24666-53-3

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2-[2,6-dioxo-1-(phenylmethyl)-3-piperidinyl]-
• CAS NO: 24666-53-3
• Molecular Formula: C20H16N2O4
• Molecular Weight: 348.358
• Mol File: 24666-53-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2-[2,6-dioxo-1-(phenylmethyl)-3-piperidinyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2-[2,6-dioxo-1-(phenylmethyl)-3-piperidinyl]-(24666-53-3)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2-[2,6-dioxo-1-(phenylmethyl)-3-piperidinyl]-(24666-53-3)

Safety Data

• Hazardous Substances Data: 24666-53-3(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 3343-28-0 N-phthaloylglutamic acid anhydride 
• 85-44-9 phthalic anhydride 
• 50-35-1 thalidomide 
• 100-44-7 benzyl chloride 
• 6349-98-0 N-phthalylglutamic acid 
• 94547-37-2 N⁵-benzyl-N²,N²-phthaloyl-glutamine 

Downstream Products

• 26840-61-9 1-benzyl-3-(1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione 

Relevant articles and documents

Synthesis and biological evaluation of thalidomide derivatives as potential anti-psoriasis agents

Several thalidomide derivatives were synthesized and evaluated for their anti-inflammatory activity. Introduction of the benzyl group to the parent thalidomide is unfavorable in which 2-(1-benzyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione (4a) was inactivated. However, the inhibitory activities on TNF-α and IL-6 expression in HaCaT cells were improved by the substitution of a chloro-or methoxy-group at the phenyl position of 4a. The IL-6 inhibitory activity decreased in an order of 5c (69.44%) > 4c (48.73%) > 6c (3.19%) indicating the 3-substituted derivative is more active than the 4-substituted counterpart, which in turn is more active than the 2-substituted counterpart. Among them, 2-[1-(3-chlorobenzyl)-2,6-dioxopiperidin-3-yl]isoindoline-1,3-dione (5c) was found to inhibit TNF-α and IL-6 expression in HaCaT cells with a higher potency than thalidomide and no significant cell cytotoxicity was detected at 10 μM. In psoriasis, Compound 5c reduced IL-6, IL-8, IL-1β and IL-24 in imiquimod-stimulated models. Our results indicated that compound 5c is a potential lead of novel anti-psoriasis agents. Structural optimization of compound 5c and its in vivo assay are ongoing.

Method of treating abnormal concentrations of TNF α

Compounds of the structure STR1 wherein R is selected from the group consisting of hydrogen, alkyl radicals of 1-6 carbon atoms, the phenyl radical, and the benzyl radical; and wherein R' is selected from the group consisting of the phthalimido radical and the succinimido radical and of the structure STR2 wherein X is CH2 or C=O; R" is H, --CH2 CH3, --C6 H5, --CH2 C6 H5, --CH2 CH=CH2, or STR3 and hydrolysis products of said compounds wherein R" is H and the piperidino ring or both the piperidino and the imido ring are hydrolyzed are useful for the control of abnormal concentrations of TNF α manifested in septic shock, cachexia and HIV infection without substantially effecting the concentration of other cytokines.