26581-81-7

26581-81-7 structure

Name: Phthalimidine, 2-(2,6-dioxopiperiden-3-yl).
Chemical Name: 3-(1-Oxo-1,3-dihydro-2H-isoindol-2-yl)-2,6-piperidinedione
CAS Number: 26581-81-7
Molecular Formula: C₁₃H₁₂N₂O₃
Molecular Weight: 244.24600
Catalog: Research Areas Cancer
Create Date: 2018-06-17 12:05:34
Modify Date: 2024-01-16 22:12:55
2-(2,6-Dioxopiperidin-3-yl)phthalimidine (EM-12), a teratogenic Thalidomide analogue, is more active than Thalidomide and is much more stable for hydrolysis. 2-(2,6-Dioxopiperidin-3-yl)phthalimidine enhances 1,2-dimethylhydrazine-induction of rat colon adenocarcinomas[1][2].

Name	3-(1-Oxo-1,3-dihydro-2H-isoindol-2-yl)-2,6-piperidinedione
Synonyms	2-(1-Oxoisoindolin-2-yl)-glutarimid 2-(2,6-dioxopiperdin-3-yl)-1-oxoisoindoline 3-[1,3-dihydro-1-oxo-2H-isoindol-2-yl]-2,6-dioxopiperidine (+/-)-Hydroxythalidomide 5-Hydroxythalidomide 2-(2,6-dioxo-3-piperidinyl)-5-hydroxy-1H-isoindole-1,3(2H)-dione 1H-Isoindole-1,3(2H)-dione,2-(2,6-dioxo-3-piperidinyl)-5-hydroxy 2-(2,6-dioxo-piperidin-3-yl)-5-hydroxy-isoindole-1,3-dione 3-(1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione

Description	2-(2,6-Dioxopiperidin-3-yl)phthalimidine (EM-12), a teratogenic Thalidomide analogue, is more active than Thalidomide and is much more stable for hydrolysis. 2-(2,6-Dioxopiperidin-3-yl)phthalimidine enhances 1,2-dimethylhydrazine-induction of rat colon adenocarcinomas[1][2].
Related Catalog	Research Areas >> Cancer Signaling Pathways >> Others >> Others
In Vivo	Young male Sprague-Dawley rats in 3 groups are fed a basal diet supplemented with 0.10 wt. % each of thalidomide and its imide-analog of much higher teratogenicity, 2-(2,6-Dioxopiperidin-3-yl)phthalimidine. Following an induction period of 17 days on the diets, all animals are injected subcutaneously with 1,2-dimethylhydrazine at 20 mg/kg for a total of 20 weekly doses and killed on week 18 after the 20th injection. 2-(2,6-Dioxopiperidin-3-yl)phthalimidine-fed group elicits statistically significant increases both in the total and ascending colon-based adenocarcinomas as compared with the control findings, in keeping with its greater teratogenicity and embryotoxicity[2].
References	[1]. Merker HJ, et al. Embryotoxic effects of thalidomide-derivatives in the non-human primate Callithrix jacchus. I. Effects of 3-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-dioxopiperidine (EM12) on skeletal development. Arch Toxicol. 1988;61(3):165-179. [2]. Gershbein LL. The thalidomide analog, EM 12, enhances 1,2-dimethylhydrazine-induction of rat colon adenocarcinomas. Cancer Lett. 1991;60(2):129-133.