Synthesis and Antinociceptive Profile of Novel Acidic Sulphonylhydrazone Derivatives From Natural Safrole

Abstract

The synthesis and antinociceptive activity of new sulphonylhydrazone derivatives is described. The synthetic route started from safrole, an abundant Brazilian natural product which occurs in sassafras oil (Ocotea pretiosa). The active compounds were obtained by introducing an acidic moiety in the phenyl ring of the sulphonylhydrazone framework. The compounds were tested for analgesic and anti‐inflammatory activity in the acetic acidinduced abdominal constriction and carrageenan‐induced rat paw oedema tests, respectively. The most active analgesic was (4′‐carboxybenzylidene) 6‐methyl‐3,4‐methylene‐dioxyphenylsulphonylhydrazide which was approximately 1.5‐fold more potent than the standard dipyrone (52.4 vs 35.9% inhibition, respectively). The most active anti‐inflammatory was the phenol compound (4′‐hydroxy‐3,5‐ditert‐butylbenzylidene) 6‐methyl‐3,4‐methylenedioxyphenylsulphonylhydrazide (30% inhibition). The introduction of an acidic substituent in the phenyl ring of the sulphonylhydrazone moiety led to new lead compounds from safrole with analgesic and anti‐inflammatory activity.

Synthesis, characterization and antimicrobial activity of salicylaldehyde benzenesulfonylhydrazone (Hsalbsmh)and its Nickel(II), Palladium(II), Platinum(II), Copper(II), Cobalt(II) complexes

“…Imidosulfonylhydrazones have antibacterial and antinociceptive properties [21]. Acidic sulfonyl hydrazone derivatives have analgesic and anti-inflammatory properties [22]. Benzaldehyde arylsulfonylhydrazones possess antineoplastic activity against human stomach cancer SGC 7901 cells [23].…”

Synthesis and characterization of chloromaleimidobenzenesulfonylhydrazones

“…The antineoplastic activity of some sulfonylhydrazones has also been reported 6 . Studies carried out by Barreiro et al have shown that sulfonylhydrazone derivatives of safrole have potent analgesic action, exceeding and/or equalling the potency observed under the same conditions for either dypirone or indomethacin 7 . This paper describes the synthesis of chloromaleimidobenzenesulfonylhydrazones, in a search for antibactericidal and/or antinociceptive lead compounds.…”

Methyl Effect on the Metabolism, Chemical Stability, and Permeability Profile of Bioactive N-Sulfonylhydrazones

“…Sulfonylhydrazones (SH) are organic compounds described as nonclassical isosteres of acylhydrazones (NA) and considered as privileged structures. − The synthesis and applications of SH are widely explored in medicinal chemistry due to their different biological and pharmacological properties, such as antinociceptive, − antiasthmatic, antioxidant, antibacterial, , antidepressant, antineoplastic, − and antidiabetic …”