124149-94-6

Upstream product

• 100-52-7 benzaldehyde 
• 120328-90-7 methyl (E)-N-benzylidenealaninate 
• 107-13-1 acrylonitrile 

Downstream Products

• 123979-17-9 N-(3-Methyl-2-oxo-piperidin-3-yl)-phthalamic acid 
• 64298-90-4 3-amino-3-methyl-piperidin-2-one 
• 81080-74-2 2-(2-cyanoethyl)alanine methyl ester 
• 113273-79-3 (2S,4R,5R)-4-Cyano-2-methyl-5-phenyl-pyrrolidine-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

5-Endo-Trig Cyclisation and 1,3-Anionic Cycloaddition in Arylimine Derivatives of α-Amino Acid Esters

Michael adducts of imines of α-amino acid esters are converted into a mixture of two stereoisomeric pyrrolidines by benzyltrimethylammonium methoxide (BTAM) apparently by a 5-endo-trig cyclisation.

(S)-form of α-methyl-N(α)-phthalimidoglutarimide, but not its (R)-form, enhanced phorbol ester-induced tumor necrosis factor-α production by human leukemia cell HL-60: implication of optical resolution of thalidomidal effects

The rate of racemization of N(α)-phthalimidoglutarimide (thalidomide) was determined as its half life to be 566 min at pH 7.4/37°C. This fast racemization of thalidomide resulted in no apparent difference between (S)- and (R)-forms of the compound on enhancing activity of phorbol ester-induced tumor necrosis factor (TNF)-α production by human leukemia HL-60 cells. Optically pure forms of structurally related analog of thalidomide, (S)- and (R)-α-methyl-N(α)-phthalimidoglutarimides, (methylthalidomides), which do not racemize under the physiological condition, were prepared. Only (S)-form of methylthalidomide, but not its (R)-form, elicited TNF-α production- enhancing effect, suggesting that the (S)-isomer of thalidomide would be the active form in terms of thalidomidal biological response modifying effects.