Synthesis, carbonic anhydrase inhibition and cytotoxic activity of novel chromone-based sulfonamide derivatives

Awadallah, Fadi M.; El-Waei, Tamer A.; Hanna, Mona M.; Abbas, Samir Y.; Ceruso, Mariangela; Oz, Beyza Ecem; Guler, Ozen Ozensoy; Supuran, Claudiu T.

doi:10.1016/j.ejmech.2015.04.033

Cited by 51 publications

(35 citation statements)

References 45 publications

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“…2533K i value of 19.91 and 32.09 nM, respectively. Although, against hCA XII, 314 and 315 have shown a K i value of 22.8 and 10.7 nM, respectively316 Carradori et al synthesized Salen and tetrahydrosalen derivatives with micromolar Chemical structure of compounds 304-317 with selective hCA IX/hCA XII inhibitory action. hCA, human carbonic anhydrase studies.…”

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confidence: 99%

Progress in the development of human carbonic anhydrase inhibitors and their pharmacological applications: Where are we today?

Mishra

Tiwari

Supuran

2020

Medicinal Research Reviews

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188

166

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Carbonic anhydrases (CAs, EC 4.2.1.1) are widely distributed metalloenzymes in both prokaryotes and eukaryotes. They efficiently catalyze the reversible hydration of carbon dioxide to bicarbonate and H + ions and play a crucial role in regulating many physiological processes. CAs are wellstudied drug target for various disorders such as glaucoma, epilepsy, sleep apnea, and high altitude sickness. In the past decades, a large category of diverse families of CA inhibitors (CAIs) have been developed and many of them showed effective inhibition toward specific isoforms, and effectiveness in pathological conditions in preclinical and clinical settings. The discovery of isoform-selective CAIs in the last decade led to diminished side effects associated with off-target isoforms inhibition. The many new classes of such compounds will be discussed in the review, together with strategies for their development. Pharmacological advances of the newly emerged CAIs in diseases not usually associated with CA inhibition (neuropathic pain, arthritis, cerebral ischemia, and cancer) will also be discussed.

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mentioning

confidence: 99%

Progress in the development of human carbonic anhydrase inhibitors and their pharmacological applications: Where are we today?

Mishra

Tiwari

Supuran

2020

Medicinal Research Reviews

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188

166

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“…In 2015, Awadallah et al 21 reported a similar reaction performed in methanol, ethanol and n-butanol, resulting in corresponding 2-alkoxy derivatives 12. Acetic acid was used as catalyst (Scheme 6).…”

Section: Dicarbonyl Derivatives Of Methylaminobenzene-sulfonamidementioning

confidence: 99%

“…Moreover, the most potent compounds from this series were tested in vitro against MCF-7 breast cancer and A-549 lung cancer cell lines and Figure 3. Biological activity data for the lead compound 12 reported by Awadallah et al 21 . demonstrated fairly potent cytotoxic activity with IC 50 's in micromolar range (Figure 3).…”

Section: Dicarbonyl Derivatives Of Methylaminobenzene-sulfonamidementioning

confidence: 99%

Multicomponent chemistry in the synthesis of carbonic anhydrase inhibitors

Kalinin

Supuran

Krasavin

2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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Carbonic anhydrase inhibitors (CAIs) are of growing interest since various isoforms of the enzyme are identified as promising drug targets for treatment of disease. The principal drawback of the clinically used CAIs is the lack of isoform selectivity, which may lead to observable side effects. Studies aiming at the design of isoform-selective CAIs entail generation and biological testing of arrays of compounds, which is a resource-and time-consuming process. Employment of multicomponent reactions is an efficient synthetic strategy in terms of gaining convenient and speedy access to a range of scaffolds with a high degree of molecular diversity. However, this powerful tool appears to be underutilized for the discovery of novel CAIs. A number of studies employing multicomponent reactions in CAI synthesis have been reported in literature. Some of these reports provide inspiring examples of successful use of multicomponent chemistry to construct novel potent and often isoform-selective inhibitors. On critical reading of several publications, however, it becomes apparent that for some chemical series designed as CAIs, the desired inhibitory properties are only assumed and never tested for. In these cases, the biological profile is reported based on the results of phenotypical cellular assays, with no correlation with the intended on-target activity. Present review aims at critically assessing the current literature on the multicomponent chemistry in the CAI design.

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“…Cyclocondensation of phenacyl bromide derivative 2 with o-aminothiophenol afforded benzo[b] [1,4]thiazine derivative 31. Similarly treatment of 2 with 1H-benzo [d]imidazole-2-thiol afforded benzo [4,5]imidazo[2,1-b]thiazole derivative 33 via cyclization of acyclic intermediate 32 by dehydration under the reaction conditions (Scheme7).…”

Section: Chemistrymentioning

confidence: 99%

“…Sulfonamides have been demonstrated to possess antibacterial [1]- [3], antifungal [4], insulin-releasing [5] [6], carbonic anhydrase inhibitory [7]- [9], hypoglycemic [10], anesthetic [11], anti-inflammatory [12] [13], andanticarcinogenic [14] [15] activities. Liver cancer (hepatocellular carcinoma) remains one of the most important health problems in the world because it is the third foremost cause of cancer-related deaths worldwide [16].…”

Section: Introductionmentioning

confidence: 99%

1-(4-(Pyrrolidin-1-ylsulfonyl)phenyl) ethanone in Heterocyclic Synthesis: Synthesis, Molecular Docking and Anti-Human Liver Cancer Evaluation of Novel Sulfonamides Incorporating Thiazole, Imidazo[1,2-a]pyridine, Imidazo[2,1-c] [1,2,4]triazole, Imidazo[2,1-b]thiazole, 1,3,4-Thiadiazine and 1,4-Thiazine Moieties

Bashandy¹

2015

IJOC

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This article describes the synthesis of some novel sulfonamides having the biologically active, thiazole 4-6, 8, 10-12a,b, 20, 22, 34, 35, imidazo[1,2-a]pyridine 14, imidazo[2,1-c][1,2,4]triazole 15, imidazo[2,1-b]thiazole 23, 24, 33, nicotinonitrile 25, 1,3,4-thiadiazine 27, quinoxaline 30 and 1,4thiazine 31 moieties, starting with 1-(4-(pyrrolidin-1-ylsulfonyl)phenyl)ethanone (1). The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, 1 H NMR, 13 C NMR and Ms spectral data. All the compounds were tested in-vitro antihuman liver hepatocellular carcinoma cell line (HepG2). Compounds 8, 11, 4, 22, 12a, 33, 35, 27 and 24 with selectivity index (SI) values of 33.21, 30.49, 19.43, 14.82, 10.29, 7.3, 6.87, 6.15 and 4.62, respectively, exhibited better activity than methotrexate (MTX) as a reference drug with SI value of 4.14. Molecular Operating Environment (MOE) performed virtual screening using molecular docking studies of the synthesized compounds. The results indicated that some synthesized compounds are suitable inhibitors against dihydrofolate reductase (DHFR) enzyme (PDB ID: 4DFR) with further modification. M. S. Bashandy 167

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Synthesis, carbonic anhydrase inhibition and cytotoxic activity of novel chromone-based sulfonamide derivatives

Cited by 51 publications

References 45 publications

Progress in the development of human carbonic anhydrase inhibitors and their pharmacological applications: Where are we today?

Progress in the development of human carbonic anhydrase inhibitors and their pharmacological applications: Where are we today?

Multicomponent chemistry in the synthesis of carbonic anhydrase inhibitors

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