Investigation of 3-sulfamoyl coumarins against cancer-related IX and XII isoforms of human carbonic anhydrase as well as cancer cells leads to the discovery of 2-oxo-2H-benzo[h]chromene-3-sulfonamide – A new caspase-activating proapoptotic agent

Dar’in, Dmitry; Kantin, Grigory; Kalinin, Stanislav; Sharonova, Tatiana; Bunev, Alexander S.; Ostapenko, Gennady I.; Nocentini, Alessio; Sharoyko, Vladimir V.; Krasavin, Mikhail

doi:10.1016/j.ejmech.2021.113589

Cited by 18 publications

(13 citation statements)

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“…Dar’in et al in 2021 synthesized series of seventeen 3-sulfonamide substituted coumarin scaffolds via the reaction of ethyl 2-sulfamoylacetate 45 and various substituted salicylaldehydes 44 in n-butanol at 110 °C for 2–6 h under basic conditions. The reaction mixture was stirred to obtain 3-sulfamoyl coumarines 46 in 30–84% yield ( Scheme 6 ) [ 72 ].…”

Section: Coumarin Sulfonamides As Anti-cancer Agents and Carbonic Anh...mentioning

confidence: 99%

Section: Coumarin Sulfonamides As Anti-cancer Agents and Carbonic Anh...mentioning

confidence: 99%

“…Kurt and coworkers in 2019 developed coumarin sulfonamde motifs 53a-i by consec the evaluation of carbonic anhydrases (CA I, potential against human colorectal adenocarci embryonic kidney cells lines. In the first step 1,3-dibromopropane to furnish scaffold 48, wh to afford propylazide bearing coumarin deriv [72]. The 3-sulfonamide substituted coumarin derivatives screened for their in metalloenzyme human carbonic anhydrase inhibitor, such as hCA I, II, IX, and XII 3-sulfonamide-substituted naphthalene coumaryl derivative 46a (Figure 8) showed the incorporation of extra aromatic rings may be detrimental for the anti-hCA activ 3-sulfamoyl coumarins.…”

Section: Pyrazole-based Coumarin Sulfonamides As Ca Inhibitors and An...mentioning

confidence: 99%

“…The promising compound 46a was not the strongest CA IX/XII inhibitor, and apoptosis was induced by activating caspases in a dose-dependent manner. The DNA intercalation mechanism was followed by this compound 46a for anti-proliferative effects, and so this compound has the potential to become a viable lead motif for the further development of next-generation anticancer agents [72]. Kurt and coworkers in 2019 developed a synthetic approach to achieve the target coumarin sulfonamde motifs 53a-i by consecutive reactions from various substrates for the evaluation of carbonic anhydrases (CA I, II, IX, and XII) inhibition and cytoxicities potential against human colorectal adenocarcinoma cell line HT-29 and healthy HEK293T embryonic kidney cells lines.…”

Section: Pyrazole-based Coumarin Sulfonamides As Ca Inhibitors and An...mentioning

confidence: 99%

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An Update on Synthesis of Coumarin Sulfonamides as Enzyme Inhibitors and Anticancer Agents

et al. 2022

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Coumarin is an important six-membered aromatic heterocyclic pharmacophore, widely distributed in natural products and synthetic molecules. The versatile and unique features of coumarin nucleus, in combination with privileged sulfonamide moiety, have enhanced the broad spectrum of biological activities. The research and development of coumarin, sulfonamide-based pharmacology, and medicinal chemistry have become active topics, and attracted the attention of medicinal chemists, pharmacists, and synthetic chemists. Coumarin sulfonamide compounds and analogs as clinical drugs have been used to cure various diseases with high therapeutic potency, which have shown their enormous development value. The diversified and wide array of biological activities such as anticancer, antibacterial, anti-fungal, antioxidant and anti-viral, etc. were displayed by diversified coumarin sulfonamides. The present systematic and comprehensive review in the current developments of synthesis and the medicinal chemistry of coumarin sulfonamide-based scaffolds give a whole range of therapeutics, especially in the field of oncology and carbonic anhydrase inhibitors. In the present review, various synthetic approaches, strategies, and methodologies involving effect of catalysts, the change of substrates, and the employment of various synthetic reaction conditions to obtain high yields is cited.

