LAPSE:2023.36161
Published Article
LAPSE:2023.36161
N-Substituted (Hexahydro)-1H-isoindole-1,3(2H)-dione Derivatives: New Insights into Synthesis and Characterization
July 4, 2023
Novel phthalimide derivatives, namely N-(1,3-dioxoisoindolin-2-yl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide (1a) and N-(1,3-dioxoisoindolin-2-yl)thiophene-2-carboxamide (1b), and hexahydrophthalimide derivative N-(1,3-dioxohexahydro-1H-isoindol-2(3H)-yl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide (2), have been synthesized. The phthalimide derivatives were synthesized from phthalic anhydride and 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetohydrazide or thiophene-2-carbohydrazide, and the hexahydrophthalimide derivative has been synthesized from hexahydrophthalic anhydride and 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetohydrazide. The chemical structures of the compounds are elucidated by Nuclear Magnetic Resonance (NMR) and Infrared (IR) spectra. The new in vitro antioxidant activities of the obtained substances were evaluated using the DPPH method. All tested compounds showed antioxidative activity, the most active compound being 1b. Bioinformatics tools were used for the prediction of pharmacokinetics and pharmacodynamics profiles. Our results showedthat all compounds have a suitable intestinal absorption rate, good BBB and CNS permeabilities and have as molecular targets MAO B, COX-2 and NF-KB, important for antioxidant activities.
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Keywords
anti-oxidant activity, hexahydrophthalimides, molecular docking, pharmacokinetics and pharmacodynamic profiles, phthalimides
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Suggested Citation
Bădiceanu CD, Mares C, Nuță DC, Avram S, Drăghici C, Udrea AM, Zarafu I, Chiriță C, Hovaneț MV, Limban C. N-Substituted (Hexahydro)-1H-isoindole-1,3(2H)-dione Derivatives: New Insights into Synthesis and Characterization. (2023). LAPSE:2023.36161
Author Affiliations
Bădiceanu CD: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 TraianVuia, 020956 Bucharest, Romania [ORCID]
Mares C: Department of Anatomy, Animal Physiology, and Biophysics, Faculty of Biology, University of Bucharest, 36-46 Bd. M. Kogalniceanu, 050107 Bucharest, Romania [ORCID]
Nuță DC: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 TraianVuia, 020956 Bucharest, Romania [ORCID]
Avram S: Department of Anatomy, Animal Physiology, and Biophysics, Faculty of Biology, University of Bucharest, 36-46 Bd. M. Kogalniceanu, 050107 Bucharest, Romania
Drăghici C: “C. D. Nenitzescu” Institute of Organic and Supramolecular Chemistry, 202B Splaiul Independentei, 060023 Bucharest, Romania
Udrea AM: Laser Department, National Institute for Laser, Plasma and Radiation Physics, Atomistilor 409, 077125 Magurele, Romania; Research Institute of the University of Bucharest—ICUB, University of Bucharest, 91-95 Splaiul Independentei, 050095 Bucharest, Roma [ORCID]
Zarafu I: Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, 4-12 Regina Elisabeta, 030018 Bucharest, Romania
Chiriță C: Department of Pharmacology and Clinical Pharmacy, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 TraianVuia, 020956 Bucharest, Romania
Hovaneț MV: Department of Pharmaceutical Botany and Cell Biology, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 TraianVuia, 020956 Bucharest, Romania
Limban C: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 TraianVuia, 020956 Bucharest, Romania
Mares C: Department of Anatomy, Animal Physiology, and Biophysics, Faculty of Biology, University of Bucharest, 36-46 Bd. M. Kogalniceanu, 050107 Bucharest, Romania [ORCID]
Nuță DC: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 TraianVuia, 020956 Bucharest, Romania [ORCID]
Avram S: Department of Anatomy, Animal Physiology, and Biophysics, Faculty of Biology, University of Bucharest, 36-46 Bd. M. Kogalniceanu, 050107 Bucharest, Romania
Drăghici C: “C. D. Nenitzescu” Institute of Organic and Supramolecular Chemistry, 202B Splaiul Independentei, 060023 Bucharest, Romania
Udrea AM: Laser Department, National Institute for Laser, Plasma and Radiation Physics, Atomistilor 409, 077125 Magurele, Romania; Research Institute of the University of Bucharest—ICUB, University of Bucharest, 91-95 Splaiul Independentei, 050095 Bucharest, Roma [ORCID]
Zarafu I: Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, 4-12 Regina Elisabeta, 030018 Bucharest, Romania
Chiriță C: Department of Pharmacology and Clinical Pharmacy, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 TraianVuia, 020956 Bucharest, Romania
Hovaneț MV: Department of Pharmaceutical Botany and Cell Biology, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 TraianVuia, 020956 Bucharest, Romania
Limban C: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 TraianVuia, 020956 Bucharest, Romania
Journal Name
Processes
Volume
11
Issue
6
First Page
1616
Year
2023
Publication Date
2023-05-25
Published Version
ISSN
2227-9717
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Original Submission
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PII: pr11061616, Publication Type: Journal Article
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LAPSE:2023.36161
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doi:10.3390/pr11061616
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[v1] (Original Submission)
Jul 4, 2023
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Jul 4, 2023
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https://psecommunity.org/LAPSE:2023.36161
Original Submitter
Calvin Tsay
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