S-Glucosylated hydantoins as new antiviral agents

Abstract

S-Glycosylation took place on reaction of 5-alkylidene- and 5-arylidene-3-aryl-2-thiohydantoins with glycosyl halides under alkaline conditions. Bisglucosylation also took place when N-3 unsubstituted hydantoins were reacted. The bisglucosylated hydantoins produced N-3 glucosylated hydantoins on treatment with ammonia in methanol. In antiviral studies the most active compounds against both HSV-1 and HSV-2 were 5-(2-thienylmethylene)-3-phenyl-2-(2,3,4,6- tetra-O-acetyl-beta-D-glucopyranosyl)-2-thiohydantoin and 5-(2-thienylmethylene)-3-(4-chlorophenyl)-2-(2,3,4,6-tetra-O-acety l-beta-D- glucopyranosyl)-2-thiohydantoin.

Reactivity of 2-Thiohydantoins Towards Various Electrophilic Reagents: Applications to the Synthesis of New 2-Ylidene-3,5-dihydro-4H-imidazol-4-ones.

“…The solvent was removed in vacuo and diethyl ether (100 mL) was poured into the crude reaction mixture. Insoluble salts were filtered off and the filtrate was dried over MgSO 4 . The solvent was eliminated in a rotary evaporator and the crude reaction mixture gave oil that crystallized on standing .…”

“…Furthermore, several 5-arylidene-3-aryl-2-thiohydantoins and their Sglucosylated derivatives [3] show potent activity against the herpes simplex virus (HSV) [4] and the human immunodeficiency virus (HIV) [5].…”

Solvent-free highly regioselective Michael addition of phenytoin to α,β-unsaturated esters in the presence of TBAB under ultrasound irradiation

“…These studies indicate that hydantoin and its derivatives have a broad range of biological activities including anticonvulsants, 2 antiarithmics, 3 antitumor, 4 antidepressants, 5 and antiviral agents. 6 Phenytoin 1 (5,5-diphenylhydantoin, DPH) is one of the best known derivatives of hydantoin. This heterocycle is a useful pharmacological compound and extensively used as an anticonvulsant agent, 7 treatment of epileptic seizures, 8,9 epidermolysis bullosa, 10 inflammatory conditions, case of anticonvulsant activity of DPH, it has been established that the site of the action of this compound is the neuronal voltage-sensitive sodium channel, though no more information about the location and nature of this site has been reported.…”

Synthesis, Spectroscopy and Electrochemistry of New 3-(5-Aryl-4,5-Dihydro-1H-Pyrazol-3-yl)-4-Hydroxy-2H-Chromene-2-One 4, 5 as a Novel Class of Potential Antibacterial and Antioxidant Derivatives

“…The activity of a variety of chalcones as potent tyrosinase inhibitors and antioxidants has been also reported which are, thus, used as new depigmentation agents [5]. Nitrogen heterocycles containing chalcone moiety have been reported as active compounds against herpes simplex virus-1 (HSV-1) and human immunodeficiency virus 1 (HIV-1) [6,7]. This class of compounds also exhibits cytotoxic activity towards leukemia cell lines [8,9].…”