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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
Author(s) -
Mermer Arif,
Demirbas Neslihan,
Cakmak Ummuhan,
Colak Ahmet,
Demirbas Ahmet,
Alagumuthu Manikandan,
Arumugam Sivakumar
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3635
Subject(s) - chemistry , carbonic anhydrase , sulfanilamide , sulfonamide , molecule , aldehyde , microwave irradiation , enzyme , combinatorial chemistry , ethyl bromoacetate , carbonic anhydrase ii , organic chemistry , stereochemistry , biochemistry , catalysis
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 IC 50 value of which was 3.5 μ M . It was also found that the IC 50 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 IC 50 value, was found to be the most potent carbonic anhydrase (II) inhibitor.