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Journal of Chemistry
Volume 2018, Article ID 4386031, 11 pages
https://doi.org/10.1155/2018/4386031
Research Article

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

1Organic Chemistry Division, Department of Chemistry, Faculty of Engineering, Istanbul University, Avcilar, 34320 Istanbul, Turkey
2Biochemistry Division, Department of Chemistry, Faculty of Engineering, Istanbul University, Avcilar, 34320 Istanbul, Turkey

Correspondence should be addressed to Nihal Onul; rt.ude.lubnatsi@mliy

Received 7 August 2017; Revised 13 November 2017; Accepted 27 November 2017; Published 31 January 2018

Academic Editor: Xinyong Liu

Copyright © 2018 Nihal Onul et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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 CHCl3. The structures of the new compounds were determined by spectroscopic data (FTIR, 1H NMR, 13C NMR, MS). These compounds exhibited antixanthine oxidase, antityrosinase, antielastase, and antineuraminidase activities.