Synthesis, X-ray crystal structure, anticancer activity, DFT, and molecular docking studies of 1,2,4-triazole linked indolyl thioglycosides.
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| Title: | Synthesis, X-ray crystal structure, anticancer activity, DFT, and molecular docking studies of 1,2,4-triazole linked indolyl thioglycosides. |
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| Authors: | Chauhan, Deepanshi1 (AUTHOR), Kumar, Ravendra1 (AUTHOR), Gupta, Rakesh Kumar2 (AUTHOR), Pratap, Rajesh3 (AUTHOR), Dubey, Pawan K.2 (AUTHOR), Kushwaha, Divya1 (AUTHOR) divyakush.mmvbhu@ac.in |
| Source: | Journal of Molecular Structure. Feb2026:Part 2, Vol. 1351, pN.PAG-N.PAG. 1p. |
| Subjects: | X-ray crystallography, Antineoplastic agents, Molecular docking, Triazole derivatives, Density functional theory, Chemical synthesis |
| Abstract: | • Efficient synthesis and structural characterization of 1,2,4-triazole-linked indole thioglycosides (9a – c). • X-ray crystallographic analysis revealed complex intermolecular (sp³/sp²) C–H...π interactions and hydrogen-bonding networks involving (sp³/sp²) C–H...N/O and N–H...N contacts. • DFT studies (HOMO–LUMO, MEP, NBO, and dual descriptor analyses) provided insights into electronic structure, chemical reactivity, and possible drug–receptor interactions. • Anticancer potential against MCF-7 breast cancer cells, further supported by molecular docking and ADMET predictions. In this study, a series of 1,2,4-triazole-linked indole thioglycosides (9a – c) was synthesized via nucleophilic substitution of 5-(1 H -indol-2-yl)-4-phenyl-2,4-dihydro-3 H -1,2,4-triazole-3-thione (5) with glycosyl bromides (8a – c). The structure of the compounds was elucidated using spectroscopic techniques, including NMR, IR, and HRMS. The molecular structures of compounds 9a and 9b were further confirmed by single-crystal X-ray diffraction. The configurations of the glycosidic and heterocyclic moieties were examined through analysis of the planarity of key structural fragments and the dihedral angles between them. The anticancer potential of the compounds was evaluated in vitro against the MCF-7 human breast cancer cell line, where compounds demonstrated moderate to poor cytotoxic activity. Molecular docking studies revealed strong binding affinities of the synthesized compounds toward the CDK2 enzyme (−9.1 to −9.2 kcal/mol), comparable to that of the reference inhibitor roscovitine. Additionally, DFT calculations were performed to evaluate key electronic and chemical parameters such as HOMO–LUMO energies, reactivity, stability, electronegativity, chemical potential, electrophilicity, and electronic charge distribution. These insights provide a deeper understanding of the compounds' chemical behaviour and can aid in predicting their reactivity and interactions, particularly in the context of drug–receptor binding. [Display omitted] [ABSTRACT FROM AUTHOR] |
| Copyright of Journal of Molecular Structure is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | Engineering Source |
| FullText | Text: Availability: 0 |
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| Header | DbId: egs DbLabel: Engineering Source An: 189385921 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Synthesis, X-ray crystal structure, anticancer activity, DFT, and molecular docking studies of 1,2,4-triazole linked indolyl thioglycosides. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Chauhan%2C+Deepanshi%22">Chauhan, Deepanshi</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Kumar%2C+Ravendra%22">Kumar, Ravendra</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Gupta%2C+Rakesh+Kumar%22">Gupta, Rakesh Kumar</searchLink><relatesTo>2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Pratap%2C+Rajesh%22">Pratap, Rajesh</searchLink><relatesTo>3</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Dubey%2C+Pawan+K%2E%22">Dubey, Pawan K.