Thalidomide structure

Therapeutic Function Sedative, Hypnotic, Antiarthritic Chemical Name Phthalimide, N-(2,6-dioxo-3-piperidyl)-Common Name Thalidomide Structural Formula ... 

Exposure to the fetus in the first 2 weeks after conception may have an all or nothing effect (i.e., could destroy the embryo or have no ill effect). Exposure during the period of organogenesis (18 to 60 days postconception) may result in structural anomalies (e.g., methotrexate, cyclophosphamide, diethylstilbestrol, lithium, retinoids, thalidomide, certain antiepileptic drugs, and coumarin derivative). 

The structure of thalidomide contains a tetrahedral carbon atom (coloured red) attached to four different groups. This implies that thalidomide exhibits optical isomerism. 

Fig. 8.1 Structures of thalidomide, EM-12 and their metabolites which are all angiogenesis inhibitors and teratogens or potential teratogens.

Thalidomide was initially selected as Candidate K17. It was discovered from peptide research but promoted as being structurally related to barbiturate with hypnotic properties, beyond those of the classic barbiturate Luminal, but without toxicity. 

More recent studies have indicated a probable mechanism that relies on the interaction of thalidomide with DNA. The phthalimide double-ring structure (Fig. 7.74) is relatively flat and can intercalate with DNA forming a stacked complex. Furthermore, observations were made that thalidomide... 

Much toxicological investigation has occurred with respect to a series of pesticide chemicals known as Captan, Folpet, and Difolatan. The molecular structure of these pesticides is exceedingly similar to that of thalidomide. Thalidomide is the... 

Figure 3.25 Chemical structures and optimized geometries of (/ )- and (S)-thalidomide.

In any case however, antipodal helices cause countercurrent spectra of the optical rotation, so that the observation of just a single Cotton effect is sufficient to discriminate the antipodes and, in case, enantiomeric solutes. For such an experiment the choice of the infrared spectral range is no longer dictated by the structure period but by the presence of suitable transition moments. The low demand for the chiral solute to be characterized (Korte, 1978) is exemplified by Fig. 4.6-14. In the 20 im wide sample cell an area of 3 mm times 3 mm was filled with approximately 200 pg solution containing circa 0.2 pg of either S-(-) or R-(-i-) Thalidomide (Contergan) in a nematic solvent. In the spectral interval shown, at least three oppositely shaped ACE are found, the pronounced one around 836 cm is related to the 7 (C- H), phenyl-H out-of-plane vibration of the... 

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