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

• Published in: Farmaco (Società chimica italiana : 1989) Vol. 57; no. 11; pp. 897 - 908
• Main Authors: Śladowska, Helena, Filipek, Barbara, Szkatuła, Dominika, Sabiniarz, Aleksandra, Kardasz, Małgorzata, Potoczek, Joanna, Sieklucka-Dziuba, Maria, Rajtar, Grażyna, Kleinrok, Zdzisław, Lis, Tadeusz
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier SAS 01.11.2002; Elsevier; Elsevier Science
• Subjects: 4-Alkoxy-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones; Analgesic and sedative activities; Analgesics; Analgesics, Non-Narcotic - chemical synthesis; Analgesics, Non-Narcotic - pharmacology; Analgesics, Non-Narcotic - toxicity; Animals; Biological and medical sciences; Blood Pressure - drug effects; Crystallography, X-Ray; Derivatives of 7-aza-4-azoniaspiro[3.5]nonane chloride; Dose-Response Relationship, Drug; Female; Hypnotics. Sedatives; Indicators and Reagents; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Male; Medical sciences; Mice; Models, Molecular; Molecular Conformation; Motor Activity - drug effects; N-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl] derivatives; Neuropharmacology; Pain Measurement - drug effects; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Piperazines - chemical synthesis; Piperazines - pharmacology; Psychology. Psychoanalysis. Psychiatry; Psychopharmacology; Pyridones - chemical synthesis; Pyridones - pharmacology; Pyrroles - chemical synthesis; Pyrroles - pharmacology; Rats; Rats, Wistar; Science & Technology; Structure-Activity Relationship; Synthesis; Synthesis; Derivatives of 7-aza-4-azoniaspiro[3.5]nonane chloride; Analgesic and sedative activities; 4-Alkoxy-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones; N-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl] derivatives; synthesis; ANALGESIC ACTION; 4-alkoxy-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones; analgesic and sedative activities; derivatives of 7-aza-4-azoniaspiro[3.5]nonane chloride; DERIVATIVES; Aminoalcohol; Rat; Nitrogen heterocycle; Psychotropic; Rodentia; Imide; Locomotion; Vertebrata; Mammalia; Analgesic; Structure activity relation; Mouse; Animal; Bicyclic compound; Arterial pressure; Piperazine derivatives; Sedative; Secondary alcohol; Chemical synthesis
• ISSN: 0014-827X; 1879-0569
• DOI: 10.1016/S0014-827X(02)01302-2

Synthesis of 2-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl] derivatives of 4-alkoxy-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones (8–12) is described. The chlorides used in the above synthesis can exist in two isomeric forms: chain (18–20) and cyclic (19a, 20a). The compounds 8–12 exhibited potent analgesic activity which was superior than that of acetylsalicylic acid in two different tests. Most of the investigated imides suppressed significantly spontaneous locomotor activity in mice.