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  1. Article ; Online: Synthesis of Bioactive Aminomethylated 8-Hydroxyquinolines via the Modified Mannich Reaction.

    Csuvik, Oszkár / Szatmári, István

    International journal of molecular sciences

    2023  Volume 24, Issue 9

    Abstract: 8-hydroxyquinoline (oxine) is a widely known and frequently used chelating agent, and the pharmacological effects of the core molecule and its derivatives have been studied since the 19th century. There are several synthetic methods to modify this core. ... ...

    Abstract 8-hydroxyquinoline (oxine) is a widely known and frequently used chelating agent, and the pharmacological effects of the core molecule and its derivatives have been studied since the 19th century. There are several synthetic methods to modify this core. The Mannich reaction is one of the most easily implementable examples, which requires mild reaction conditions and simple chemical reagents. The three components of the Mannich reaction are a primary or secondary amine, an aldehyde and a compound having a hydrogen with pronounced activity. In the modified Mannich reaction, naphthol or a nitrogen-containing naphthol analogue (e.g., 8-hydroxyquinoline) is utilised as the active hydrogen provider compound, thus affording the formation of aminoalkylated products. The amine component can be ammonia and primary or secondary amines. The aldehyde component is highly variable, including aliphatic and aromatic aldehydes. Based on the pharmacological relevance of aminomethylated 8-hydroxyquinolines, this review summarises their syntheses via the modified Mannich reaction starting from 8-hydroxyquinoline, formaldehyde and various amines.
    MeSH term(s) Oxyquinoline/pharmacology ; Naphthols/chemistry ; Amines/chemistry ; Aldehydes/chemistry ; Hydrogen ; Mannich Bases/chemistry
    Chemical Substances Oxyquinoline (5UTX5635HP) ; Naphthols ; Amines ; Aldehydes ; Hydrogen (7YNJ3PO35Z) ; Mannich Bases
    Language English
    Publishing date 2023-04-26
    Publishing country Switzerland
    Document type Journal Article ; Review
    ZDB-ID 2019364-6
    ISSN 1422-0067 ; 1422-0067 ; 1661-6596
    ISSN (online) 1422-0067
    ISSN 1422-0067 ; 1661-6596
    DOI 10.3390/ijms24097915
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Tryptophanhydroxamic Acid-Stabilized Ultrasmall Gold Nanoclusters: Tuning the Selectivity for Metal Ion Sensing.

    Gombár, Gyöngyi / Ungor, Ditta / Szatmári, István / Juhász, Ádám / Csapó, Edit

    Nanomaterials (Basel, Switzerland)

    2024  Volume 14, Issue 5

    Abstract: Sub-nanometer-sized gold nanoclusters (Au NCs) were prepared via the spontaneous reduction of [ ... ...

    Abstract Sub-nanometer-sized gold nanoclusters (Au NCs) were prepared via the spontaneous reduction of [AuCl
    Language English
    Publishing date 2024-02-27
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2662255-5
    ISSN 2079-4991
    ISSN 2079-4991
    DOI 10.3390/nano14050434
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  3. Article ; Online: The Impact of C-3 Side Chain Modifications on Kynurenic Acid: A Behavioral Analysis of Its Analogs in the Motor Domain.

    Martos, Diána / Lőrinczi, Bálint / Szatmári, István / Vécsei, László / Tanaka, Masaru

    International journal of molecular sciences

    2024  Volume 25, Issue 6

    Abstract: The central nervous system (CNS) is the final frontier in drug delivery because of the blood-brain barrier (BBB), which poses significant barriers to the access of most drugs to their targets. Kynurenic acid (KYNA), a tryptophan (Trp) metabolite, plays ... ...

