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Phthalimidine, 2-(2,6-dioxopiperiden-3-yl).

Names

[ CAS No. ]:
26581-81-7

[ Name ]:
Phthalimidine, 2-(2,6-dioxopiperiden-3-yl).

[Synonym ]:
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

Biological Activity

[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.

Chemical & Physical Properties

[ Density]:
1.393g/cm3

[ Boiling Point ]:
534.3ºC at 760mmHg

[ Molecular Formula ]:
C13H12N2O3

[ Molecular Weight ]:
244.24600

[ Flash Point ]:
276.9ºC

[ Exact Mass ]:
244.08500

[ PSA ]:
69.97000

[ LogP ]:
0.66140

Synthetic Route

Click to get detail synthetic route

Related Compounds