Sulfur-Containing Pyrazoles, Pyrazolines and Indazoles

Revisiting the Chemistry of Vinylpyrazoles: Properties, Synthesis, and Reactivity

“…Pyrazoles containing sulfur atoms have interesting biological activities and are used as drugs [ 75 ]. This type of pyrazoles can be prepared from vinylpyrazoles and their alkyl derivatives, which are known to react with thiols via either ionic or free radical mechanisms, with the formation of α- and β-addition products, depending on whether the addition follows the Markovnikov rule or not, respectively [ 76 ].…”

DOS strategy, crystal structure, and in silico evaluation of the anti‐inflammatory activity of hydroxysulfanylazole derivatives

“…Similarly, the С…О distances in the С-Н…О hydrogen bonds in 7a and 7d differ insignificantly (3.547 and 3.530 Å, respectively). Note that classical N-H… O and O-H…N hydrogen bonds in molecules 7a and 7d give rise to С(5) chains along the с axis, while those in molecules 3 form cyclic tetramers R 4 4 10 ð Þ: In the crystals of 7f, the molecules are stacked along the b axis, unlike those in 7a or 7d; this is probably due to the large size of the 1,3-benzodioxole substituent in comparison with the phenyl and 4-fluorophenyl groups.…”

“…The interest in the azole heterocycles with sulfur‐containing substituents is justified. [ 4 ] Currently, there is an extensive series of S‐derivatives of pyrazole and isoxazole that are available in the pharmaceutical market as drug dosage forms, for example, metamizole sodium (Analgin) (non‐selective COX‐1 and COX‐2 inhibitors), celecoxib, valdecoxib (selective COX‐2 inhibitors), and mofezolac (selective COX‐1 inhibitors). Mention should also be made of the potential anti‐inflammatory agents based on amino and sulfanyl phenazone (3H‐pyrazol‐3‐one) derivatives, which are prepared by the metal‐free aminomethylation reaction of 4‐aminoantipyrine with formaldehyde and thiols involving the NH 2 group [ 5 ] and by indium(III)‐catalyzed thiomethylation of the С4‐Н position of antipyrine with formaldehyde and thiols (Figure 1b).…”