Three Multi-Components Reaction: Synthesis and X-Ray Single-Crystal of Hydroacridinone-Based Hydrazino-<i>S</i>-Triazine Derivative as a New Class of Urease Inhibitor
The one-pot fashion of three multi-component reaction provides the desired hydroacridinone-based hydrazino-<i>s</i>-triazine scaffold <b>4</b>. Compound <b>4</b> was crystallized in an orthorhombic crystal system and Pbca space group with a = 11.6271(2) Å...
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| Format: | Article |
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MDPI AG
2019-12-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/10/1/14 |
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| author | Assem Barakat Saied M. Soliman Ayman El-Faham M. Ali Abdullah Mohammed Al-Majid Sammer Yousuf M. Iqbal Choudhary |
| author_facet | Assem Barakat Saied M. Soliman Ayman El-Faham M. Ali Abdullah Mohammed Al-Majid Sammer Yousuf M. Iqbal Choudhary |
| author_sort | Assem Barakat |
| collection | DOAJ |
| description | The one-pot fashion of three multi-component reaction provides the desired hydroacridinone-based hydrazino-<i>s</i>-triazine scaffold <b>4</b>. Compound <b>4</b> was crystallized in an orthorhombic crystal system and Pbca space group with a = 11.6271(2) Å, b = 18.2018(4) Å, c = 32.4721(6) Å, and α = β = γ = 90° with one formula unit per asymmetric unit and eight molecules per unit cell. Additionally, structural features, Hirshfeld surfaces, and DFT studies were also investigated. Its packing in the crystal is controlled by H…H (63.4%), O…H (12.7%), Cl…H (7.2%), N…H (4.7%), and C…H (10.2%) contacts, where the O…H and Cl…H contacts were found the strongest. In vitro urease inhibition evaluation showed that the hydroacridinone-based hydrazino-<i>s</i>-triazine is more active (IC<sub>50</sub> = 17.9 ± 0.47 µM) than the standard acetohydroxamic acid (IC<sub>50</sub> = 20.3 ± 0.43 µM). |
| first_indexed | 2024-04-11T13:43:25Z |
| format | Article |
| id | doaj.art-d8456cefba65490a836c2b03f027511e |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-04-11T13:43:25Z |
| publishDate | 2019-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-d8456cefba65490a836c2b03f027511e2022-12-22T04:21:10ZengMDPI AGCrystals2073-43522019-12-011011410.3390/cryst10010014cryst10010014Three Multi-Components Reaction: Synthesis and X-Ray Single-Crystal of Hydroacridinone-Based Hydrazino-<i>S</i>-Triazine Derivative as a New Class of Urease InhibitorAssem Barakat0Saied M. Soliman1Ayman El-Faham2M. Ali3Abdullah Mohammed Al-Majid4Sammer Yousuf5M. Iqbal Choudhary6Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, EgyptDepartment of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi ArabiaH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, PakistanH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, PakistanThe one-pot fashion of three multi-component reaction provides the desired hydroacridinone-based hydrazino-<i>s</i>-triazine scaffold <b>4</b>. Compound <b>4</b> was crystallized in an orthorhombic crystal system and Pbca space group with a = 11.6271(2) Å, b = 18.2018(4) Å, c = 32.4721(6) Å, and α = β = γ = 90° with one formula unit per asymmetric unit and eight molecules per unit cell. Additionally, structural features, Hirshfeld surfaces, and DFT studies were also investigated. Its packing in the crystal is controlled by H…H (63.4%), O…H (12.7%), Cl…H (7.2%), N…H (4.7%), and C…H (10.2%) contacts, where the O…H and Cl…H contacts were found the strongest. In vitro urease inhibition evaluation showed that the hydroacridinone-based hydrazino-<i>s</i>-triazine is more active (IC<sub>50</sub> = 17.9 ± 0.47 µM) than the standard acetohydroxamic acid (IC<sub>50</sub> = 20.3 ± 0.43 µM).https://www.mdpi.com/2073-4352/10/1/14three-component reactionhydroacridinonehydrazino-<i>s</i>-triazineurease inhibitorsdfthirshfeld surfaces |
| spellingShingle | Assem Barakat Saied M. Soliman Ayman El-Faham M. Ali Abdullah Mohammed Al-Majid Sammer Yousuf M. Iqbal Choudhary Three Multi-Components Reaction: Synthesis and X-Ray Single-Crystal of Hydroacridinone-Based Hydrazino-<i>S</i>-Triazine Derivative as a New Class of Urease Inhibitor Crystals three-component reaction hydroacridinone hydrazino-<i>s</i>-triazine urease inhibitors dft hirshfeld surfaces |
| title | Three Multi-Components Reaction: Synthesis and X-Ray Single-Crystal of Hydroacridinone-Based Hydrazino-<i>S</i>-Triazine Derivative as a New Class of Urease Inhibitor |
| title_full | Three Multi-Components Reaction: Synthesis and X-Ray Single-Crystal of Hydroacridinone-Based Hydrazino-<i>S</i>-Triazine Derivative as a New Class of Urease Inhibitor |
| title_fullStr | Three Multi-Components Reaction: Synthesis and X-Ray Single-Crystal of Hydroacridinone-Based Hydrazino-<i>S</i>-Triazine Derivative as a New Class of Urease Inhibitor |
| title_full_unstemmed | Three Multi-Components Reaction: Synthesis and X-Ray Single-Crystal of Hydroacridinone-Based Hydrazino-<i>S</i>-Triazine Derivative as a New Class of Urease Inhibitor |
| title_short | Three Multi-Components Reaction: Synthesis and X-Ray Single-Crystal of Hydroacridinone-Based Hydrazino-<i>S</i>-Triazine Derivative as a New Class of Urease Inhibitor |
| title_sort | three multi components reaction synthesis and x ray single crystal of hydroacridinone based hydrazino i s i triazine derivative as a new class of urease inhibitor |
| topic | three-component reaction hydroacridinone hydrazino-<i>s</i>-triazine urease inhibitors dft hirshfeld surfaces |
| url | https://www.mdpi.com/2073-4352/10/1/14 |
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