    Abstract The central nervous system (CNS) is the final frontier in drug delivery because of the blood-brain barrier (BBB), which poses significant barriers to the access of most drugs to their targets. Kynurenic acid (KYNA), a tryptophan (Trp) metabolite, plays an important role in behavioral functions, and abnormal KYNA levels have been observed in neuropsychiatric conditions. The current challenge lies in delivering KYNA to the CNS owing to its polar side chain. Recently, C-3 side chain-modified KYNA analogs have been shown to cross the BBB; however, it is unclear whether they retain the biological functions of the parent molecule. This study examined the impact of KYNA analogs, specifically, SZR-72, SZR-104, and the newly developed SZRG-21, on behavior. The analogs were administered intracerebroventricularly (i.c.v.), and their effects on the motor domain were compared with those of KYNA. Specifically, open-field (OF) and rotarod (RR) tests were employed to assess motor activity and skills. SZR-104 increased horizontal exploratory activity in the OF test at a dose of 0.04 μmol/4 μL, while SZR-72 decreased vertical activity at doses of 0.04 and 0.1 μmol/4 μL. In the RR test, however, neither KYNA nor its analogs showed any significant differences in motor skills at either dose. Side chain modification affects affective motor performance and exploratory behavior, as the results show for the first time. In this study, we showed that KYNA analogs alter emotional components such as motor-associated curiosity and emotions. Consequently, drug design necessitates the development of precise strategies to traverse the BBB while paying close attention to modifications in their effects on behavior.
    MeSH term(s) Kynurenic Acid ; Blood-Brain Barrier ; Drug Delivery Systems ; Neuroprotective Agents/chemistry ; Open Field Test
    Chemical Substances Kynurenic Acid (H030S2S85J) ; Neuroprotective Agents
    Language English
    Publishing date 2024-03-16
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2019364-6
    ISSN 1422-0067 ; 1422-0067 ; 1661-6596
    ISSN (online) 1422-0067
    ISSN 1422-0067 ; 1661-6596
    DOI 10.3390/ijms25063394
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  4. Article ; Online: Novel Eco-friendly, One-Pot Method for the Synthesis of Kynurenic Acid Ethyl Esters.

    Simon, Péter / Lőrinczi, Bálint / Hetényi, Anasztázia / Szatmári, István

    ACS omega

    2023  Volume 8, Issue 20, Page(s) 17966–17975

    Abstract: The synthesis of kynurenic acid derivatives with potential biological effect was investigated and optimized for one-batch, two-step microwave-assisted reactions. Utilizing both chemically and biologically representative non-, methyl-, methoxy-, and ... ...

    Abstract The synthesis of kynurenic acid derivatives with potential biological effect was investigated and optimized for one-batch, two-step microwave-assisted reactions. Utilizing both chemically and biologically representative non-, methyl-, methoxy-, and chlorosubstituted aniline derivatives, in catalyst-free conditions, syntheses of seven kynurenic acid derivatives were achieved in a time frame of 2-3.5 h. In place of halogenated reaction media, tuneable green solvents were introduced for each analogue. The potential of green solvent mixtures to replace traditional solvents and to alter the regioisomeric ratio regarding the Conrad-Limpach method was highlighted. The advantages of the fast, eco-friendly, inexpensive analytic technique of TLC densitometry were emphasized for reaction monitoring and conversion determination in comparison to quantitative NMR. Moreover, the developed 2-3.5 h syntheses were scaled-up to achieve gram-scale products of KYNA derivatives, without altering the reaction time in the halogenated solvent DCB and more importantly in its green substitutes.
    Language English
    Publishing date 2023-05-11
    Publishing country United States
    Document type Journal Article
    ISSN 2470-1343
    ISSN (online) 2470-1343
    DOI 10.1021/acsomega.3c01170
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: KYNA Derivatives with Modified Skeleton; Hydroxyquinolines with Potential Neuroprotective Effect.

    Lőrinczi, Bálint / Szatmári, István

    International journal of molecular sciences

    2021  Volume 22, Issue 21

    Abstract: Kynurenic acid (KYNA) is an endogenous neuroprotective agent of increasing importance. Several derivatives have already been synthesized, bearing an abundance of functional groups attached to the main skeleton in different positions. Several of these ... ...

