Synthesis, characterization and biological evaluation of tertiary sulfonamide derivatives of pyridyl-indole based heteroaryl chalcone as potential carbonic anhydrase IX inhibitors and anticancer agents

Peerzada, Mudasir Nabi; Khan, Parvez; Ahmad, Kamal; Hassan, Md. Imtaiyaz

doi:10.1016/j.ejmech.2018.05.034

Cited by 81 publications

(36 citation statements)

References 37 publications

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“…Disappointingly, a large fraction of publications on the subject reported compounds' cytotoxicity data obtained in normoxic conditions thus making the involvement of hCA IX and XII debateable [30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45] . Although such testing can be relevant in some cases, we consider these conditions irrelevant as long as antiproliferative activity of hCA inhibitors is concerned.…”

Section: Discussionmentioning

confidence: 99%

“…Understanding the significance of the candidate molecule prioritisation problem in question is essential while ignoring it may lead to many promising compounds being overlooked in want of more potent hCA IX/XII inhibitors. Aiming to draw a more informative picture, we have graphically represented the relationship between the anticancer effect (in this case, irrespective of the specific experimental conditions employed in various studies) and the hCA IX/XII inhibitory activity of the compounds [30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45][49][50][51][52][53][54][55][56][57][58][71][72][73][74] . In order to summarise the somewhat heterogeneous literature data, we have visualised the reported antiproliferative agents in the plots with the Y-axis displaying K i 's against hCA IX (Figures S1 and S2) and hCA XII ( Figures S3 and S4).…”

Section: Discussionmentioning

confidence: 99%

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Inhibitory activity against carbonic anhydrase IX and XII as a candidate selection criterion in the development of new anticancer agents

Krasavin

Kalinin

Sharonova

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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Analysis of the literature data reveals that while inhibition of cancer-related carbonic anhydrase IX and XII isoforms continues to be an important enrichment factor for designing anticancer agent development libraries, exclusive reliance on the in vitro inhibition of these two recombinant isozymes in nominating candidate compounds for evaluation of their effects on cancer cells may lead not only to identifying numerous compounds devoid of the desired cellular efficacy but also to overlooking many promising candidates which may not display the best potency in biochemical inhibition assay. However, SLC-0111, now in phase Ib/II clinical trials, was developed based on the excellent agreement between the in vitro, in vivo and more recently, in-patient data.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Inhibitory activity against carbonic anhydrase IX and XII as a candidate selection criterion in the development of new anticancer agents

Krasavin

Kalinin

Sharonova

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In every other latest report, tertiary sulfonamide derivatives of pyridyl-indole based totally heteroaryl chalcone were synthesized and tested as CA IX inhibitors (Fig. 37) [58]. The results of this observe served as an illustration that tertiary arylsulfonamides may also function lead compounds within the improvement of non-zincbinding inhibitors with anticancer properties that can also selectively bind to CA IX isoforms [58].…”

Section: I-alzheimer's Diseasementioning

confidence: 98%

Sulfonamides: Synthesis and the recent applications in Medicinal Chemistry

et al. 2020

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This review spotlights on sulfonamides from different sides, including history, structure-activity relationship, chemistry, methods of classification and up to date ways for their synthesis. Moreover, the review includes a discussion of the varied pharmacological effects of sulfonamides. Sulfonamides have a good range of pharmacological activities like oral diuretics (furosemide, indapamide, chlorthalidone, thiazides); anticancer (E7070), carbonic anhydrase (CA) inhibitors (CAIs) (acetazolamide, dichlorophenamide, dorzolamide and brinzolamide), antiepileptics (zonisamide and sulthiame), for rheumatoid arthritis (Sulfasalazine) antiviral (Darunavir) anti-inflammatory (celecoxib), antibacterial (Sulfadizine), as ophthamologicals (Dorzolamide) anticonvulsant (Zonisamide) cycloxygenase 2 (COX2) inhibitors (valdecoxib). These days, novel pills are launched, like apricoxib and pazopanib, which additionally include this organization. The sulfonamides competitively inhibit vitamin Bc synthesis in microorganisms and subsequently inhibit multiplication of bacteria but donot actively kill them. They need been used against most gram-positive and lots of gram-negative bacteria, also as some fungi.

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“…Other Brønsted acids failed completely (Table S2, SI). As piperidine has been reported to promote aldol condensations, [44][45][46] aldehyde 10b was submitted to condensation in the presence of piperi-…”

Section: Feature Syn Thesismentioning

confidence: 99%

Asymmetric Organocatalysis Revisited: Taming Hydrindanes with Jørgensen–Hayashi Catalyst

Stöckl¹,

Frey²,

Lang³

et al. 2018

Synthesis

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The organocatalytic Michael reaction of easily available 1-cyclopentene-1-carbaldehyde and 1,3-dicarbonyl compounds led to cyclopentanecarbaldehydes on a gram scale with low catalyst loading (2 mol%) and high enantioselectivity. The synthetic potential of 4-acylhexahydroindenones from intramolecular aldol condensation was demonstrated by Diels–Alder reaction to a tetracyclic derivative with seven stereogenic centers. The diastereofacial preference of the tetracyclic product was confirmed by DFT calculations. The described reaction sequence is characterized by few redox-economic steps and high degree of molecular complexity.

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Synthesis, characterization and biological evaluation of tertiary sulfonamide derivatives of pyridyl-indole based heteroaryl chalcone as potential carbonic anhydrase IX inhibitors and anticancer agents

Cited by 81 publications

References 37 publications

Inhibitory activity against carbonic anhydrase IX and XII as a candidate selection criterion in the development of new anticancer agents

Inhibitory activity against carbonic anhydrase IX and XII as a candidate selection criterion in the development of new anticancer agents

Sulfonamides: Synthesis and the recent applications in Medicinal Chemistry

Asymmetric Organocatalysis Revisited: Taming Hydrindanes with Jørgensen–Hayashi Catalyst

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