In vitro inhibition effects on erythrocyte carbonic anhydrase I and II and structure-activity relationships of cumarylthiazole derivatives

Kurt, Belma Zengin; Sönmez, Fatih; Gökçe, Başak; Ergün, Adem; Gençer, Nahit; Demir, Taki; Arslan, Oktay; Küçükislamoğlu, Mustafa

doi:10.1134/s1068162016050046

Cited by 16 publications

(9 citation statements)

References 37 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 SAR studies revealed that substitution on C-3 of the uracil ring with a methyl group increased inhibitory action towards human carbonic anhydrase I and II. Further, the most active compound 62 showed hCA I inhibition with IC 50 = 6.79 μm (Kurt et al, 2016).…”

Section: Miscellaneous Activitymentioning

confidence: 94%

An overview on synthetic and pharmaceutical prospective of pyrido[2,3‐d]pyrimidines scaffold

Yadav

Shah

2020

Chem Biol Drug Des

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Pyrido[2,3-d]pyrimidine, a fused hetero-bicyclic nucleus containing pyridine and pyrimidine rings has attained the momentary attention in the sphere of multicomponent synthetic protocol and medicinal chemist. Pyrido[2,3-d]pyrimidine derived drugs have manifested diverse pharmacological activities, particularly, anti-inflammatory, cytotoxic, antimicrobial, phosphodiesterase inhibitors and cytokine inhibitors etc. The present review illustrates various modern synthetic strategies adopted, the structure-activity relationship (SAR) aspects and discloses the extensive crucial biological properties (anticancer, anti-infectious, anti-diabetics and CNS agents) of pyrido[2,3-d]pyrimidines. K E Y W O R D S anticancer, anti-diabetics, anti-infectious, CNS agents, pyrido[2,3-d]pyrimidines How to cite this article: Yadav P, Shah K. An overview on synthetic and pharmaceutical prospective of pyrido[2,3-d]pyrimidines scaffold.

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In vitro inhibition effects on erythrocyte carbonic anhydrase I and II and structure-activity relationships of cumarylthiazole derivatives

Cited by 16 publications

References 37 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

An overview on synthetic and pharmaceutical prospective of pyrido[2,3‐d]pyrimidines scaffold

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