Synthesis and Biological Evaluation of S-Substituted Perhalo-2-nitrobuta-1,3-dienes as Novel Xanthine Oxidase, Tyrosinase, Elastase, and Neuraminidase Inhibitors

Abstract

S-substituted perhalo-2-nitrobuta-1,3-dienes 3a, b were synthesized by the reaction of polyhalo-2-nitrobuta-1,3-dienes 1a, b with allyl mercaptan. 1-(2,3-Dibromopropanethio)-4-bromo-1,3,4-trichloro-2-nitrobuta-1,3-diene 4 was obtained from the addition of bromine to S-substituted polyhalo-2-nitrobuta-1,3-diene 3b in carbon tetrachloride. Sulfoxides 5a, b, and 6 were obtained from the reaction of thiosubstituted polyhalonitrobutadienes 3a, b, and 4 with m-CPBA in CHCl 3 . The structures of the new compounds were determined by spectroscopic data (FTIR, 1 H NMR, 13 C NMR, MS). These compounds exhibited antixanthine oxidase, antityrosinase, antielastase, and antineuraminidase activities.

Effects of ethylthiosulfanylate and chromium (VI) on the state of pro/antioxidant system in rat liver

“…It is known that compounds with sulfur atoms induce the process of lipid hydroperoxides decomposition into non-radical products [21]. Sulfur-containing compounds have the ability to inhibit the activity of the xanthine-xanthine oxidase system and attenuate ROS-induced lipids and proteins peroxidation [22]. Garlic organosulfur compounds also attenuate lipids peroxidation by inhibition of xanthine-xanthine oxidase-induced ROS generation [23].…”

Recent progress in chemical approaches for the development of novel neuraminidase inhibitors

“…Onul and co-workers 97 have reported the synthesis of S-substituted perhalo-2-nitrobuta-1,3-dienes (3a,b) from the reaction of allyl mercaptan with polyhalo-2-nitrobuta-1,3-dienes (1a,b). The addition of bromine to S-substituted polyhalo-2-nitrobuta-1,3-diene (3b) in CCl 4 yielded 1-(2,3-dibromopropanethio)-4-bromo-1,3,4-trichloro-2-nitrobuta-1,3-diene (4).…”

A New Tyrosinase Inhibitor from the Red Alga Symphyocladia latiuscula (Harvey) Yamada (Rhodomelaceae)

“…Lately, tyrosinase inhibitory potentials of phlorotannins from marine algae have emerged with great interest [27,28,29]. Similarly, due to various advantages of halogens in drug pharmacokinetics such as lipophilicity, cell membrane solubility, membrane binding, permeation, diffusion, and half-life, chemists are focusing on the synthesis of novel tyrosinase inhibitors, taking halogenation as a basic tool [30,31,32]. However, reports on natural halogenated compounds from marine sources are limited.…”