1,5-Benzodiazepin-2(3H)-ones: In Vitro Evaluation as Antiparkinsonian Agents
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A new series of twenty-three 1,5-benzodiazepin-2(3H)-ones were synthesized and evaluated in the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), ferric reducing antioxidant power (FRAP), and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assays as a new chemotype with antioxidant and good drug-like properties. All of the derivatives showed low cytotoxicity in comparison to curcumin against the human neuroblastoma SH-SY5Y and the human hepatoma HepG2 cell lines. Experimental solubility in bio-relevant media showed a good relationship with melting points in this series. Five compounds with the best antioxidant properties showed neuroprotectant activity against H2O2-induced oxidative stress in the SH-SY5Y cell line. From them, derivatives 4-phenyl-1H-1,5-benzodiazepin-2(3H)-one (18) and 4-(3,4,5-trimethoxyphenyl)-1H-1,5-benzodiazepin-2(3H)-one (20) yielded good neuroprotection activity in the same neuronal cell line under 6-OHD and MPP+ insults as in vitro models of mitochondrial dysfunction and oxidative stress in Parkinson’s disease (PD). Both compounds also demonstrated a significant reduction of intracellular Reactive Oxygen Species (ROS) and superoxide levels, in parallel with a good improvement of the Mitochondrial Membrane Potential (ΔΨm). Compared with curcumin, compound 18 better reduced lipid peroxidation levels, malondialdehyde (MDA), in SH-SY5Y cells under oxidative stress pressure and recovered intracellular glutathione synthetase (GSH) levels. Apoptosis and caspase-3 levels of SH-SY5Y under H2O2 pressure were also reduced after treatment with 18. Neuroprotection in neuron-like differentiated SH-SY5Y cells was also achieved with 18. In summary, this family of 1,5-benzodiazepin-2-ones with an interesting antioxidant and drug-like profile, with low cytotoxic and good neuroprotectant activity, constitutes a new promising chemical class with high potential for the development of new therapeutic agents against PD.
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Increasing GSH levels in the brain is a possible therapy for PD.
“Increasing GSH levels in the brain is a possible therapy for PD, and multiple experimental investigations have shown this strategy works [44,45].”
From Neuroprotective Effects of Bifidobacterium breve CCFM1067 in MPTP-Induced Mouse Models of Parkinson’s Disease (2022) · cites this paper as [45]
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- Authors
- Ortíz de Zárate, A., Pérez-Torralba, M., Bonet Isidro, I., López, C., Claramunt, R. M., Martínez-Casanova, D., Sánchez-Vera, I., Jiménez-González, J., & Lavandera, J. L.
- Affiliations
- Instituto de Medicina Molecular Aplicada (IMMA), Facultad de Medicina, Universidad San Pablo-CEU, CEU Universities, Campus de Montepríncipe, E-28668 Madrid, Spain
- Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, Universidad Nacional de Educación a Distancia (UNED), Paseo Senda del Rey 9, E-28040 Madrid, Spain
- Universidad Nacional de Educación a Distancia (ES)
- Universidad San Pablo CEU (ES)
- Corresponding author
- Claramunt, Rosa M.
- Venue
- Antioxidants
- Publisher
- MDPI AG
- Published
- 2021-10-09
- Volume
- 10
- Issue
- 10
- Pages
- 1584
- ISSN
- 2076-3921 (ISSN-L)
- PMC
- PMC8533176
- OpenAlex
- W3205468968
- Cited by
- 11
- References
- 182
- Citations by year
- 2026: 2 · 2025: 5 · 2024: 1 · 2023: 1 · 2022: 2
- FWCI
- 0.40
- Type
- journal article
- Language
- en
- Open access
- gold
- dx.doi.org
- Licence
- Locations
- Antioxidants (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- CEU Repositorio Institucional (Fundación Universitaria San Pablo CEU) (submittedVersion, cc-by-nc-nd)
- Funders
- Ministerio de Educación, Cultura y Deporte of Spain (PRX15/00567)
- Ministerio de Economía y Competitividad of Spain (CTQ2014-56833-R)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and pharmacology of benzodiazepine derivatives
- Health Sciences › Medicine › Neurology › Parkinson's Disease Mechanisms and Treatments
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and biological activity
- Keywords
- antiparkinsonian drugs, Parkinson's disease, neuroprotection, antioxidant activity, oxidative stress, mitochondrial dysfunction, reactive oxygen species, superoxide, mitochondrial membrane potential, lipid peroxidation, glutathione, caspase-3, apoptosis, SH-SY5Y cells, MPP+, 6-hydroxydopamine, curcumin
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
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