</searchLink><relatesTo>2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Kushwaha%2C+Divya%22">Kushwaha, Divya</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> divyakush.mmvbhu@ac.in</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Molecular+Structure%22">Journal of Molecular Structure</searchLink>. Feb2026:Part 2, Vol. 1351, pN.PAG-N.PAG. 1p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22X-ray+crystallography%22">X-ray crystallography</searchLink><br /><searchLink fieldCode="DE" term="%22Antineoplastic+agents%22">Antineoplastic agents</searchLink><br /><searchLink fieldCode="DE" term="%22Molecular+docking%22">Molecular docking</searchLink><br /><searchLink fieldCode="DE" term="%22Triazole+derivatives%22">Triazole derivatives</searchLink><br /><searchLink fieldCode="DE" term="%22Density+functional+theory%22">Density functional theory</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+synthesis%22">Chemical synthesis</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: • Efficient synthesis and structural characterization of 1,2,4-triazole-linked indole thioglycosides (9a – c). • X-ray crystallographic analysis revealed complex intermolecular (sp³/sp²) C–H...π interactions and hydrogen-bonding networks involving (sp³/sp²) C–H...N/O and N–H...N contacts. • DFT studies (HOMO–LUMO, MEP, NBO, and dual descriptor analyses) provided insights into electronic structure, chemical reactivity, and possible drug–receptor interactions. • Anticancer potential against MCF-7 breast cancer cells, further supported by molecular docking and ADMET predictions. In this study, a series of 1,2,4-triazole-linked indole thioglycosides (9a – c) was synthesized via nucleophilic substitution of 5-(1 H -indol-2-yl)-4-phenyl-2,4-dihydro-3 H -1,2,4-triazole-3-thione (5) with glycosyl bromides (8a – c). The structure of the compounds was elucidated using spectroscopic techniques, including NMR, IR, and HRMS. The molecular structures of compounds 9a and 9b were further confirmed by single-crystal X-ray diffraction. The configurations of the glycosidic and heterocyclic moieties were examined through analysis of the planarity of key structural fragments and the dihedral angles between them. The anticancer potential of the compounds was evaluated in vitro against the MCF-7 human breast cancer cell line, where compounds demonstrated moderate to poor cytotoxic activity. Molecular docking studies revealed strong binding affinities of the synthesized compounds toward the CDK2 enzyme (−9.1 to −9.2 kcal/mol), comparable to that of the reference inhibitor roscovitine. Additionally, DFT calculations were performed to evaluate key electronic and chemical parameters such as HOMO–LUMO energies, reactivity, stability, electronegativity, chemical potential, electrophilicity, and electronic charge distribution. These insights provide a deeper understanding of the compounds' chemical behaviour and can aid in predicting their reactivity and interactions, particularly in the context of drug–receptor binding. [Display omitted] [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Journal of Molecular Structure is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1016/j.molstruc.2025.144243 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 1 StartPage: N.PAG Subjects: – SubjectFull: X-ray crystallography Type: general – SubjectFull: Antineoplastic agents Type: general – SubjectFull: Molecular docking Type: general – SubjectFull: Triazole derivatives Type: general – SubjectFull: Density functional theory Type: general – SubjectFull: Chemical synthesis Type: general Titles: – TitleFull: Synthesis, X-ray crystal structure, anticancer activity, DFT, and molecular docking studies of 1,2,4-triazole linked indolyl thioglycosides. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Chauhan, Deepanshi – PersonEntity: Name: NameFull: Kumar, Ravendra – PersonEntity: Name: NameFull: Gupta, Rakesh Kumar – PersonEntity: Name: NameFull: Pratap, Rajesh – PersonEntity: Name: NameFull: Dubey, Pawan K. – PersonEntity: Name: NameFull: Kushwaha, Divya IsPartOfRelationships: – BibEntity: Dates: – D: 05 M: 02 Text: Feb2026:Part 2 Type: published Y: 2026 Identifiers: – Type: issn-print Value: 00222860 Numbering: – Type: volume Value: 1351 Titles: – TitleFull: Journal of Molecular Structure Type: main |
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