X-ray Structures and Computational Studies of Two Bioactive 2-(Adamantane-1-carbonyl)-<i>N</i>-substituted Hydrazine-1-carbothioamides
Two biologically active adamantane-linked hydrazine-1-carbothioamide derivatives, namely 2-(adamantane-1-carbonyl)-<i>N</i>-(<i>tert</i>-butyl)hydrazine-1-carbothioamide) <b>1</b> and 2-(adamantane-1-carbonyl)-<i>N</i>-cyclohexylhydrazine-1-carbothioam...
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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/1420-3049/27/23/8425 |
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| author | Lamya H. Al-Wahaibi Kowsalya Alagappan Olivier Blacque Ahmed A. B. Mohamed Hanan M. Hassan María Judith Percino Ali A. El-Emam Subbiah Thamotharan |
| author_facet | Lamya H. Al-Wahaibi Kowsalya Alagappan Olivier Blacque Ahmed A. B. Mohamed Hanan M. Hassan María Judith Percino Ali A. El-Emam Subbiah Thamotharan |
| author_sort | Lamya H. Al-Wahaibi |
| collection | DOAJ |
| description | Two biologically active adamantane-linked hydrazine-1-carbothioamide derivatives, namely 2-(adamantane-1-carbonyl)-<i>N</i>-(<i>tert</i>-butyl)hydrazine-1-carbothioamide) <b>1</b> and 2-(adamantane-1-carbonyl)-<i>N</i>-cyclohexylhydrazine-1-carbothioamide <b>2,</b> have been synthesized. X-ray analysis was conducted to study the effect of the <i>t</i>-butyl and cyclohexyl moieties on the intermolecular interactions and conformation of the molecules in the solid state. X-ray analysis reveals that compound <b>1</b> exhibits folded conformation, whereas compound <b>2</b> adopts extended conformation. The Hirshfeld surface analysis indicates that the contributions of the major intercontacts involved in the stabilization of the crystal structures do not change much as a result of the <i>t</i>-butyl and cyclohexyl moieties. However, the presence and absence of these contacts is revealed by the 2D-fingerprint plots. The CLP–Pixel method was used to identify the energetically significant molecular dimers. These dimers are stabilized by different types of intermolecular interactions such as N–H···S, N–H···O, C–H···S, C–H···O, H–H bonding and C–H···π interactions. The strength of these interactions was quantified by using the QTAIM approach. The results suggest that N–H···O interaction is found to be stronger among other interactions. The in vitro assay suggests that both compounds <b>1</b> and <b>2</b> exhibit urease inhibition potential, and these compounds also display moderate antiproliferative activities. Molecular docking analysis shows the key interaction between urease enzyme and title compounds. |
| first_indexed | 2024-03-09T17:39:42Z |
| format | Article |
| id | doaj.art-7780e2100c184eaeb6610cd5f9cb2464 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T17:39:42Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-7780e2100c184eaeb6610cd5f9cb24642023-11-24T11:42:02ZengMDPI AGMolecules1420-30492022-12-012723842510.3390/molecules27238425X-ray Structures and Computational Studies of Two Bioactive 2-(Adamantane-1-carbonyl)-<i>N</i>-substituted Hydrazine-1-carbothioamidesLamya H. Al-Wahaibi0Kowsalya Alagappan1Olivier Blacque2Ahmed A. B. Mohamed3Hanan M. Hassan4María Judith Percino5Ali A. El-Emam6Subbiah Thamotharan7Department of Chemistry, College of Sciences, Princess Nourah Bint Abdulrahman University, Riyadh 11671, Saudi ArabiaBiomolecular Crystallography Laboratory, Department of Bioinformatics, School of Chemical and Biotechnology, SASTRA Deemed University, Thanjavur 613 401, IndiaDepartment of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, SwitzerlandDepartment of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, EgyptDepartment of Pharmacology and Biochemistry, Faculty of Pharmacy, Delta University for Science and