Bioresearch of New 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones

Szkatuła, Dominika; Krzyżak, Edward; Mogilski, Szczepan; Sapa, Jacek; Filipek, Barbara; Świątek, Piotr

doi:10.3390/molecules25245883

Cited by 3 publications

(13 citation statements)

References 15 publications

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“…Pyrrolo[3,4- c ]pyridine derivatives have not been introduced into medicine so far, however, as it results from the studies presented in the literature, they exhibit various pharmacological activities. Derivatives with analgesic and sedative properties are by far the largest group [ 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 40 , 42 ]. Their antidiabetic [ 8 , 9 , 10 ], antiviral [ 12 , 13 , 14 , 15 ], antimycobacterial [ 16 , 17 , 18 , 19 ], and anticancer [ 20 , 21 , 22 , 23 , 24 ] activities have also been described.…”

Section: Discussionmentioning

confidence: 99%

“…In 2020, Szkatuła et al [ 37 ] published a paper reporting the synthesis and pharmacological results of novel 1 H -pyrrolo[3,4- c ]pyridine-1,3(2 H )-dione derivatives with potential sedative and analgesic activity. The structures of new derivatives 33a – 33h are shown in Figure 27 [ 37 ].…”

Section: Biological Activity Of Pyrrolo[34- C ]Pyridine Derivativesmentioning

confidence: 99%

“…The mechanism and extent of blood-brain barrier crossing were not defined. However, the observed sedative effect may indicate good penetration of the compounds in question into the central nervous system, which has not been proven either [ 37 ]. As mentioned earlier, the authors also described the analgesic activity of the new derivatives.…”

Section: Biological Activity Of Pyrrolo[34- C ]Pyridine Derivativesmentioning

confidence: 99%

“…In addition, the pharmacological activity of the two imides 33b (ED 50 = 3.25 mg/kg and 33d (ED 50 = 3.67mg/kg) was comparable to that of morphine used as a second reference drug (ED 50 = 2.44 mg/kg). However, in the case of the hot-plate test, the analgesic effects observed for the tested structures did not reach statistical significance [ 37 ].…”

Section: Biological Activity Of Pyrrolo[34- C ]Pyridine Derivativesmentioning

confidence: 99%

“…Removal of the hydroxyl group weakens the pharmacological effect. Shortening of this linker to 2 or 1 carbon atom also causes a decrease in activity, whereas lengthening the linker to 4 carbon atoms (butyl derivatives) did not increase the potency [ 37 ].…”

Section: Biological Activity Of Pyrrolo[34- C ]Pyridine Derivativesmentioning

confidence: 99%

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An Overview of the Biological Activity of Pyrrolo[3,4-c]pyridine Derivatives

Wójcicka

Redzicka

2021

Pharmaceuticals

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Pyrrolo[3,4-c]pyridine is one of the six structural isomers of the bicyclic ring system containing a pyrrole moiety fused to a pyridine nucleus. The broad spectrum of pharmacological properties of pyrrolo[3,4-c]pyridine derivatives is the main reason for developing new compounds containing this scaffold. This review presents studies on the biological activity of pyrrolo[3,4-c]pyridines that have been reported in the scientific literature. Most of these derivatives have been studied as analgesic and sedative agents. Biological investigations have shown that pyrrolo[3,4-c]pyridines can be used to treat diseases of the nervous and immune systems. Their antidiabetic, antimycobacterial, antiviral, and antitumor activities also have been found.

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Section: Discussionmentioning

confidence: 99%

Section: Biological Activity Of Pyrrolo[34- C ]Pyridine Derivativesmentioning

confidence: 99%

Section: Biological Activity Of Pyrrolo[34- C ]Pyridine Derivativesmentioning

confidence: 99%

Section: Biological Activity Of Pyrrolo[34- C ]Pyridine Derivativesmentioning

confidence: 99%

Section: Biological Activity Of Pyrrolo[34- C ]Pyridine Derivativesmentioning

confidence: 99%

See 3 more Smart Citations

An Overview of the Biological Activity of Pyrrolo[3,4-c]pyridine Derivatives

Wójcicka

Redzicka

2021

Pharmaceuticals

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A New N-Substituted 1H-Isoindole-1,3(2H)-Dione Derivative—Synthesis, Structure and Affinity for Cyclooxygenase Based on In Vitro Studies and Molecular Docking

Szkatuła

Krzyżak

Stanowska

et al. 2021

IJMS

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Isoindoline-1,3-dione derivatives constitute an important group of medicinal substances. In this study, nine new 1H-isoindole-1,3(2H)-dione derivatives and five potential pharmacophores were obtained in good yield (47.24–92.91%). The structure of the new imides was confirmed by the methods of elemental and spectral analysis: FT–IR, H NMR, and MS. Based on the obtained results of ESI–MS the probable path of the molecules decay and the hypothetical structure of the resulting pseudo-molecular ions have been proposed. The physicochemical properties of the new phthalimides were determined on the basis of Lipiński’s rule. The biological properties were determined in terms of their cyclooxygenase (COX) inhibitory activity. Three compounds showed greater inhibition of COX-2, three compounds inhibited COX-1 more strongly than the reference compound meloxicam. From the obtained results, the affinity ratio COX-2/COX-1 was calculated. Two compounds had a value greater than that of meloxicam. All tested compounds showed oxidative or nitrosan stress (ROS and RNS) scavenging activity. The degree of chromatin relaxation outside the cell nucleus was lower than the control after incubation with all test compounds. The newly synthesized phthalimide derivatives showed no cytotoxic activity in the concentration range studied (10–90 µM). A molecular docking study was used to determined interactions inside the active site of cyclooxygenases.

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The 2-hydroxy-3-(4-aryl-1-piperazinyl)propyl Phthalimide Derivatives as Prodrugs—Spectroscopic and Theoretical Binding Studies with Plasma Proteins

Marciniak

Kotynia

Szkatuła

et al. 2022

IJMS

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Many publications in databases deal with the interactions of new drugs with albumin. However, it is not only albumin that is responsible for binding pharmaceutical molecules to proteins in the human body. There are many more proteins in plasma that are important for the study of the ADME pathway. Therefore, in this study, we have shown the results of the interactions between the plasma proteins albumin, orosomucoid, and gamma globulins and non-toxic anti-inflammatory phthalimide analogs, which due to the promising obtained results, may be potential candidates in the group of analgesic and anti-inflammatory drugs. Using spectroscopic methods and molecular modeling, we showed that all four tested compounds form complexes with the analyzed proteins. The formation of a complex with proteins raises the pharmacological efficacy of the drug. Therefore, the obtained results could be a step in the study of the pharmacokinetics and pharmacodynamics of new potential pharmaceuticals.

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Bioresearch of New 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones

Cited by 3 publications

References 15 publications

An Overview of the Biological Activity of Pyrrolo[3,4-c]pyridine Derivatives

An Overview of the Biological Activity of Pyrrolo[3,4-c]pyridine Derivatives

A New N-Substituted 1H-Isoindole-1,3(2H)-Dione Derivative—Synthesis, Structure and Affinity for Cyclooxygenase Based on In Vitro Studies and Molecular Docking

The 2-hydroxy-3-(4-aryl-1-piperazinyl)propyl Phthalimide Derivatives as Prodrugs—Spectroscopic and Theoretical Binding Studies with Plasma Proteins

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