Discovery of Novel Sulfonamide‐Based 5‐Arylidenerhodanines as Effective Carbonic Anhydrase (II) Inhibitors: Microwave‐Assisted and Ultrasound‐Assisted One‐Pot Four‐Component Synthesis, Molecular Docking, and Anti‐CA II Screening Studies

Abstract

The synthesis of N‐substituted‐5‐arylidenerhodanines was carried out by the optimized one‐pot sequential four‐component procedure with the condensation between 4‐aminobenzenesulfonamide, suitable aldehyde, ethyl bromoacetate, and carbon disulfide. In addition to traditional method, microwave‐irradiated and ultrasound‐irradiated techniques were implemented in water at ambitious conditions, and the target compounds were obtained in high yields and purity without purification methods. The enzyme inhibition activity of newly synthesized compounds on carbonic anhydrase (II) was also evaluated. The reference inhibitor molecule was sulfanilamide, the IC50 value of which was 3.5 μM. It was also found that the IC50 values of all examined molecules were in nanomolar level and much smaller than those of sulfanilamide. The inhibition between 93.5 and 99.6% was observed in the presence of new compounds synthesized in the present study at the accessible maximum concentration in the reaction mixtures. 5j, among the tested compounds possessing the lowest IC50 value, was found to be the most potent carbonic anhydrase (II) inhibitor.

Development, synthesis and validation of improved c‐Myc/Max inhibitors

“…Then, triethylamine and corresponding aromatic aldehyde (4) was added to the reaction mixture and sonicated for 5 min in order to carry out the final step of intramolecular ring closure. Considering the optimization studies examining the effect of the base on the reaction and our groups' previous studies,22,23 it was achieved high reaction yields by using TEA in the range of 81%–94%. The structures of purified compounds were verified by FTIR, MALDI‐TOF/MS, 1 H‐NMR, and 13 C‐NMR spectroscopy (Supplementary File).…”

Chemistry of heterocycles as carbonic anhydrase inhibitors: A pathway to novel research in medicinal chemistry review

“…Synthesized compounds were also subjected to molecular docking studies and were docked into active site of hCA II. It was observed that compounds 1190g (Ar = 4-NO 2 ) and 1190j were found to have excellent binding energies of value −11.23 and −9.300 kcal/ mol and 1190j also formed bond hydrogen bond with Asn62 and Thr199 [197] (Scheme 181). benzaldehyde 1192 in presence of ethanol and KOH to afford chalcone derivative 1193(a-f) followed by treatment with hydrazine hydrate to obtain desired compounds 1194(a-f).…”

“…Synthesized compounds were also subjected to molecular docking studies and were docked into active site of hCA II. It was observed that compounds 1190g (Ar = 4‐NO 2 ) and 1190j were found to have excellent binding energies of value −11.23 and −9.300 kcal/mol and 1190j also formed bond hydrogen bond with Asn62 and Thr199 [ 197 ] (Scheme 181).…”

Antityrosinase Activities and in silico ADME Properties of Fluorine-containing 1,2,4-triazole-5-on Derivatives

“…To determine the K m , V max , K i values and inhibition type of the inhibitor compound with the smallest IC 50 between the studied inhibitor compounds; the Lineweaver-Burk curve was created by using two distinctive inhibitor concentrations (20 µM and 40 µM) at a substrate concentration ranging from 0.01-1.25 mM [16,18,19].…”