ISSN 1070-3632, Russian Journal of General Chemistry, 2017, Vol. 87, No. 3, pp. 523–529. © Pleiades Publishing, Ltd., 2017. 523 Synthesis of Some Novel 2-Thioxoimidazolidin-4-one Substituted Glycosyl Hydrazone Derivatives 1 N. M. Khalifa a,b * , M. A. Al-Omar a , A. A. Sediek c,d , and A. E. Amr a,c a Pharmaceutical Chemistry Department, Drug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh, 11451 Saudi Arabia *e-mail: nagykhalifa@hotmail.com b Department of Therapeutical Chemistry, Pharmaceutical and Drug Industries Division, National Research Centre, Dokki 12622, Cairo, Egypt c Chemical Industries Division, National Research Centre, Dokki, Cairo, 12622 Egypt d Chemistry Department, Faculty of Sciences and Arts, Al-Kamil Branch, University of Jeddah, Jeddah, Saudi Arabia Received December 30, 2015 Abstract—A series of novel 2-thioxoimidazolidine glycosides were prepared via reaction of the key intermediate 2-(benzylsulfanyl)-5-[4-(3-hydroxypropoxy)-3-(methoxybenzylidene)]-3-phenyl-1H-imidazol-4-one with different sugar aldose or sugar hydrazones to give the corresponding glycosides. The newly synthesized compounds were confirmed by physical and spectral data. Keywords: 2-thioxoimidazolidin-4-one derivatives, sugar hydrazones, N-glycosides 1 The text was submitted by the authors in English. 2-Thioxoimidazolidinones are a significant class of heterocyclic structures found in a number of biolo- gically active natural products with diverse medical applications, specifically, as antitumor, antischisto- somiatic, anti-inflammatory, hypoglycemic, antiviral, antitubercular, analgesic, anticonvulsant, antimicrobial, and antifungal agents [1–9]. Furthermore, 3,5-di- substituted-2-thioxoimidazolidinones and their glycoside derivatives were found to display a high potency against herpes simplex (HSV) and human immuno- deficiency viruses (HIV), leukemia, and prostate cancer [10]. On the other hand, carbohydrates and their analogs have attracted increasing interest, because many of them are widely used as components of various bioactive products, such as antibiotics [11] and biopolymers [12]. In view of the above considerations and proceeding with our studies [13‒17] on the attachment of carbohydrate residues to heterocycles, we report herein the preparation of new glycosides linked 2-thioxoimidazolidines moiety. The synthetic pathways leading to the target glycosides are outlined in (Schemes 1‒3). Alkylation of 5-[4-(3-hydroxypropoxy)-3-(methoxybenzylidene)]- 3-phenyl-2-thioxoimidazolidin-4-one (1) with benzyl chloride in a basic medium give the key intermediate 2-(benzylsulfanyl)-5-[4-(3-hydroxypropoxy)-3-(methoxy- benzylidene)]-3-phenyl-1H-imidazol-4-one (2). Com- pound 2 was allowed to react with with nicotinic hydrazide or 2-aminobenzimidazole in acetic acid to afford the corresponding 2-amino derivatives 3 and 4, respec-tively (Scheme 1). Compound 2 was also reacted with hydrazine hydrate to afford 2-hydrazino derivative 5 which was reacted with a series of monosaccharides, namely, D- glucose, D-galactose, D-mannose, D-xylose, or L- arabinose to give the corresponding glycosylhydrazino derivatives 6a–6e. Oxidation of compound 2 with hydrogen peroxide gave the corresponding sulfanyl derivative 7 (Scheme 2). Furthermore, compound 2 was reacted with sugar hydrazine derivatives 8a–8e to afford the cor- responding 2-[(2-(E)-polyhydroxyalkylidene)hydrazono]- 5-[(Z)-arylidene]imidazolidin-4-one derivatives 9a–9e (Scheme 3). The compositions and structures of the prepared products were confirmed by the elemental analyses and spectral data. EXPERIMENTAL Melting points were determined with open capillary tubes using Griffin melting point apparatus and are DOI: 10.1134/S1070363217039239