    Abstract Kynurenic acid (KYNA) is an endogenous neuroprotective agent of increasing importance. Several derivatives have already been synthesized, bearing an abundance of functional groups attached to the main skeleton in different positions. Several of these compounds have already been tested in biological evaluations, with several of them targeting the same receptors and biological effects as KYNA. However, these modified compounds build upon the unmodified KYNA skeleton leaving a possible route for the synthesis of new, potentially neuroprotective derivatives with heteroatom-containing ring systems. The aim of this review is to summarize the syntheses of KYNA derivatives with altered skeletons and to pinpoint an appealing transformation for future medicinal lead molecules.
    MeSH term(s) Animals ; Humans ; Hydroxyquinolines/chemistry ; Kynurenic Acid/pharmacology ; Neurodegenerative Diseases/drug therapy ; Neurodegenerative Diseases/pathology ; Neuroprotective Agents/pharmacology
    Chemical Substances Hydroxyquinolines ; Neuroprotective Agents ; Kynurenic Acid (H030S2S85J)
    Language English
    Publishing date 2021-11-03
    Publishing country Switzerland
    Document type Journal Article ; Review
    ZDB-ID 2019364-6
    ISSN 1422-0067 ; 1422-0067 ; 1661-6596
    ISSN (online) 1422-0067
    ISSN 1422-0067 ; 1661-6596
    DOI 10.3390/ijms222111935
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  6. Article: Comparative transcriptomic analysis of Illumina and MGI next-generation sequencing platforms using RUNX3- and ZBTB46-instructed embryonic stem cells.

    Póliska, Szilárd / Fareh, Chahra / Lengyel, Adél / Göczi, Loránd / Tőzsér, József / Szatmari, Istvan

    Frontiers in genetics

    2024  Volume 14, Page(s) 1275383

    Abstract: Introduction: ...

    Abstract Introduction:
    Language English
    Publishing date 2024-01-05
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2606823-0
    ISSN 1664-8021
    ISSN 1664-8021
    DOI 10.3389/fgene.2023.1275383
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  7. Article ; Online: Cyclic Amines Coupled to Indole Derivatives With Improved Efflux Pump Inhibiting Activity in Bacteria and Cancer Cells.

    Hegedűs, Dóra / Szemerédi, Nikoletta / Gábor, Maja / Sas, Judit / Belasri, Khadija / Szatmári, István / Spengler, Gabriella

    Anticancer research

    2024  Volume 44, Issue 3, Page(s) 1149–1160

    Abstract: Background/aim: Indole skeleton has become a significant tool in the field of anticancer and antibacterial therapeutic strategies. The modified aza-Friedel-Crafts reaction by direct coupling of different cyclic imines and indole derivatives has been ... ...

    Abstract Background/aim: Indole skeleton has become a significant tool in the field of anticancer and antibacterial therapeutic strategies. The modified aza-Friedel-Crafts reaction by direct coupling of different cyclic imines and indole derivatives has been explored. To investigate the scope and limitations of the reaction and observe the effect of structural modifications, our aim was to resynthesize selected compounds as well as prepare new derivatives starting from 6,7-dimethoxy-3,4-dihydroisoquinoline, (4aR,8aR)-4a,5,6,7,8,8a-hexahydroquinoxalin-2(1H)-one and 7-azaindole. Our further aim was the systematic biological evaluation of selected C-3-coupled indole and azaindole derivatives in favour of having a preliminary overview about the structure-activity relationships.
    Materials and methods: The synthesis and resynthesis of selected compounds were accomplished by extension of aza-Friedel-Crafts reaction. The products have been tested on bacteria and cancer cells.
    Results: The most significant efflux pump inhibiting (EPI) activity was observed in the case of 6,7-dihydrothieno[3,2-c]pyridine coupled indole derivative. The reaction of 6,7-dimethoxy-3,4-dihydroisoquinoline with 7-azaindole resulted in the most potent biofilm inhibitor product. Applying indole and 4,9-dihydro-3H-β-carboline, 6,7-dihydrothieno[3,2-c]pyridine led to the formation of a product with the highest anticancer activity. 6,7-Dimethoxy-3,4-dihydroisoquinoline skeleton and indole as an electron-rich aromatic compound have been found to be effective in the inhibition of ABCB1.
    Conclusion: The compounds presented in the study were investigated regarding different aspects of antibacterial and anticancer activities. Accordingly, some compounds were found to have antibacterial effect on Escherichia coli and Staphylococcus aureus strains, certain C-3-coupled derivatives showed toxicity on sensitive and ABCB1 efflux pump expressing colon adenocarcinoma and a normal, non-cancerous fibroblast cell lines.
    MeSH term(s) Humans ; Adenocarcinoma ; Colonic Neoplasms ; Antipsychotic Agents ; Bacteria ; Adamantane ; Anti-Bacterial Agents/pharmacology ; Antiviral Agents ; Amines
    Chemical Substances Antipsychotic Agents ; Adamantane (PJY633525U) ; Anti-Bacterial Agents ; Antiviral Agents ; Amines
    Language English
    Publishing date 2024-02-29
    Publishing country Greece
    Document type Journal Article
    ZDB-ID 604549-2
    ISSN 1791-7530 ; 0250-7005
    ISSN (online) 1791-7530
    ISSN 0250-7005
    DOI 10.21873/anticanres.16910
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  8. Article ; Online: Fine-Tuned Reactivity of

