Synthesis and biological activity of fluorine-containing amino derivatives based on 4-caranethiol

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

“…The carane sulfinimines ( S )‐ 3a and ( R )‐ 3b were isolated in pure form and characterized. The spectral data of sulfinimines are similar to those described in article . The mixtures of diastereoisomeric sulfinimines ( S )‐ 4b , ( R )‐ 4b and ( S )‐ 5b , ( R )‐ 5b were found not to be separable by column chromatography (CC).…”

“…Some of the previously described carane sulfenimines 4a , 5a and sulfinimines ( S )‐ 4a , ( R )‐ 4a , ( S )‐ 5a , ( R )‐ 5a have been found to reveal antimicrobial properties combined with low acute toxicity to human embryonic kidney cells HEK‐293 . Within the framework of this study, carane sulfenimine 3a and diastereoisomeric sulfinimines ( S )‐ 3a and ( S )‐ 3a containing 4‐fluorobenzylidene substituent were synthesized using the same procedure to compare them with salicylic and 4‐nitrobenzylidene derivatives.…”

“…Some of the previously described carane sulfenimines 4a, 5a and sulfinimines (S)-4a, (R)-4a, (S)-5a, (R)-5a have been found to reveal antimicrobial properties combined with low acute toxicity to human embryonic kidney cells HEK-293. [9] Within the framework of this study, carane sulfenimine 3a and diastereoisomeric sulfinimines (S)-3a and (S)-3a containing 4-fluorobenzylidene substituent were synthesized using the same procedure to compare them with salicylic and 4nitrobenzylidene derivatives. It is known that the introduction of fluorine into a drug molecule can noticeably affect the binding to the corresponding receptors, the permeability of membranes, and it also can modify the metabolic pathways and pharmacokinetic properties.…”

“…The spectral data of sulfinimines are similar to those described in article. [9] The mixtures of diastereoisomeric sulfinimines (S)-4b, (R)-4b and (S)-5b, (R)-5b were found not to be separable by column chromatography (CC).…”

“…Novel pinane sulfenimines 4b , 5b and sulfinimines ( S )‐ 4b , ( R )‐ 4b , ( S )‐ 5b , ( R )‐ 5b were synthesized on the basis of 10‐hydroxyisopinocamphylthiol 1b . In the first stage, thiol 1b was treated by N ‐chlorosuccinimide (NCS) in liquid ammonia using a familiar procedure with the formation of unstable sulfenamide 2b , which further formed the sulfenimines 4b and 5b in 81–98 % yields in an in situ condensation reaction with 4‐nitrobenzaldehyde and salicylic aldehyde ( Scheme ). IR Spectra of sulfenimines 4b and 5b contain absorption bands typical for the C=N bond at 1595–1616 cm −1 .…”