52494-15-2Relevant academic research and scientific papers
Potential inhibitors of human carbonic anhydrase isozymes I and II: Design, synthesis and docking studies of new 1,3,4-thiadiazole derivatives
Alt?ntop, Mehlika Dilek,Sever, Belgin,?zdemir, Ahmet,Kucukoglu, Kaan,Onem, Hicran,Nadaroglu, Hayrunnisa,Kaplanc?kl?, Zafer As?m
, p. 3547 - 3554 (2017/05/29)
In the last years, inhibition of carbonic anhydrase (CA) has emerged as a promising approach for pharmacologic intervention in a variety of disorders such as glaucoma, epilepsy, obesity, and cancer. As a consequence, the design of CA inhibitors (CAIs) is a highly dynamic field of medicinal chemistry. Due to the therapeutic potential of thiadiazoles as CAIs, new 1,3,4-thiadiazole derivatives were synthesized and investigated for their inhibitory effects on hCA I and hCA II. Although the tested compounds did not carry a sulfonamide group, an important pharmacophore for CA inhibitory activity, it was a remarkable finding that most of them were more effective on hCAs than acetazolamide (AAZ), the reference agent. Among these compounds, N′-((5-(4-chlorophenyl)furan-2-yl)methylene)-2-((5-(phenylamino)-1,3,4-thiadiazol-2-yl)thio)acetohydrazide (3) was found to be the most effective compound on hCA I with an IC50 value of 0.14?nM, whereas N′-((5-(2-chlorophenyl)furan-2-yl)methylene)-2-((5-(phenylamino)-1,3,4-thiadiazol-2-yl)thio)acetohydrazide (1) was found to be the most potent compound on hCA II with an IC50 value of 0.15?nM. According to molecular docking studies, all compounds exhibited high affinity and good amino acid interactions similar to AAZ on the both active sites of hCA I and hCA II enzymes.
Synthesis and in vitro evaluation of thiadiazole derivatives as AChE, Bu-ChE and LOX inhibitors
Altintop, Mehlika Dilek,?zdemir, Ahmet,Abu Mohsen, Usama,Temel, Halide Edip,Akal, Gül?en,Kaplancikli, Zafer Asim
, p. 1062 - 1069 (2015/04/14)
N'-Benzylidene-2-[[5-(phenylamino)-1,3,4-thiadiazol-2-yl]thio]acetohydrazide derivatives (5a-p) were synthesized to screen for their AChE, BuChE and LOX inhibitory activity. The CCK-8 assay was also carried out to determine their cytotoxicity against NIH/3T3 cells. The most potent AChE inhibitors were found as compounds 5m (49.79% ± 3.08) and 5p (42.39% ± 3.19), whereas the most potent BuChE inhibitor was found as compound 5d (35.15% ± 2.21). Among these derivatives, N'-(3-methoxybenzylidene)-2-[[5-(phenylamino)-1,3,4-thiadiazol-2-yl]thio]acetohydrazide (5p) can be considered as the most promising AChE inhibitor due to its low cytotoxicity to NIH/3T3 cells (IC50 > 500 μg/mL). N'-(4-Methoxybenzylidene)-2-[[5-(phenylamino)-1,3,4-thiadiazol-2-yl]thio]a-cetohydrazide (5n) exhibited weak inhibition on LOX (%20.65 ± 0.08), whilst the other compounds were not active.
Synthesis of 3-(thiadiazol-2-ylthio-, pyridin-2-ylthio- and benzimidazol-2-ylthio)-2H-1-benzopyran-2-ones
Ahluwalia, V K,Tyagi, Renu,Khurana, Anju
, p. 1097 - 1100 (2007/10/02)
The title compounds have been prepared by the reaction of thiadiazol-2-ylthio-, pyridin-2-ylthio- and benzimidazol-2-ylthioacetic acid hydrazides with o-hydroxybenzaldehydes followed by cyclization of the resultant acetylhydrazones in the presence of PPA.
