Synthesis and antioxidant, antixanthine oxidase, and antielastase activities of novel N,S‐substituted polyhalogenated nitrobutadiene derivatives

Abstract

In this study, three substituted polyhalogenated nitrobutadiene derivatives were synthesized. Compound 1-[(2,3-dibromopropyl)sulfanyl]-1,3,4,4-tetrachloro-2-nitrobuta-1,3-diene (4) was synthesized before by our group. Compounds 8-{[1-[(2,3-dibromopropyl)sulfany]-3,4,4-trichloro-2-nitrobuta-1,3-butadien-1-yl}-1,4-dioxa-8-azaspiro[4.5]decane (5) and 1-[(2,3-dibromopropyl)sulfanyl]-3,4,4-trichloro-N-(4-methylpiperazin-1-yl)-2-nitrobuta-1,3-diene-1-amine (6) were synthesized in this work as original compounds. Xanthine oxidase, elastase inhibition abilities, and antioxidant activities were investigated in this work for compounds 4, 5, and 6. In this study, compounds 4, 5, and 6 exhibited antixanthine oxidase, antielastase, and antioxidant activities. Among the compounds screened, compound 4 exhibited xanthine oxidase and elastase inhibitor effect similar to the standard compound. Among the three tested compounds, compound 6 showed potent DPPH radical scavenging and reducing power activities. Therefore, these three compounds (4, 5, and 6) may be useful as an antixanthine oxidase, antielastase, and antioxidant agent in pharmaceutical and cosmetic industry.

Design, synthesis, pharmacological evaluation, and in silico studies of the activity of novel spiro pyrrolo[3,4-d]pyrimidine derivatives

“…68 Additionally, new cyclohexane fused spiroselenuranes showed potent antioxidant activity. 69 It has been reported that some azaspiro compounds had antioxidant and antielastase activity, 70 as it was found that human neutrophil elastase modulates cytokine and growth factor expression. The antiinflammatory activity of the newly synthesized compounds was also evaluated for COX-1/COX-2 inhibitory activities using an ovine COX-1/human recombinant COX-2 assay kit, and celecoxib was used as a reference standard drug as shown in Table 6.…”

Xanthine oxidase inhibitory activity of new pyrrole carboxamide derivatives: In vitro and in silico studies

“…The IC 50 for allopurinol was determined as 5.43 µM as a positive control. In a previous study, Onul et al determined that the IC 50 value range of N , S ‐substituted polyhalogenated nitrobutadiene derivatives was 69.24–4275.47 µM for XO inhibition. Zhang et al found the range from 6.7 to 45 µM for 17 compounds of benzonitrile derivatives as IC 50 value for XO inhibition.…”

“…The XO inhibitory activities of pyrrole carboxamide compounds (5a-h) are given in Table 2 as half maximal inhibitory micromolar SCHEME 1 Synthetic pathways for the preparation of pyrrole carboxamide derivatives Onul et al [19] determined that the IC 50 value range of N,S-substituted polyhalogenated nitrobutadiene derivatives was 69.24-4275.47 µM for XO inhibition. Zhang et al [20] found the range from 6.7 to 45 µM for 17 compounds of benzonitrile derivatives as IC 50 value for XO inhibition.…”

The protective effect of vitamin U on pentylenetetrazole‐induced brain damage in rats

“…There have been various substances recently synthesized and proven their sulfur moiety effect. Onul et al [ 70 ] reported the importance of sulfur‐containing polyhalogenated nitrobutane derivatives and the inhibitory power of these newly synthesized substances on XO. In addition to that Özerkan et al [ 71 ] reported new palladium complexes designed with sulfur ingredients and they proved that the power of sulfur moiety is more active when bounded alkyl group number is less.…”