Synthesis, antioxidant and carbonic anhydrase I and II inhibitory activities of novel sulphonamide-substituted coumarylthiazole derivatives

Kurt, Belma Zengin; Sönmez, Fatih; Bilen, Çiğdem; Ergün, Adem; Gençer, Nahit; Arslan, Oktay; Küçükislamoğlu, Mustafa

doi:10.3109/14756366.2015.1077823

Cited by 28 publications

(17 citation statements)

References 57 publications

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“…The inhibition values of them ranged from low micromolar to nanomolar. These compounds have stronger inhibitory effect than the synthesized tetrahydroquinoline containing urea moiety in this study; however, 7 k (IC 50 =5.28 μM and 5.51 μM, for hCA I and hCA II, respectively) showed higher inhibitory properties against hCA I and II compared to some urea, sulfonamide and coumarin derivatives, reported in our previously works with an IC 50 value of between 6.79 μM and 620 μM, for hCA I; between 6.54 μM and 51.45 μM, for hCA II.…”

Section: Resultscontrasting

confidence: 44%

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Synthesis, Biological Activity and Structure‐Activity Relationship of Novel Diphenylurea Derivatives Containing Tetrahydroquinoline as Carbonic Anhydrase I and II Inhibitors

et al. 2018

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A series of novel tetrahydroquinoline derivatives containing urea moiety was synthesized and their in vitro inhibitory effects on the human carbonic anhydrase isoenzymes (hCA−I and hCA‐II) were evaluated by using the CO2 hydration method. All the synthesized compounds exhibited inhibitory activity against both hCA I and hCA II with 1‐(4‐fluorophenyl)‐3‐(4‐(4‐p‐tolyl‐5,6,7,8‐tetrahydroquinolin‐2‐yl)phenyl)urea (7 k, IC50 value of 5.28 μM and 5.51 μM, against hCA I and hCA II, respectively) as the strongest inhibitor in this study. Structure‐activity relationships were also investigated. The results showed that most of synthesized compounds have a higher inhibitory activity against hCA I than hCA II. Also the substituents, containing two or more pairs of non‐bonding electrons, generally increased the hCA I and II inhibitory activity. Furthermore, some electronic parameters such as the highest occupied molecular orbital and the lowest unoccupied molecular orbital (HOMO‐LUMO) energy levels, electron affinity, total energy and dipole moments of the best inhibitors (7 b, 7 h and 7 k) in this study were also calculated by using Gaussian software. The results revealed that HOMO‐LUMO energy differences, total energy, chemical hardness and dipole moment of 7 b, 7 h and 7 k showed a linear relationship with increasing inhibitory activity.

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Section: Resultscontrasting

confidence: 44%

“…In the light of these facts, and as a continuation of our previous studies, the present work reports here the synthesis of new tetrahydroquinoline containing diphenylurea ( 7 a‐t ) derivatives and their inhibitory effects on human carbonic anhydrase I and II (hCA I and hCA II). Structure‐activity relationships were also investigated.…”

Section: Introductionmentioning

confidence: 77%

Synthesis, Biological Activity and Structure‐Activity Relationship of Novel Diphenylurea Derivatives Containing Tetrahydroquinoline as Carbonic Anhydrase I and II Inhibitors

et al. 2018

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“…Among the aforementioned scaffolds, coumarin and thiazole have gained much attention in recent decades in the field of medicinal chemistry as leading pharmacophores with a wide range of pharmacological activities. Some of the biological properties include antioxidant, anticholinesterase activity (AChE and BuChE), carbonic anhydrase I, II, and IX inhibiting activities and aflatoxigenic activity …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, In Vitro Evaluation and Docking Studies of Pyrazole‐Thiazole Hybrids as Antimicrobial and Antibiofilm Agents

