Synthesis, Antibacterial and Insecticidal Activities of Novel Capsaicin Derivatives Containing a Sulfonic Acid Esters Moiety

Abstract

In order to develop an efficient and broad-spectrum bactericide, a series of novel capsaicin derivatives containing a sulfonic acid esters moiety was synthesized. The structure of these compounds were confirmed by nuclear magnetic resonance spectroscopy (NMR) and high-resolution mass spectrum (HRMS). The results of the bioactivities revealed that some target compounds exhibited remarkable antibacterial activity. Compound 3b exhibited the highest activities against Pseudomonas syringae pv. actinidiae (Psa), Xanthomonas oryzae pv. oryzae (Xoo), and Xanthomonas axonopodis pv. citri (Xac), and the values were 86, 54, and 92% at 50 μg/ml, respectively, which were higher than were for thiodiazole copper (87, 34, and 77%) and bismerthiazol (87, 37 and 75%). Although some compounds also showed certain activity against Spodoptera frugiperda, it was weaker than the positive controls monosultap and mulfoxaflor. Thus, the bioassay results recommend that these newly designed and synthesized scaffolds should be used as a bactericide lead compound rather than an insecticide lead compound.

In Vitro and in Silico Studies of 3‐Hydroxyflavone‐Based Sulfonate Esters: Potent Acetylcholinesterase, Carbonic Anhydrase and α‐Glycosidase Inhibitors

“…Sulfonate esters appear as suitable starting compounds in the activation of the hydroxy group, [23,24] in many coupling reactions, [25][26][27] in the production of sulfonamides [27][28][29][30] which are synthetic antibiotics used as antibacterial agents. Along with this versatile use, it is of great interest to researchers to develop many new methods for the production of sulfonate esters, [21,28,[35][36][37][38][39] which possess important biological activity such as anticancer, [19,40] antibacterial, [18,35,41] some enzyme inhibitory, [20,42,43] anti-viral, [21] insecticidal activities. [22] Along with all these, the possible DNA effects of sulfonate esters should not be ignored.…”

“…[17] In the recent year, the synthesis of some sulfonate ester derivatives has gained significant attention from researchers. This class of molecules has quickly become prominent in the field due to their importantant biological activity, [18][19][20][21][22] as presented in Figure 2.…”

Electro-induced O–S bonding reaction targeting biological macromolecules

“…These compounds exhibit remarkable properties relevant to pesticides and medicinal agents, serving as versatile intermediates in chemical transformations. 21,22 Traditional synthetic routes for sulfonyl esters typically involve the reaction of sulfonyl chlorides or sulfonamides with alcohols or ketones in the presence of amines as bases. [23][24][25][26] However, sulfonyl chlorides are highly reactive and pose challenges in terms of storage and handling.…”

Synthesis and Antibacterial Activity of Some Aryloxyacetic Acid Derivatives Containing Aryl Sulfonate Moiety

“…10 Besides, sulfonate moiety is known to possess several antimicrobial activities. [11][12][13][14] Because a new series of 4-((2-(2-(aryloxy)acetyl) hydrazineylidene)methyl)phenyl 4-methyl benzene-sulfonate and 2-methoxy-4-((2-(2-(aryloxy)acetyl) hydrazineylidene)methyl)phenyl 4-methyl benzenesulfonate was designed and synthesised as potential antibacterial agents. Thus, we aim to discover new compounds with high antibacterial activity by combining sulfonate and hydrazone groups, each with an antimicrobial effect.…”