Technology, International Costal Road, Gamasa City, Mansoura 11152, EgyptUnidad de Polímeros y Electrónica Orgánica, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Val3-Ecocampus Valsequillo, Independencia O2 Sur 50, San Pedro Zacachimalpa, Puebla 72960, MexicoDepartment of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, EgyptBiomolecular Crystallography Laboratory, Department of Bioinformatics, School of Chemical and Biotechnology, SASTRA Deemed University, Thanjavur 613 401, IndiaTwo biologically active adamantane-linked hydrazine-1-carbothioamide derivatives, namely 2-(adamantane-1-carbonyl)-<i>N</i>-(<i>tert</i>-butyl)hydrazine-1-carbothioamide) <b>1</b> and 2-(adamantane-1-carbonyl)-<i>N</i>-cyclohexylhydrazine-1-carbothioamide <b>2,</b> have been synthesized. X-ray analysis was conducted to study the effect of the <i>t</i>-butyl and cyclohexyl moieties on the intermolecular interactions and conformation of the molecules in the solid state. X-ray analysis reveals that compound <b>1</b> exhibits folded conformation, whereas compound <b>2</b> adopts extended conformation. The Hirshfeld surface analysis indicates that the contributions of the major intercontacts involved in the stabilization of the crystal structures do not change much as a result of the <i>t</i>-butyl and cyclohexyl moieties. However, the presence and absence of these contacts is revealed by the 2D-fingerprint plots. The CLP–Pixel method was used to identify the energetically significant molecular dimers. These dimers are stabilized by different types of intermolecular interactions such as N–H···S, N–H···O, C–H···S, C–H···O, H–H bonding and C–H···π interactions. The strength of these interactions was quantified by using the QTAIM approach. The results suggest that N–H···O interaction is found to be stronger among other interactions. The in vitro assay suggests that both compounds <b>1</b> and <b>2</b> exhibit urease inhibition potential, and these compounds also display moderate antiproliferative activities. Molecular docking analysis shows the key interaction between urease enzyme and title compounds.https://www.mdpi.com/1420-3049/27/23/8425adamantanehydrazine-1-carbothioamideHirshfeld surfaceCLP–PixelQTAIMmolecular docking |
| spellingShingle | Lamya H. Al-Wahaibi Kowsalya Alagappan Olivier Blacque Ahmed A. B. Mohamed Hanan M. Hassan María Judith Percino Ali A. El-Emam Subbiah Thamotharan X-ray Structures and Computational Studies of Two Bioactive 2-(Adamantane-1-carbonyl)-<i>N</i>-substituted Hydrazine-1-carbothioamides Molecules adamantane hydrazine-1-carbothioamide Hirshfeld surface CLP–Pixel QTAIM molecular docking |
| title | X-ray Structures and Computational Studies of Two Bioactive 2-(Adamantane-1-carbonyl)-<i>N</i>-substituted Hydrazine-1-carbothioamides |
| title_full | X-ray Structures and Computational Studies of Two Bioactive 2-(Adamantane-1-carbonyl)-<i>N</i>-substituted Hydrazine-1-carbothioamides |
| title_fullStr | X-ray Structures and Computational Studies of Two Bioactive 2-(Adamantane-1-carbonyl)-<i>N</i>-substituted Hydrazine-1-carbothioamides |
| title_full_unstemmed | X-ray Structures and Computational Studies of Two Bioactive 2-(Adamantane-1-carbonyl)-<i>N</i>-substituted Hydrazine-1-carbothioamides |
| title_short | X-ray Structures and Computational Studies of Two Bioactive 2-(Adamantane-1-carbonyl)-<i>N</i>-substituted Hydrazine-1-carbothioamides |
| title_sort | x ray structures and computational studies of two bioactive 2 adamantane 1 carbonyl i n i substituted hydrazine 1 carbothioamides |
| topic | adamantane hydrazine-1-carbothioamide Hirshfeld surface CLP–Pixel QTAIM molecular docking |
| url | https://www.mdpi.com/1420-3049/27/23/8425 |
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