A class of carbonic anhydrase IX/XII – selective carboxylate inhibitors

Alhameed, Rakia Abd; Berrino, Emanuela; Almarhoon, Zainab M.; El‐Faham, Ayman

doi:10.1080/14756366.2020.1715388

Cited by 10 publications

(8 citation statements)

References 55 publications

(97 reference statements)

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“…The inhibition of the AChE enzyme results in the blockage of ACh hydrolysis. All compounds were again synthesised by one-pot three component cyclocondensation reaction from the amine, a substituted benzaldehyde and a mercaptocarboxylic acid [42][43][44][45].…”

Section: Discussionmentioning

confidence: 99%

An Insight into 4-Thiazolidinones

Sahu

Upadhyay

Mishra

2021

JPRI

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Aims: This assessment is all about to get imminent into 4-thiazolidinones and comprehensively reviewing this molecule. 4-Thiazolidinones are known for their wide-ranging biological activities. 4 - Thiazolidinones contains thiazolidine ring having carbonyl group in the 4-position. The chemistry of thiazolidinones has drawn scientiﬁc interest through the years because this particular ring system is the core structure in a variety of synthetic compounds with a broad spectrum of biological activities such as anti-bacterial, anti-fungal, insecticidal, anti-epileptic, anti-mycobacterial, anti- inflammatory, anti-parasitic, hypnotic and anti-cancer. Structural modiﬁcations on the 4-thiazolidinone moiety, either by replacing the aryl group with the heteroaryl scaffold or by incorporating different groups and moieties (A&B) on –CH– group of nucleus paving a new pathway for the future research. It necessitates to widely reviewing the structure, chemistry and pharmacological aspects of 4-thiazolidinones.

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Section: Discussionmentioning

confidence: 99%

An Insight into 4-Thiazolidinones

Sahu

Upadhyay

Mishra

2021

JPRI

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“…[61] Then, refluxing the pseudothiohydantoin 10 with hydrochloric acid for 8 : 10 hr gives TZD (Scheme 13). [62,63] Many modifications were made to this method, including one-pot synthesis or using microwave radiation for the acceleration of the reaction time. [64,65] Optimization of reaction conditions has shown that it can be carried out in water or hydrochloric acid.…”

Section: From Thioureamentioning

confidence: 99%

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

et al. 2023

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Thiazolidinedione (TZD) is one of the privileged heterocyclic rings and has shown many biological applications in medicinal chemistry and drug discovery. This review covers the synthetic approaches of TZD and its derivatives, different synthetic techniques for affording the desired regioselectivity and stereoselectivity, and the techniques that would enhance reaction conditions such as microwave, one‐pot, or ultrasound synthesis. It focuses on synthetic challenges of glitazones and the transformation of other heterocycles to TZD. Moreover, the chemical and biological behavior of TZD through the substitution in the N3 position, modification of the C5 position, annealing in complex heterocyclic systems, and hybridization with other pharmacologically attractive moieties are discussed. All reactions mentioned are provided as possible with different reaction conditions, mechanisms, derivatives scope, yield and clarified by applications of such reactions in the construction of potential medicinal agents. The review also answers questions about rapid racemization of glitazones, their toxicity, considering TZD as pan‐assay interference compounds (PAINS) or not, and the influence of saturation of 5‐position of TZD in their biological activities. This review is a comprehensive guide to make informed decisions for construction of TZD derivatives with biological potentials.

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“…[23] Alhameed et al reported 2,4-dioxothiazolidine acid derivatives (VIII) as selective carbonic anhydrase IX and XII inhibitors. [24] In the current work, we designed and synthesized four new, differently substituted Rhodanine derivatives and evaluated for their inhibitory activity against carbonic anhydrase I, II, IX, and XII isoforms. Interestingly, few tested compounds exhibited good to moderate inhibition against the cytosolic isoform hCA II and tumor-associated hCA IX.…”

Section: Rationalementioning

confidence: 99%

Design, synthesis, and structure–activity studies of new rhodanine derivatives as carbonic anhydrase II, IX inhibitors

Chinchilli,

Akunuri,

Ghouse

et al. 2023

Archiv der Pharmazie

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Rhodanine and its derivatives are an important class of heterocycles with diverse biological properties, including anticancer, antibacterial, and anti‐mycobacterial activities. In the present work, four series of new Rhodanine derivatives were synthesized and evaluated for their inhibitory activity against carbonic anhydrase I, II, IX, and XII isoforms. Interestingly, the tested compounds exhibited good inhibitory activity against the cytosolic isoform human carbonic anhydrase (hCA) II and tumor‐associated hCA IX. While the Rhodanine‐benzylidene derivatives (3a–l) and Rhodanine‐hydrazine derivatives (6a–e) are found to be selective against hCA II, the Rhodanine‐N‐carboxylate derivatives (8a–d) are found to be highly selective toward hCA IX. The Rhodanine‐linked isoxazole and 1,2,4‐oxadiazole derivatives (8ba, 8da, and 8db) exhibited inhibitory activity against hCA II and hCA IX. Among the tested compounds, 3b, 3j, 6d, and 8db were found to inhibit hCA II with Ki values of 9.8, 46.4, 7.7, and 4.7 µM, respectively. Furthermore, their mechanism of action is supported by molecular docking studies. Notably, the synthesized Rhodanine derivatives belong to a nonsulfonamide class of carbonic anhydrase inhibitors.

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A class of carbonic anhydrase IX/XII – selective carboxylate inhibitors

Cited by 10 publications

References 55 publications

An Insight into 4-Thiazolidinones

An Insight into 4-Thiazolidinones

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

Design, synthesis, and structure–activity studies of new rhodanine derivatives as carbonic anhydrase II, IX inhibitors

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