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

Modify Date: 2024-01-16 22:12:55

Phthalimidine, 2-(2,6-dioxopiperiden-3-yl). Structure
Phthalimidine, 2-(2,6-dioxopiperiden-3-yl). structure
Common Name Phthalimidine, 2-(2,6-dioxopiperiden-3-yl).
CAS Number 26581-81-7 Molecular Weight 244.24600
Density 1.393g/cm3 Boiling Point 534.3ºC at 760mmHg
Molecular Formula C13H12N2O3 Melting Point N/A
MSDS N/A Flash Point 276.9ºC

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


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].

 Names

Name 3-(1-Oxo-1,3-dihydro-2H-isoindol-2-yl)-2,6-piperidinedione
Synonym More Synonyms

  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
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

 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
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