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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.
In 2001, just a few years after Celgene obtained approval for Thalomid in treating a condition associated with leprosy, a Boston researcher discovered that 3-amino-thalidomide showed promise in ...
C 6 H 4 (CO) 2 NH + RX + NaOH → C 6 H 4 (CO) 2 NR + NaX + H 2 O. The amine is commonly liberated using hydrazine: C 6 H 4 (CO) 2 NR + N 2 H 4 → C 6 H 4 (CO) 2 N 2 H 2 + RNH 2. Dimethylamine can also be used. [5] Some examples of phthalimide drugs include thalidomide, amphotalide, taltrimide, talmetoprim, and apremilast.
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]
In this approach: identify the chiral center, label the four atoms directly attached to the stereogenic center in question, assign priorities according to the sequence rule ( from 1 to 4), rotate the molecule until the lowest priority (number 4) substituent is away from the observer/viewer, draw a curve from number 1 to number 2 to number 3 ...
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).
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.
3-(5-Amino-2-methyl-4-oxoquinazolin-3-yl)piperidine-2,6-dione. CAS Number: 1015474-32-4; PubChem CID: ... or thalidomide analog studied to see if it is effective ...