ChemInform Abstract: Synthesis and Properties of 2‐(4‐Substituted)butyl Derivatives of Some 2,3‐Dihydro‐1,3‐dioxo‐1H‐pyrrolo[3,4‐c]pyridines.

Sladowska, H; Szkatuła, Dominika; Filipek, Barbara; Maciąg, Dorota; Sapa, Jacek; Zygmunt, Małgorzata

doi:10.1002/chin.200118125

Cited by 5 publications

(23 citation statements)

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“…Synthetic scheme of the studied compounds, as shown in Scheme 1 . The compounds 2 , 3 and A were obtained according to the literature data [ 10 , 11 , 12 , 13 ]. Imide 2 is the starting product for derivatives A , B and C and many other substances described earlier [ 10 , 14 , 15 ].…”

Section: Resultsmentioning

confidence: 99%

“…To compare the biological properties of both basic systems, it was decided to synthesize analogues of the previously described derivatives containing the same amino residues: 1-phenylpiperazine ( A ), 1-(2-methoxyphenyl)piperazine ( B ) and 1-(3-trifluoromethyphenyl)piperazine ( C ) [ 9 ]. The presence of an acidic proton atom at the imide nitrogen atom in position 2 makes it possible to carry out the aminomethylation reaction according to the mechanism described by Mannich [ 13 , 16 ]. The reaction was carried out using aqueous solution of formaldehyde (HCHO) and N-arylpiperazines (commercial products Sigma-Aldrich) at the reflux temperature of tetrahydrofuran (THF) for several hours (method I, Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Cyclooxygenases Inhibition Activities and Interactions with BSA of N-substituted 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones Derivatives

et al. 2020

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Inhibition of cyclooxygenase is the way of therapeutic activities for anti-inflammatory pharmaceuticals. Serum albumins are the major soluble protein able to bind and transport a variety of exogenous and endogenous ligands, including hydrophobic pharmaceuticals. In this study, a novel N-substituted 1H-pyrrolo[3–c]pyridine-1,3(2H)-diones derivatives were synthesized and biologically evaluated for their inhibitory activity against cyclooxygenases and interactions with BSA. In vitro, COX-1 and COX-2 inhibition assays were performed. Interaction with BSA was studied by fluorescence spectroscopy and circular dichroism measurement. The molecular docking study was conducted to understand the binding interaction of compounds in the active site of cyclooxygenases and BSA. The result of the COX-1 and COX-2 inhibitory studies revealed that all the compounds potentially inhibited COX-1 and COX-2. The IC50 value was found similar to meloxicam. The intrinsic fluorescence of BSA was quenched by tested compounds due to the formation of A/E–BSA complex. The results of the experiment and molecular docking confirmed the main interaction forces between studied compounds and BSA were hydrogen bonding and van der Waals force.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis, Cyclooxygenases Inhibition Activities and Interactions with BSA of N-substituted 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones Derivatives

et al. 2020

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“…The starting materials for the synthesis of compounds 9-15 were 4-methoxy-and 4-ethoxy-6methyl-1H-pyrrolo [3.4-c]pyridine-1,3(2H)-diones (3,4),and in the case of imide 8, it was an intermediate 4-methoxy-2,3-dihydro-6-methyl-2-(4-bromobutyl)-1,3-dioxo-1H-pyrrolo [3,4c]pyridine (5) synthesized previously [5,8]. The results were discussedin detail in our previous works [5][6][7][8][9][10][11][12][13][14]. As previously established, the shortening of the alkyl linker between the basic center of the arylamine and the cyclic imide moiety resulted in derivatives with similar biological properties [8].…”

Section: Chemistrymentioning

confidence: 99%

“…The starting materials for the synthesis of compounds 9-15 were 4-methoxy-and 4-ethoxy-6-methyl-1H-pyrrolo [3.4-c]pyridine-1,3(2H)-diones (3,4), and in the case of imide 8, it was an intermediate 4-methoxy-2,3-dihydro-6-methyl-2-(4-bromobutyl)-1,3-dioxo-1H-pyrrolo [3,4-c]pyridine (5) synthesized previously [5,8].…”

