Investigations on the synthesis and pharmacological properties of 4-alkoxy-2-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl]-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones

Sladowska, H; Filipek, Barbara; Szkatuła, Dominika; Sabiniarz, Aleksandra; Kardasz, Małgorzata; Potoczek, Joanna; Sieklucka-Dziuba, M; Rajtar, G; Kleinrok, Z; Lis, Tadeusz

doi:10.1016/s0014-827x(02)01302-2

Cited by 23 publications

(44 citation statements)

References 5 publications

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“…In this paper, it is studied that the derivatives of 4-alkoxy-2-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl]-6-methyl-1H-pyrrolo [3,4-c] ). It has been interesting to observe that in this test, the investigated imides have displayed superior activity to that, presented by ASA and Morphine (two reference substances-ED 50 for ASA was 39.15 and for Morphine -2.44 mg kg -1 ) [10,11]. On other hand, solid form diversity of pharmaceutical substances may influence the efficacy and safety of drug products.…”

Section: Introductionmentioning

confidence: 89%

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Synthesis and DSC study a new pyridinedicarboximide diones derivatives, obtained under various conditions

Krzy

2014

J Therm Anal Calorim

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The series of three 4-alkoxy-2-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl]-6-methyl-1H-pyrrolo [3,4-c] pyridine-1,3(2H)-diones were synthesized. The structures of all formed compounds were identified by elemental analysis, FTIR, and 1 H NMR. The synthesized compounds were studied using differential scanning calorimetry and thermogravimetric analysis in order to determine the existence of multiple solid-state forms. Our measurements showed that the solvent, mechanical treatment, and quenching are the important factors. Two stable and one metastable modification were detected. Additionally, DFT calculations were performed.

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Section: Introductionmentioning

confidence: 89%

“…Details of preparation are given in Ref. [10]. The final compounds were crystallized from ethanol and toluene.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and DSC study a new pyridinedicarboximide diones derivatives, obtained under various conditions

Krzy

2014

J Therm Anal Calorim

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“…Over the last decade, many similar compounds with structural modifications have been synthesised. The relationship between structure and pharmacological properties were investigated [4,5]. In the 'writhing syndrome' and 'hot plate' tests of those compounds, they have exhibited potent analgesic activity, which was superior to that of acetylsalicylic acid.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and thermal study of new N-substituted 1H-pyrrolo[3,4-c]pyridine-1,3(2H)diones of Mannich base type

Krzyżak

Szczęśniak-Sięga

Szkatuła

et al. 2011

J Therm Anal Calorim

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The new derivatives of 3,4-pyridinedicarboximide were synthesised. Experimental measurements were carried out using 1 H NMR spectra, IR spectra, elemental analyses and differential scanning calorimetry. The purpose of this study was to study the thermal stability of these four new compounds and to establish a solid-state polymorphism. Measurements were carried out for samples obtained from ethanol and n-hexane and after a long-time storage.

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“…[1,2] In the "writhing syndrome" and "hot plate" tests all compounds studied (I -V) ( Figure 1) exhibited potent analgesic activity, which was superior to that of acetylsalicylic acid. What's more, the results of the "writhing syndrome" test indicate that the compounds I-IV were more potent than morphine.…”

Section: Introductionmentioning

confidence: 99%

“…They probably play a role in the mechanism of action of these imides. [1,2] I. Muszalska et al 2104 Our investigations were based on our previous kinetic studies on stability and degradation of compounds I-III [3 -8] and the knowledge of other aryldicarboximides, such as thalidomide, [9 -12] buspirone, [13 -17] a new derivative of phthalimide, [18] their analogues, pro-drugs, and metabolites.…”

Section: Introductionmentioning

confidence: 99%

Chromatographic Separation of Derivatives of 4‐Alkoxy‐6‐methyl‐1H‐pyrrolo[3,4‐c]pyridine‐1,3(2H)‐dione by TLC and HPLC

Muszalska

Górski

Sladowska

et al. 2007

Journal of Liquid Chromatography & Related Technologies

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Five derivatives of 4-alkoxy-6-methyl-pyrrolo[3,4-c]pyridine-1,3-dione were separated by TLC and HPLC methods using silica gel 60 F 254 plates, analytical columns: LiChrosorb w RP-8 (250 Â 4 mm, 5 mm) and LiChrospher w 100 RP-18 (250 Â 4 mm, 5 mm), respectively. From the seven remaining mobile phases, three were offered for use with two-dimensional TLC. The values of separation parameter (a), constant of the pair separation (R F a ), and DR F of two neighbouring spots on each chromatogram were defined. The mobile phase C (butan-1-ol -propan-2-ol -cyclohexane-acetic acid (1.05 kg/L); 6:3:2:1, v/v/v/v) was used in the first dimension but mobile phase D (chloroform -propan-2-ol-acetic acid (1.05 kg/L); 40:15:6, v/v/v) and/or E (chloroform -cyclohexane -propan-2-ol-acetic acid (1.05 kg/L); 20:20:15:6, v/v/v/v) were used in the second dimension. The main validation parameters (linearity, limits of quantification (LOQ) and determination (LOD), repeatability of retention times) were evaluated for the analysis of all of the investigated derivatives in their mixture, by using RP-HPLC with UV detection at 254 nm (LiChrospher w 100 RP-18 column; acetonitrile -methanol -phosphate buffer, pH 7 (45:15:40), 1.5 mL/min).

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Investigations on the synthesis and pharmacological properties of 4-alkoxy-2-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl]-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones

Cited by 23 publications

References 5 publications

Synthesis and DSC study a new pyridinedicarboximide diones derivatives, obtained under various conditions

Synthesis and DSC study a new pyridinedicarboximide diones derivatives, obtained under various conditions

Synthesis and thermal study of new N-substituted 1H-pyrrolo[3,4-c]pyridine-1,3(2H)diones of Mannich base type

Chromatographic Separation of Derivatives of 4‐Alkoxy‐6‐methyl‐1H‐pyrrolo[3,4‐c]pyridine‐1,3(2H)‐dione by TLC and HPLC

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