    Csuvik, Oszkár / Barta, Petra / Csámpai, Antal / Szatmári, István

    International journal of molecular sciences

    2022  Volume 23, Issue 20

    Abstract: 6-Hydroxyquinoline and 3-hydroxyisoquinoline ... ...

    Abstract 6-Hydroxyquinoline and 3-hydroxyisoquinoline as
    MeSH term(s) Mannich Bases/chemistry ; Naphthols ; Methanol ; Water/chemistry ; Morpholines ; Aldehydes
    Chemical Substances Mannich Bases ; Naphthols ; Methanol (Y4S76JWI15) ; Water (059QF0KO0R) ; Morpholines ; Aldehydes
    Language English
    Publishing date 2022-10-15
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2019364-6
    ISSN 1422-0067 ; 1422-0067 ; 1661-6596
    ISSN (online) 1422-0067
    ISSN 1422-0067 ; 1661-6596
    DOI 10.3390/ijms232012329
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  9. Article ; Online: Synthesis of Indole-Coupled KYNA Derivatives via C-N Bond Cleavage of Mannich Bases.

    Lőrinczi, Bálint / Simon, Péter / Szatmári, István

    International journal of molecular sciences

    2022  Volume 23, Issue 13

    Abstract: KYNAs, a compound with endogenous neuroprotective functions and an indole that is a building block of many biologically active compounds, such as a variety of neurotransmitters, are reacted in a transformation building upon Mannich bases. The reaction ... ...

    Abstract KYNAs, a compound with endogenous neuroprotective functions and an indole that is a building block of many biologically active compounds, such as a variety of neurotransmitters, are reacted in a transformation building upon Mannich bases. The reaction yields triarylmethane derivatives containing two biologically potent skeletons, and it may contribute to the synthesis of new, specialised neuroprotective compounds. The synthesis has been investigated via two procedures and the results were compared to those of previous studies. A possible alternative reaction route through acid catalysis has been established.
    MeSH term(s) Catalysis ; Indoles ; Mannich Bases/chemistry
    Chemical Substances Indoles ; Mannich Bases
    Language English
    Publishing date 2022-06-28
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2019364-6
    ISSN 1422-0067 ; 1422-0067 ; 1661-6596
    ISSN (online) 1422-0067
    ISSN 1422-0067 ; 1661-6596
    DOI 10.3390/ijms23137152
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  10. Article ; Online: Synthesis of 4-Hydroxyquinolines as Potential Cytotoxic Agents.

    Csuvik, Oszkár / Szemerédi, Nikoletta / Spengler, Gabriella / Szatmári, István

    International journal of molecular sciences

    2022  Volume 23, Issue 17

    Abstract: The synthesis of alkyl 2-(4-hydroxyquinolin-2-yl) acetates and 1-phenyl-4-(phenylamino)pyridine-2,6( ... ...

    Abstract The synthesis of alkyl 2-(4-hydroxyquinolin-2-yl) acetates and 1-phenyl-4-(phenylamino)pyridine-2,6(1
    MeSH term(s) Adenocarcinoma ; Antineoplastic Agents/pharmacology ; Benzylidene Compounds ; Colonic Neoplasms ; Cytotoxins ; Doxorubicin/pharmacology ; Humans ; Hydroxyquinolines
    Chemical Substances Antineoplastic Agents ; Benzylidene Compounds ; Cytotoxins ; Hydroxyquinolines ; Doxorubicin (80168379AG) ; 4-hydroxyquinoline (M1O131WXFO)
    Language English
    Publishing date 2022-08-26
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2019364-6
    ISSN 1422-0067 ; 1422-0067 ; 1661-6596
    ISSN (online) 1422-0067
    ISSN 1422-0067 ; 1661-6596
    DOI 10.3390/ijms23179688
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