Synthesis, structural characterization, DFT calculations and antiproliferative evaluation of novel spirohydantoin derivatives containing a substituted benzyl moiety
Two series of cycloalkanespiro-5-hydantoins, namely cyclohexanespiro-5-hydantoins and cycloheptanespiro-5-hydantoins with a 4-substituted benzyl or a 2-(4-substituted phenyl)-2-oxoethyl group at N3 position, were synthesized and their effects on proliferation of human colon (HCT-116), leukemia (K562...
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Published in | Journal of molecular structure Vol. 1180; pp. 48 - 62 |
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Main Authors | , , , , , , , , , |
Format | Journal Article |
Language | English |
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Elsevier B.V
15.03.2019
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Abstract | Two series of cycloalkanespiro-5-hydantoins, namely cyclohexanespiro-5-hydantoins and cycloheptanespiro-5-hydantoins with a 4-substituted benzyl or a 2-(4-substituted phenyl)-2-oxoethyl group at N3 position, were synthesized and their effects on proliferation of human colon (HCT-116), leukemia (K562) and breast (MDA-MB-231) cancer cell lines were tested. For comparison, we also described the 5,5-diphenylhydantoin analogues. The structural features of the investigated compounds were characterized by elemental analysis, FT-IR, UV–Vis, 1H and 13C NMR spectroscopy and X-ray crystallography. Regarding their structure–activity relationships, it was shown that the substitution on the benzyl moiety with the methoxy, chloro or bromo group potentiated the antiproliferative activity relative to the parent compounds, while an increase in the size of the cycloalkyl group resulted mostly in a decrease of the antiproliferative activity. The single crystal X-ray analysis revealed the existence of dimers and chains formed by the NH⋯O hydrogen bonds. The analysis of the molecular descriptors of Lipinski demonstrated that all investigated compounds obeyed the rule of five. To further understand their geometry and electronic structure, DFT calculations with B3LYP method using 6-311++G(d,p) basic set were performed. In this context, the UV–Vis spectra of the investigated compounds were analyzed in detail, whereby the predicted absorption spectra from DFT calculation matched the experimentally obtained ones, with a good correlation. The interesting physico-chemical and pharmacologically relevant properties of the investigated compounds warrant their further investigation.
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•In searching for new hydantoin-based drugs, two series of compounds were synthesized.•Compounds with the CH3O, Cl or Br group exhibited an improved antiproliferative activity.•Different modes of intermolecular aggregation in the crystal structures were identified.•Substituent effects were reflected in the geometries and electronic structures.•The investigated compounds were compatible with the Lipinski rule of five. |
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AbstractList | Two series of cycloalkanespiro-5-hydantoins, namely cyclohexanespiro-5-hydantoins and cycloheptanespiro-5-hydantoins with a 4-substituted benzyl or a 2-(4-substituted phenyl)-2-oxoethyl group at N3 position, were synthesized and their effects on proliferation of human colon (HCT-116), leukemia (K562) and breast (MDA-MB-231) cancer cell lines were tested. For comparison, we also described the 5,5-diphenylhydantoin analogues. The structural features of the investigated compounds were characterized by elemental analysis, FT-IR, UV–Vis, 1H and 13C NMR spectroscopy and X-ray crystallography. Regarding their structure–activity relationships, it was shown that the substitution on the benzyl moiety with the methoxy, chloro or bromo group potentiated the antiproliferative activity relative to the parent compounds, while an increase in the size of the cycloalkyl group resulted mostly in a decrease of the antiproliferative activity. The single crystal X-ray analysis revealed the existence of dimers and chains formed by the NH⋯O hydrogen bonds. The analysis of the molecular descriptors of Lipinski demonstrated that all investigated compounds obeyed the rule of five. To further understand their geometry and electronic structure, DFT calculations with B3LYP method using 6-311++G(d,p) basic set were performed. In this context, the UV–Vis spectra of the investigated compounds were analyzed in detail, whereby the predicted absorption spectra from DFT calculation matched the experimentally obtained ones, with a good correlation. The interesting physico-chemical and pharmacologically relevant properties of the investigated compounds warrant their further investigation.
[Display omitted]
•In searching for new hydantoin-based drugs, two series of compounds were synthesized.•Compounds with the CH3O, Cl or Br group exhibited an improved antiproliferative activity.•Different modes of intermolecular aggregation in the crystal structures were identified.•Substituent effects were reflected in the geometries and electronic structures.•The investigated compounds were compatible with the Lipinski rule of five. |
Author | Radovanović, Lidija D. Trišović, Nemanja P. Ušćumlić, Gordana S. Vitnik, Željko J. Valentić, Nataša V. Vitnik, Vesna D. Rogan, Jelena R. Božić Nedeljković, Biljana Đ. Lazić, Anita M. Božić, Bojan Đ. |
Author_xml | – sequence: 1 givenname: Anita M. surname: Lazić fullname: Lazić, Anita M. organization: Innovation Center, Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia – sequence: 2 givenname: Lidija D. surname: Radovanović fullname: Radovanović, Lidija D. organization: Innovation Center, Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia – sequence: 3 givenname: Bojan Đ. surname: Božić fullname: Božić, Bojan Đ. organization: Faculty of Biology, University of Belgrade, Belgrade, Serbia – sequence: 4 givenname: Biljana Đ. surname: Božić Nedeljković fullname: Božić Nedeljković, Biljana Đ. organization: Faculty of Biology, University of Belgrade, Belgrade, Serbia – sequence: 5 givenname: Vesna D. surname: Vitnik fullname: Vitnik, Vesna D. organization: Department of Chemistry, Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Belgrade, Serbia – sequence: 6 givenname: Željko J. orcidid: 0000-0003-0276-9238 surname: Vitnik fullname: Vitnik, Željko J. organization: Department of Chemistry, Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Belgrade, Serbia – sequence: 7 givenname: Jelena R. surname: Rogan fullname: Rogan, Jelena R. organization: Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia – sequence: 8 givenname: Nataša V. surname: Valentić fullname: Valentić, Nataša V. organization: Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia – sequence: 9 givenname: Gordana S. surname: Ušćumlić fullname: Ušćumlić, Gordana S. organization: Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia – sequence: 10 givenname: Nemanja P. surname: Trišović fullname: Trišović, Nemanja P. email: ntrisovic@tmf.bg.ac.rs organization: Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia |
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