(2<i>R</i>, 4<i>S</i>, 5<i>S</i>) 1-(4-(4-(((7-Chloroquinolin-4-yl)amino)methyl)-1<i>H</i>-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione
1,2,3-triazole pharmacophore is a widely recognized motif used for a variety of applications, including drug discovery, chemical biology, and materials science. We herein report the synthesis of a derivative of azidothymidine (AZT), which was combined with the 7-chloro quinoline scaffold through a 1...
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| Format: | Article |
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MDPI AG
2023-07-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2023/3/M1681 |
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| author | Houin Kuan Yuhan Xie Yuzhu Guo Alessandra Gianoncelli Giovanni Ribaudo Paolo Coghi |
| author_facet | Houin Kuan Yuhan Xie Yuzhu Guo Alessandra Gianoncelli Giovanni Ribaudo Paolo Coghi |
| author_sort | Houin Kuan |
| collection | DOAJ |
| description | 1,2,3-triazole pharmacophore is a widely recognized motif used for a variety of applications, including drug discovery, chemical biology, and materials science. We herein report the synthesis of a derivative of azidothymidine (AZT), which was combined with the 7-chloro quinoline scaffold through a 1,4-disubstituted 1,2,3-triazole. The chemical structure of the new molecule was fully characterized by Fourier transform infrared (FTIR) spectroscopy, proton nuclear magnetic resonance (<sup>1</sup>H-NMR), carbon-13 nuclear magnetic resonance (<sup>13</sup>C-NMR), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC) distortionless enhancement by polarization transfer (DEPT), correlation spectroscopy (<sup>1</sup>H-<sup>1</sup>H-COSY), ultraviolet (UV) spectroscopy, and high-resolution mass spectrometry (HRMS). Computational studies were used to predict the interaction of the synthesized compound with HIV reverse transcriptase, a target of relevance for developing new therapeutics against AIDS. The drug-likeness of the compound was also investigated by computing the physico-chemical properties that are important for the pharmacokinetic profile. |
| first_indexed | 2024-03-10T22:26:14Z |
| format | Article |
| id | doaj.art-8a9c8e93df894623aca13b5ab19a8e67 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-10T22:26:14Z |
| publishDate | 2023-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-8a9c8e93df894623aca13b5ab19a8e672023-11-19T12:06:33ZengMDPI AGMolbank1422-85992023-07-0120233M168110.3390/M1681(2<i>R</i>, 4<i>S</i>, 5<i>S</i>) 1-(4-(4-(((7-Chloroquinolin-4-yl)amino)methyl)-1<i>H</i>-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dioneHouin Kuan0Yuhan Xie1Yuzhu Guo2Alessandra Gianoncelli3Giovanni Ribaudo4Paolo Coghi5School of Pharmacy, Macau University of Science and Technology, Macau 999078, ChinaSchool of Pharmacy, Macau University of Science and Technology, Macau 999078, ChinaSchool of Pharmacy, Macau University of Science and Technology, Macau 999078, ChinaDepartment of Molecular and Translational Medicine, University of Brescia, 25213 Brescia, ItalyDepartment of Molecular and Translational Medicine, University of Brescia, 25213 Brescia, ItalySchool of Pharmacy, Macau University of Science and Technology, Macau 999078, China1,2,3-triazole pharmacophore is a widely recognized motif used for a variety of applications, including drug discovery, chemical biology, and materials science. We herein report the synthesis of a derivative of azidothymidine (AZT), which was combined with the 7-chloro quinoline scaffold through a 1,4-disubstituted 1,2,3-triazole. The chemical structure of the new molecule was fully characterized by Fourier transform infrared (FTIR) spectroscopy, proton nuclear magnetic resonance (<sup>1</sup>H-NMR), carbon-13 nuclear magnetic resonance (<sup>13</sup>C-NMR), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC) distortionless enhancement by polarization transfer (DEPT), correlation spectroscopy (<sup>1</sup>H-<sup>1</sup>H-COSY), ultraviolet (UV) spectroscopy, and high-resolution mass spectrometry (HRMS). Computational studies were used to predict the interaction of the synthesized compound with HIV reverse transcriptase, a target of relevance for developing new therapeutics against AIDS. The drug-likeness of the compound was also investigated by computing the physico-chemical properties that are important for the pharmacokinetic profile.https://www.mdpi.com/1422-8599/2023/3/M1681HIV1,2,3-triazoledrug discoverymolecular docking |
| spellingShingle | Houin Kuan Yuhan Xie Yuzhu Guo Alessandra Gianoncelli Giovanni Ribaudo Paolo Coghi (2<i>R</i>, 4<i>S</i>, 5<i>S</i>) 1-(4-(4-(((7-Chloroquinolin-4-yl)amino)methyl)-1<i>H</i>-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione Molbank HIV 1,2,3-triazole drug discovery molecular docking |
| title | (2<i>R</i>, 4<i>S</i>, 5<i>S</i>) 1-(4-(4-(((7-Chloroquinolin-4-yl)amino)methyl)-1<i>H</i>-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione |
| title_full | (2<i>R</i>, 4<i>S</i>, 5<i>S</i>) 1-(4-(4-(((7-Chloroquinolin-4-yl)amino)methyl)-1<i>H</i>-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione |
| title_fullStr | (2<i>R</i>, 4<i>S</i>, 5<i>S</i>) 1-(4-(4-(((7-Chloroquinolin-4-yl)amino)methyl)-1<i>H</i>-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione |
| title_full_unstemmed | (2<i>R</i>, 4<i>S</i>, 5<i>S</i>) 1-(4-(4-(((7-Chloroquinolin-4-yl)amino)methyl)-1<i>H</i>-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione |
| title_short | (2<i>R</i>, 4<i>S</i>, 5<i>S</i>) 1-(4-(4-(((7-Chloroquinolin-4-yl)amino)methyl)-1<i>H</i>-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione |
| title_sort | 2 i r i 4 i s i 5 i s i 1 4 4 7 chloroquinolin 4 yl amino methyl 1 i h i 1 2 3 triazol 1 yl 5 hydroxymethyl tetrahydrofuran 2 yl 5 methylpyrimidine 2 4 1 i h i 3 i h i dione |
| topic | HIV 1,2,3-triazole drug discovery molecular docking |
| url | https://www.mdpi.com/1422-8599/2023/3/M1681 |
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