Chemistry Of Optically Active Cyanohydrins-Part 3:[ 1] Preparation And Reactions Of (R)-2-Hydroxy-2-(Naphthalen-1-Yl)Ethane- Nitrile Using (R)-Hydroxynitrile Lyase From Prunus Amygdalus. Antitumor And Antimicrobial Evaluation Of The New Products

CYANURATION of 1-naphthaldehyde (1) yielded the racemic... 2-hydroxy-2-(naphthalene-1-yl) ethanenitrile (R, S)-2. The same reaction can be completed by using acetone cyanohydrin (3) as a transcyanating agent. The optically active cyanohydrin enantiomer (R)-2 could be obtained by hydrocyanation of (1) in presence of (R)hydroxynitrile lyase (R)-Pa HNL [EC4.1.2.10] from almonds (Prunus amygdalus) as a chiral catalyst. Cyanohydrin 2 in its racemic and optically active forms reacts with the isocyanate reagents 4a-c to give the carbamate derivatives (R, S)-5 and (R)-5, respectively. On the other hand, the reaction of (R, S)-2 and (R)-2 with the isocyanate and/or isothiocyanate reagents 6a-e gave the 4-imino-2-oxazolidinone derivatives, (R, S)-8 and (R)-8, respectively. Moreover, derivatization of (R)-2 with (S)-Naproxen (R) chloride (S)-10 gave the respective diastereomer (R, 2S)-11. The postulated structures for the new products were supported with compatible elementary microanalyses and spectroscopic (IR, H-1 NMR, MS) measurements. The antitumor and antimicrobial activities of some selected racemic new products and their respective optically active analogues were also endeavored. The structure-activity relationship (SAR) was also discussed.