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The thalidomide molecule is a synthetic derivative of glutamic acid and consists of a glutarimide ring and a phthaloyl ring (Figure 5). [15] [16] Its IUPAC name is 2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione and it has one chiral center [15] After thalidomide's selective inhibition of TNF-α had been reported, a renewed effort was put in thalidomide's clinical development.
Folpet, a phthalimide, is a commercial fungicide. [3]Phthalimide is used as a precursor to anthranilic acid, a precursor to azo dyes and saccharin. [2]Alkyl phthalimides are useful precursors to amines in chemical synthesis, especially in peptide synthesis where they are used "to block both hydrogens and avoid racemization of the substrates". [4]
Structure-activity studies revealed that amino substituted thalidomide had improved antitumor activity, which was due to its ability to directly inhibit both the tumor cell and vascular compartments of myeloma cancers. [18] This dual activity of pomalidomide makes it more efficacious than thalidomide in vitro and in vivo. [19]
Thalidomide, sold under the brand names Contergan and Thalomid among others, is an oral medication used to treat a number of cancers (e.g., multiple myeloma), graft-versus-host disease, and many skin disorders (e.g., complications of leprosy such as skin lesions).
[1] [2] [3] The reaction is named after the German chemist Siegmund Gabriel. [4] The Gabriel reaction has been generalized to include the alkylation of sulfonamides [5] and imides, followed by deprotection, to obtain amines (see Alternative Gabriel reagents). [6] [7] The alkylation of ammonia is often an unselective and inefficient route to amines.
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A general linear imide functional group. In organic chemistry, an imide is a functional group consisting of two acyl groups bound to nitrogen. [1] The compounds are structurally related to acid anhydrides, although imides are more resistant to hydrolysis.
Tris inhibits a number of enzymes, [10] [11] and therefore should be used with care when studying proteins. Tris can also inhibit enzyme activity via chelation of metal ions. [ 3 ]