatibilityquantum calculations |
| spellingShingle | I. E. El-Shamy E. Hleli A. A. Alsheikh M. A. Yawer M. A. El-Hashash J. Dybal A. M. Abdel-Mohsen Synthesis of Some Mono- and Disaccharide-Grafting Phthalazine Derivatives and Some New <i>Se</i>-Nucleoside Analogues: Antibacterial Properties, Quantum Chemical Calculations, and Cytotoxicity Molecules mono/disaccharides nucleoside analogues <i>S-</i>nucleosides antibacterial biocompatibility quantum calculations |
| title | Synthesis of Some Mono- and Disaccharide-Grafting Phthalazine Derivatives and Some New <i>Se</i>-Nucleoside Analogues: Antibacterial Properties, Quantum Chemical Calculations, and Cytotoxicity |
| title_full | Synthesis of Some Mono- and Disaccharide-Grafting Phthalazine Derivatives and Some New <i>Se</i>-Nucleoside Analogues: Antibacterial Properties, Quantum Chemical Calculations, and Cytotoxicity |
| title_fullStr | Synthesis of Some Mono- and Disaccharide-Grafting Phthalazine Derivatives and Some New <i>Se</i>-Nucleoside Analogues: Antibacterial Properties, Quantum Chemical Calculations, and Cytotoxicity |
| title_full_unstemmed | Synthesis of Some Mono- and Disaccharide-Grafting Phthalazine Derivatives and Some New <i>Se</i>-Nucleoside Analogues: Antibacterial Properties, Quantum Chemical Calculations, and Cytotoxicity |
| title_short | Synthesis of Some Mono- and Disaccharide-Grafting Phthalazine Derivatives and Some New <i>Se</i>-Nucleoside Analogues: Antibacterial Properties, Quantum Chemical Calculations, and Cytotoxicity |
| title_sort | synthesis of some mono and disaccharide grafting phthalazine derivatives and some new i se i nucleoside analogues antibacterial properties quantum chemical calculations and cytotoxicity |
| topic | mono/disaccharides nucleoside analogues <i>S-</i>nucleosides antibacterial biocompatibility quantum calculations |
| url | https://www.mdpi.com/1420-3049/28/1/317 |
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