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Section: Coumarin Sulfonamides As Anti-cancer Agents and Carbonic Anh...mentioning

confidence: 99%

Section: Coumarin Sulfonamides As Anti-cancer Agents and Carbonic Anh...mentioning

confidence: 99%

Section: Pyrazole-based Coumarin Sulfonamides As Ca Inhibitors and An...mentioning

confidence: 99%

Section: Pyrazole-based Coumarin Sulfonamides As Ca Inhibitors and An...mentioning

confidence: 99%

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An Update on Synthesis of Coumarin Sulfonamides as Enzyme Inhibitors and Anticancer Agents

et al. 2022

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“…Commercially available 1-boc piperazine (1) reacted at ice-bath temperature with chloroacetyl chloride in the presence of the base, to afford 2 in 70-90% yield. During the addition of Over the years, coumarin has become an important core structure in drug design and has been widely used to synthesize compounds with anti-inflammatory, anti-Alzheimer, antioxidant, antimicrobial, anticancer, and antiepileptic activities [11][12][13][14][15][16]. However, its antidepressant effects have not been widely documented.…”

Section: Chemistrymentioning

confidence: 99%

Design, Synthesis, and In Vivo and In Silico Evaluation of Coumarin Derivatives with Potential Antidepressant Effects

et al. 2021

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In this study, a series of coumarin derivatives were designed and synthesized, their structures were characterized using nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS) testing methods. In the pharmacological experiment, two behavior-monitoring methods, the forced swim test (FST) and the tail suspension test (TST), were used to determine the antidepressant activity of coumarin derivatives. Compounds that showed potential activity were analyzed for their effects on 5-hydroxytryptamine (5-HT) levels in the brains of mice. Molecular docking experiments to simulate the possible interaction of these compounds with the 5-HT1A receptor was also be predicted. The results of the pharmacological experiments showed that most coumarin derivatives exhibited significant antidepressant activity. Among these compounds, 7-(2-(4-(4-fluorobenzyl)piperazin-1-yl)-2-oxoethoxy)-2H-chromen-2-one (6i) showed the highest antidepressant activity. The results of the measurement of 5-HT levels in the brains of mice indicate that the antidepressant activity of coumarin derivatives may be mediated by elevated 5-HT levels. The results of molecular docking demonstrated that compound 6i had a significant interaction with amino acids around the active site of the 5-HT1A receptor in the homology model. The physicochemical and pharmacokinetic properties of the target compounds were also predicted using Discovery Studio (DS) 2020 and Chemdraw 14.0.

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Novel metabolic enzyme inhibitors designed through the molecular hybridization of thiazole and pyrazoline scaffolds

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et al. 2021

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New hybrid thiazolyl-pyrazoline derivatives (4a-k) were obtained through a facile and versatile synthetic procedure, and their inhibitory effects on the human carbonic anhydrase (hCA) isoforms I and II as well as on acetylcholinesterase (AChE) were determined.All new thiazolyl-pyrazolines showed activity at nanomolar levels as hCA I, hCA II, and AChE inhibitors, with K I values in the range of 13.35-63.79, 7.01-115.80, and 17.89-48.05 were identified as highly potent inhibitors, superior to the standard drugs, acetazolamide and tacrine, respectively. Compounds 4a-k were also evaluated for their cytotoxic effects on the L929 mouse fibroblast (normal) cell line. Moreover, a comprehensive ligand-receptor interaction prediction was performed using the ADME-Tox, Glide XP, and MM-GBSA modules of the Schrödinger Small-Molecule Drug Discovery Suite to elucidate the potential binding modes of the new hybrid inhibitors against these metabolic enzymes.

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Investigation of 3-sulfamoyl coumarins against cancer-related IX and XII isoforms of human carbonic anhydrase as well as cancer cells leads to the discovery of 2-oxo-2H-benzo[h]chromene-3-sulfonamide – A new caspase-activating proapoptotic agent

Cited by 18 publications

References 77 publications

An Update on Synthesis of Coumarin Sulfonamides as Enzyme Inhibitors and Anticancer Agents

An Update on Synthesis of Coumarin Sulfonamides as Enzyme Inhibitors and Anticancer Agents

Design, Synthesis, and In Vivo and In Silico Evaluation of Coumarin Derivatives with Potential Antidepressant Effects

Novel metabolic enzyme inhibitors designed through the molecular hybridization of thiazole and pyrazoline scaffolds

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