Synthesis and nootropic activity of some 2,3-dihydro-1H-isoindol-1-one derivatives structurally related with piracetam |
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Authors: | Reyes Adelfo Huerta Leticia Alfaro Marisol Navarrete Andrés |
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Affiliation: | 1. Facultad de Estudios Superiores Zaragoza, Unidad Multidisciplinaria de Investigación Experimental, Universidad Nacional Autónoma de México, Batalla 5 de Mayo esquina Fuerte de Loreto, Ejército de Oriente, Iztapalapa 09230, México D.?F., México, (phone: +(55)?56230794;2. fax: +(55)?57736330);3. Facultad de Química, Departamento de Farmacia. Universidad Nacional Autónoma de México, México D.?F., 04510, México |
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Abstract: | Three 2,3‐dihydro‐1H‐isoindol‐1‐ones structurally related with piracetam (=2‐oxopyrrolidine‐1‐acetamide) have been synthesized and tested for their nootropic effects in the passive avoidance test in mice. Compounds (RS)‐ 2 , (R,R)‐ 3 , and (R,S)‐ 3 were obtained in good yields in only two steps starting from methyl dl ‐phthaloylalanine. Compound (RS)‐ 2 exhibited nootropic activity at lower doses than piracetam, used as reference drug, but it showed lower efficacy. Whereas diastereoisomers (R,R)‐ 3 and (R,S)‐ 3 were as potent as piracetam to revert amnesia induced by scopolamine, (R,S)‐ 3 showed lower efficacy than (R,R)‐ 3 . Only (R,R)‐ 3 showed myorelaxant effect at doses of 10 and 30 mg/kg; other compounds did not exhibit any anticonvulsant, sedative, myorelaxant, or impaired motor‐coordination effect in mice. These synthesized 2,3‐dihydro‐1H‐isoindol‐1‐one derivatives constitute a new kind of nootropic compounds. |
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Keywords: | Isoindolones, dihydro‐ Piracetam Nootropic activities |
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