et al. 2018

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In the present study, a series of novel pyrazole‐thiazole hybrids (4a‐l) were designed, synthesized and assessed for their in vitro antimicrobial activity against both Gram‐positive and Gram‐negative pathogenic bacterial and fungal strains. Compounds derived from p‐CH3 phenyl (4b), p‐Br phenyl (4g), 8‐bromocoumarinyl (4k), and 6,8‐dibromocoumarinyl (4l) exhibited promising inhibitory activity against the tested bacterial strains with minimum inhibitory concentration (MIC)/minimum bactericidal concentration (MBC) spectrum of 1.9/7.8 μg/mL to 3.9/7.8 μg/mL. The compounds with p‐CH3 phenyl (4b), p‐OCH3 phenyl (4c), benzo[f]coumarinyl (4j), 8‐bromocoumarinyl (4k) substitutions showed their inhibitory potency against various Candida strains with MIC/minimum fungicidal concentration (MFC) values of 3.9/7.8 μg/mL. Also, anti‐biofilm and toxicity profile of the compounds was also tested. The biofilm inhibition results revealed that the compound 4 j exhibited promising activity with an IC50 value of 11.8 μM against S. aureus MTCC 96, while 4 k showed significant activity against S. aureus MLS16 MTCC 2940, K. planticola MTCC 530 and C. albicans MTCC 3017 with IC50 values of 12, 14 and 16 μM, respectively. The present study has emphasized that thiazole‐pyrazole hybrids with benzothiazole and coumarin scaffolds can be a novel and potent class of molecules with potential biological activities.

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“…The antioxidant activity was determined by using ABTS .+ method . This method is based on the ability of hydrogen or electron‐donating antioxidants to decolorize the performed radical monocation of 2,2′‐azino‐bis(3‐ethylbenzthiazoline‐6‐sulfonic acid) generated due to oxidation of ABTS with potassium persulfate.…”

Section: Biological Activitiesmentioning

confidence: 99%

Synthesis, Anticholinesterase, Antioxidant, and Anti‐Aflatoxigenic Activity of Novel Coumarin Carbamate Derivatives

et al. 2018

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New coumarin derivatives with the carbamate moiety were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. 4methyl-2-oxo-2H-chromen-7-yl cycloheptylcarbamate (4 h) showed the strongest inhibition against AChE with IC 50 values of 2.30 mM, and 2-oxo-2H-chromen-7-yl-(cyclohexylmethyl) carbamate (4 c) and 4-methyl-2-oxo-2H-chromen-7-yl-(cyclohexylmethyl)carbamate (4 g) were found to be the most potent BuChE inhibitors with IC 50 value of 0.003 mM and 0.004 mM, respectively. Moreover antioxidant, anti-aflatoxigenic activities, protective effects against aflatoxin-B1 (AFB1) in H4IIEÀC3 cells and effects on glutathione s-transferase of the synthesized compounds were investigated. The synthesized coumarin carbamates inhibited AFB1 in H4IIEÀC3 cells. Western blot analyses confirmed that GSTa protein was induced in cells treated with coumarin carbamates and AFB1. These results showed that the synthesized coumarin carbamates possess a potent protective effect against AFB1.[a] Dr.

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Synthesis, antioxidant and carbonic anhydrase I and II inhibitory activities of novel sulphonamide-substituted coumarylthiazole derivatives

Cited by 28 publications

References 57 publications

Synthesis, Biological Activity and Structure‐Activity Relationship of Novel Diphenylurea Derivatives Containing Tetrahydroquinoline as Carbonic Anhydrase I and II Inhibitors

Synthesis, Biological Activity and Structure‐Activity Relationship of Novel Diphenylurea Derivatives Containing Tetrahydroquinoline as Carbonic Anhydrase I and II Inhibitors

Design, Synthesis, In Vitro Evaluation and Docking Studies of Pyrazole‐Thiazole Hybrids as Antimicrobial and Antibiofilm Agents

Synthesis, Anticholinesterase, Antioxidant, and Anti‐Aflatoxigenic Activity of Novel Coumarin Carbamate Derivatives

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