Syringaldehyde as a scaffold for the synthesis of some biologically potent heterocycles

Abstract

Syringaldehyde was utilized in synthesis of different heterocyclic systems. Some of the synthesized compounds 2, 7, 8, 10, 11, and 13 were tested for antioxidant activity where they showed ability to inhibit oxidation in kidney and rat brain homogenates using 2, 2′‐azinobis (3‐ethylbenzothiazoline‐6‐sulfonic acid) (ABTS). Also, the activity against cancer was examined using the standard MTT method for two human tumor cell lines namely; mammary gland breast cancer MCF‐7 and hepatocellular carcinoma HepG2. The highest activity as antioxidant and antitumor agents was exhibited by compounds 8 and 11. However, moderate activities were shown by compounds 10 and 13. While, compounds 2, 7 showed weak activities.

Design, synthesis, anticancer, and docking of some S‐ and/or N‐heterocyclic derivatives as VEGFR‐2 inhibitors

“…The formation of pyrazole derivative 7 is believed to proceed through the Michael addition of hydrazine hydrate to α,β‐unsaturated nitrile 6 and in situ auto‐oxidation to yield the target compound 7 according to the reported procedure. [ 39 ]…”

“…The formation of pyrazole derivative 7 is believed to proceed through the Michael addition of hydrazine hydrate to α,β-unsaturated nitrile 6 and in situ auto-oxidation to yield the target compound 7 according to the reported procedure. [39] Equimolar amounts of 3 and phenyl isothiocyanate [40] were heated under reflux while stirring in dimethylformamide (DMF) in the presence of a catalytic amount of potassium hydroxide to afford azete derivative 8 as shown in (Scheme 3). On the contrary, at room temperature, the same reaction allowed the active methylene of Furthermore, the reaction of 9 under similar conditions with ethyl chloroacetate afforded thiazolidinone derivative 13 (Scheme 3).…”

Separation and Purification of Vanillin and Syringaldehyde from an Oxidized Kraft Liquor – A Mini Review

“…Vanillin acid [46,48] Syringic acid [46] mediate of the antibacterial drugs trimethoprim, bactrim, and biseptol [59].…”

“…However, syringaldehyde has the advantage of having two methoxyl groups, whereas vanillin has only one, making syringaldehyde less reactive. Although less commercialized than vanillin, the chemistry and manipulation of syringaldehyde is growing rapidly, especially after the discovery of its role as an essential intermediate of the antibacterial drugs trimethoprim, bactrim, and biseptol 59.…”

Laccase-catalyzed derivatization of 6-aminopenicillanic, 7-aminocephalosporanic and 7-aminodesacetoxycephalosporanic acid

“…A further advantage is the specificity of the laccase-initiated reaction, which catalyse the amination and thiolation of para - and ortho -dihydroxylated aromatic compounds (Abdel-Mohsen et al 2014 ; Manda et al 2005 ; Niedermeyer et al 2005 ; Patel and Gupte 2018 ; Schlippert et al 2016 ; Wellington et al 2013 ). Further examples of useful modifications are laccase-mediated reactions in which two antibiotics containing a phenol moiety are combined (Agematu et al 1993 ), or where a phenolic compound is added into an antibiotic containing a phenolic moiety (Anyanwutaku et al 1994 ), or the synthesis or transformation of heterocyclic compounds (Mikolasch and Schauer 2003 ; Saadati et al 2018 ; Schäfer et al 2001 ; Youssef et al 2020 ).…”