Rapid Synthesis of N‐Tosylhydrazones under Solvent‐Free Conditions and Their Potential Application Against Human Triple‐Negative Breast Cancer

Abstract

Some N‐tosylhydrazone derivatives were effectively synthesized under solvent‐free conditions by using a grinding method at room temperature. The short reaction time, clean and mild process with simple workup and easy purification of the target compounds were salient features of the present protocol, which enables straightforward access to N‐tosylhydrazones. Among the tosylhydrazone derivatives evaluated, compound 3 l exhibits excellent apoptosis‐promoting and anticancer potential against triple‐negative breast cancer (TNBC) cell lines. This research shows that our synthesized compound 3 l may be a desirable and effective therapeutic drug against TNBC.

Coupling of N‐Tosylhydrazones with Tetrazoles: A Regioselective Synthesis of 2,5‐Disubstituted‐2H‐Tetrazoles

“…To broaden the scope of substrates, we further investigated the reaction with substituted benzaldehyde tosylhydrazones 1 b – j and 2‐phenylacetaldehyde tosylhydrazone 1 k with 5‐phenyltetrazole (Table 3). To this end the necessary N ‐tosylhydrazones 1 were synthesized with classical solution chemistry [28] and/or with a mechanochemical process [29] (see Supporting information for details). These couplings were found to be somehow affected by the substituents.…”

“…Finally, the scope of the reactions of ketone tosylhydrazones 8 (prepared by solution reactions [28] and/or with a mechanochemical method [29] (see Supporting information for details)) with tetrazoles 2 was studied and results are listed in Table 6. It seems obvious from the outcome of the couplings that ketone tosylhydrazones 8 react less smoothly than aldehyde tosylhydrazones 1 , require longer reaction time and result in lower yields.…”

N–H Insertion of Anilines on N-Tosylhydrazones Induced by Visible Light Irradiation

“…Aspect: white solid. 1 29 4 -M e t h y l -N ′ -( 1 -( p y r i d i n e -3 -y l ) e t h y l i d e n e )benzenesulfonohydrazide (1f) was obtained according to general procedure A from 1-(pyridin-3-yl)ethan-1-one and p-toluenesulfonohydrazide. Aspect: yellow solid.…”

Synthesis of Arylsulfonyl Hydrazone Derivatives: Antioxidant Activity, Acetylcholinesterase Inhibition Properties, and Molecular Docking Study

“…[1][2] The pharmacological properties of benzene sulfonyl hydrazones, such as enzymatic modulation, [3][4] analgesia, [5] and antifungal [6] and antibacterial potential [7][8][9][10][11][12] are mainly well recognized. Besides that, it also contains a broad spectrum of bioactivity such as anticancer 1-3, [13][14][15][16][17][18][19][20][21] antidepressant properties [22][23] and activity against Alzheimer's disease [24][25][26] (Figure 1).…”