Synthesis of some novel N5‐sulfonylated and N1‐alkyated pyrazole derivatives and their antimicrobial activity in conjunction with molecular docking study

Abstract

Some novel N5‐sulfonylated 4 were synthesized via sulfonylation of 5‐amino‐1H‐pyrazole derivative 1 with arylsulfonyl chlorides. On the other hand, N1‐alkylated pyrazoles 7 and 10 were synthesized through alkylation of compound 1 with each of chloroacetamides and ethylchloroacetate under different conditions. Condensation of compounds 4 and 7 with different aromatic aldehydes furnished the corresponding arylidene derivatives. In spite of, condensation of 10 with aromatic aldehydes afforded the 2‐(5‐amino‐2‐aryl‐1H‐pyrazol‐1‐yl)acetic acid. The structure of the newly synthesized compounds was elucidated by elemental analyses and spectral data. Also, the suggested mechanisms for their formation were studied. Additionally, some selected new compounds were screened against antimicrobial activity. Compound 7c exhibited a higher activity against Candida albicans (inhibition zone diameter [IZD] = 31.3 ± 0.6 mm) than the standard antibiotic Nystatin (IZD = 21 ± 0.5 mm). Also, compound 7c showed minimum inhibitory concentration = 125 and 250 μg/mL against Klebsiella pneumonia and Staphylococcus aureus, respectively. Molecular docking study also was carried out for compound 7c.

Green synthesis: Antimicrobial activity of novel benzothiazole-bearing coumarin derivatives and their fluorescence properties

“…Warfarin, a coumarin analogue, is an anticoagulant and a vitamin K antagonist [10,11] and coumaphos is used as insecticide which kills insect and mites as shown in Figure 2 [12]. We recently published diverse synthetic approaches for the preparation of benzothiazole and coumarine derivatives using nitriles as starting materials [13,14].In light of these finding and as part of our program aimed at the preparation of possible antimetabolites [15][16][17][18][19][20], which showed biologically important antimetabolic agents in many biochemical reactions [21,22] and in accordance of these reports and based on our previous results in the preparation of biologically active heterocycles [23][24][25][26][27][28], the current study reports a new grindstone method synthesis of some novel benzothiazoles bearing a coumarin moiety 5a-f and investigate their antimicrobial activity as well as fluorescence properties.…”

Synthesis of Antimicrobial Benzimidazole–Pyrazole Compounds and Their Biological Activities

“…Additionally, benzimidazoles treat mitochondrial dysfunction in Alzheimer’s disease [ 22 ], possess neurotropic, psychoactive, analgesic effects [ 23 ], anticoagulant proprieties [ 24 ] and are efficient agents in Diabetes mellitus [ 25 ]. Additionally, pyrazole compounds possess a diversity of biological activities as analgesic [ 26 , 27 , 28 ], anticonvulsivant [ 29 , 30 ], antitumor [ 31 , 32 , 33 , 34 ], antidiabetic [ 35 , 36 ], antimicrobial [ 37 , 38 , 39 , 40 , 41 , 42 , 43 ], antipyretic [ 44 , 45 ], antiviral [ 46 , 47 ], antimalarial [ 48 , 49 ], local anesthetic [ 50 ] and so forth.…”

Synthesis, reactions, and antimicrobial activity of 2‐cyano‐N′‐(4‐(2‐oxo‐2‐phenylethoxy)benzylidene)acetohydrazide derivatives

“…In the view of these observations and as a part of our ongoing research program aimed to the synthesis of biologically active heterocycles, [ 24–35 ] we report herein the synthesis of some new heterocyclic compounds depending on 2‐cyano‐ N ′‐(4‐(2‐oxo‐2‐phenylethoxy)‐benzylidene)acetohydrazide 2 as a starting compound that underwent reactions with usual chemical reagents delivering various species of heterocyclic compounds besides that antimicrobial activity assessment has been performed for some selected compounds as a biological application.…”