Synthesis and Antioxidant Activity of New Neomenthyl and Caranyl Thiotriazoles

Synthesis and Antioxidant Activity of Carane and Pinane Based Sulfenimines and Sulfinimines

“…Antioxidant activity (AOA) of compounds 3a-5a, 4b, 5b, (S)-3a-(S)-5a, (R)-3a-(R)-5a, (S)-4b, (S)-5b, (R)-4b and (R)-5b was evaluated in the cellular (red blood cells) and non-cellular (lipid-containing brain homogenate) model systems that we used earlier in the study of the neomenthane and isobornane sulfenimines, [6] as well as cis-and trans-myrtanylthiotriazoles, caranylthiotriazoles, and neomenthylthiotriazoles. [7,8] In non-cellular model system, the highest antioxidant activity has been shown by derivatives with the p-nitrobenzylidene moiety (carane sulfinimines (S)-4a and (R)-4a, pinane sulfenimine 4b and sulfinimines (S)-4b, (R)-4b), as well as pinane sulfenimine 5b with 2hydroxybenzylidene moiety at both concentrations (100 μM and 1 mM) ( Figure 3). The lowest antioxidant activity was exhibited by the carane 4-fluorobenzylidene derivatives 3a, (S)-3a, (R)-3a and 2-hydroxybenzylidene sulfinimines (S)-5a, (R)-5a.…”

“…Antioxidant activity (AOA) of compounds 3a – 5a , 4b , 5b , ( S )‐ 3a –( S )‐ 5a , ( R )‐ 3a –( R )‐ 5a , ( S )‐ 4b , ( S )‐ 5b , ( R )‐ 4b and ( R )‐ 5b was evaluated in the cellular (red blood cells) and non‐cellular (lipid‐containing brain homogenate) model systems that we used earlier in the study of the neomenthane and isobornane sulfenimines, as well as cis ‐ and trans ‐myrtanylthiotriazoles, caranylthiotriazoles, and neomenthylthiotriazoles …”

“…Antioxidant and membrane‐protective activity of cis ‐ and trans ‐myrtanylthiotriazoles was revealed . In article, it was shown that neomenthylthiotriazoles outperform the antioxidant activity of isobornylthiotriazoles. Novel carane and pinane based sulfenimines and sulfinimines were synthesized to reveal the impact of the terpene framework and the influence of the sulfinyl group and the substituent in the benzylidene moiety on the antioxidant activity.…”

Synthesis of Chiral CF3‐Contaning Pinane‐Type Hydroxythiols

“…Sulfur‐containing monoterpenoids have a wide spectrum of biological activity. It is known that such compounds exhibit antifungal, [1] anti‐inflammatory, anti‐ulcer, [2] anti‐helicobacter, antitumor, antiparasitic activity, [3] and also have membrane‐protective, antioxidant, [4–9] antiplatelet, [10,11] antimicrobial properties [12,13] . The biological activity of these compounds also depends on the oxidation state of the sulfur atom [14] .…”

“…Terpene thiols can be used as intermediates in organic synthesis to produce sulfochlorides, [15–17] sulfonamides, [18] sulfides, [4,8,9,19] disulfides, [5,20] sulfenimines and sulfinimines [7,21–25] . Chiral monoterpene hydroxythiols can also be used as chiral ligands or organocatalysts in asymmetric catalysis and as chiral auxiliaries in asymmetric synthesis [26–36] .…”