Potential Growth Antagonists. I. Hydantoins and Disubstituted Glycines^1,2

Novel Mannich Bases, 5‐Arylimidazolidine‐2,4‐dione Derivatives with Dual 5‐HT1A Receptor and Serotonin Transporter Affinity

“…The designed series of 5‐arylhydantoin derivatives was prepared according to the synthetic routes shown in Scheme . The appropriate imidazolidine‐2,4‐diones were obtained from the 2‐methoxybenzaldehyde and 5‐fluoro‐2‐methoxybenzaldehyde by means of the Bucherer–Berg reaction with modifications described by Goodson et al 12. In the next step, aminoalkylation of the acidic proton of 5‐arylhydantoins carried out in the presence of formaldehyde and substituted 1‐phenylpiperazine enabled to obtain final compounds 3 – 10 .…”

“…The imidazolidine‐2,4‐diones ( 1 , 2 ) were prepared from the aldehyde by Bucherer–Bergs reaction with modifications described by Goodson et al 12. A solution of aldehyde (330 mmol) and ammonium carbonate (1 mol) in ethanol (330 mL) and water (220 mL) was warmed to 50°C, at which time potassium cyanide (350 mmol) dissolved in 50 mL of water was dropped in over a period of 15 min.…”

Is the optical rotation sign/absolute configuration relationship still a problem? Examples taken from unnatural quaternary aminoacids

“…12,13 Preferential crystallization using the auto seeded programmed polythermic preferential crystallization (AS3PC) method 14 at the hydantoin stage afforded each enantiomer in optically pure form: 15 hydrolysis of hydantoin (þ)-2b in basic conditions afforded the corresponding aminoacid (þ)-a-methyl-a-(p-bromophenyl)glycine 1b with a complete conversion. 16,2 Preparative HPLC of an aliquot allowed us to get rid of any sodium chloride, in order to ensure chemical purity and therefore an accurate measurement of the optical rotation of the aminoacid; apart from the sign of the optical rotation, large discrepancies could also be found in the various optical rotations reported in the literature for a-methyl-a-phenylglycine (Fig.…”

Aminolysis and Polymerization of 3‐(p‐Toluenesulfonoxy)Hydantoin

“…It is somewhat soluble in dimethylsulfoxide and swells in dimethylformamide and formamide. The polymer may be of biological interest as it contains both the biological active group hydantoin [4] and the carbazide group which exhibits therapeutic and other biological activities [5]. 5-Isopropyl-3-(p-toluenesulfonoxy)hydantoin did not undergo the same kind of polymerization.…”