Section: Chemistrymentioning

confidence: 99%

“…N-Substituted Derivatives of 4-alkoxy-6-methyl-1H-pyrrolo [3,4-c]pyridine-1,3(2H)-diones (5, 6a, 6b, 7a, 7b) The synthesis of the final compounds was carried out in two stages ( Figure 2). The starting reagents in the first stage of the synthesis, 4-methoxy/4-ethoxy-6-methyl-1H-pyrrolo[3, 4-c]pyridine-1,3(2H)-diones [8] and 1,2-dibromoethane (6a,6b), 1-bromo -2-chloroethane (7a,7b),1,2-dibromobutane (5) [5], were used. The chemical structure of the obtained final products is presented in Table 1 and Figure 2.…”

Section: Chemistrymentioning

confidence: 99%

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

et al. 2020

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The subject of the work was the synthesis of new derivatives of1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione with potential analgesic and sedative activity. Eight compounds werereceived. The analgesic activity of the new compounds was confirmed in the “hot plate” test and in the “writhing” test. All tested imides 8–15 were more active in the “writhing” test than aspirin, and two of them, 9 and 11, were similar to morphine. In addition, all of the new imides inhibited the locomotor activity in mice to a statistically significant extent, and two of them also prolonged the duration of thiopental sleep.On the basis of the results obtained for the previously synthesized imides and the results presented in this paper, an attempt was madeto determine the relationship between thechemical structure of imides and their analgesic and sedativeproperties.

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Synthesis and antinociceptive activity of four 1H‐isoindolo‐1,3(2H)‐diones

Dziubina

Szkatuła

Gdula‐Argasińska

et al. 2022

Archiv der Pharmazie

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The present study aimed to design and synthesize a series of 2-hydroxy-3-(4-aryl-1piperazinyl)propyl phthalimide derivatives, which are analogs of 1H-pyrrolo[3,4-c] pyridine-1,3(2H)-dione derivatives with proven analgesic effect. In accordance with the basic principle proposed by Lipinski's rule, the probable bioavailabilities of the F1-F4 phthalimides were assessed. The obtained values indicate good absorption after oral administration and the ability to cross the blood-brain barrier. The four compounds F1-F4 differing in the type of pharmacophore in the phenyl group of the 2-hydroxy-3-(4-aryl-1-piperazinyl)propyl on the imide nitrogen atom (R, F1-F3) and the 4-benzhydryl analog (F4) were selected for in vitro and in vivo studies. Based on the in vitro studies, the effects of compounds F1-F4 on cell viability/proliferation and COX-2 levels were evaluated. Moreover, using in vivo methods, the compounds were tested for antinociceptive activity in models of acute pain (the writhing and the hot-plate tests) in mice. Their influence on the motor coordination effect and locomotor activity was also tested. The obtained results revealed that the compounds F1-F4 strongly suppress the pain of peripheral origin and to a lesser extent (F1-F3) pain of central/supraspinal origin. In the in vitro studies, F1-F4 reduced the COX-2 level in lipopolysaccharide-activated RAW 264.7 cells, which suggests their anti-inflammatory activity.

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ChemInform Abstract: Synthesis and Properties of 2‐(4‐Substituted)butyl Derivatives of Some 2,3‐Dihydro‐1,3‐dioxo‐1H‐pyrrolo[3,4‐c]pyridines.

Cited by 5 publications

References 0 publications

Synthesis, Cyclooxygenases Inhibition Activities and Interactions with BSA of N-substituted 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones Derivatives

Synthesis, Cyclooxygenases Inhibition Activities and Interactions with BSA of N-substituted 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones Derivatives

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

Synthesis and antinociceptive activity of four 1H‐isoindolo‐1,3(2H)‐diones

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