Five-Membered Heterocyclic Sulfonamides as Carbonic Anhydrase Inhibitors

Angeli, Andrea; Paoletti, Niccolò; Supuran, Claudiu T.

doi:10.3390/molecules28073220

Cited by 13 publications

(2 citation statements)

References 97 publications

(130 reference statements)

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“…The various biological activities of 1,3,4-thiadiazole are antimicrobial, , antituberculosis, anti-inflammatory, , carbonic anhydrase inhibitory, anticonvulsant, , antihypertensive, , antioxidant, , anticancer, , and antifungal properties. Drug molecules that contain 1,3,4-thiadiazole groups in their structures and their examples are given, e.g., carbonic anhydrase inhibitors acetazolamide and methazolamide . The thiadiazole group was known to replace the thiazole moiety in a bioisosteric way .…”

Section: Introductionmentioning

confidence: 99%

“…Drug molecules that contain 1,3,4-thiadiazole groups in their structures and their examples are given, e.g., carbonic anhydrase inhibitors acetazolamide and methazolamide. 23 The thiadiazole group was known to replace the thiazole moiety in a bioisosteric way. 24 Due to this, the strong aromaticity of thiadiazole derivatives provides them with biological activity.…”

Section: Introductionmentioning

confidence: 99%

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New 1,3,4-Thiadiazole Derivatives as α-Glucosidase Inhibitors: Design, Synthesis, DFT, ADME, and In Vitro Enzymatic Studies

Ali,

Rehman,

Rasheed

et al. 2024

ACS Omega

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Diabetes is an emerging disorder in the world and is caused due to the imbalance of insulin production as well as serious effects on the body. In search of a better treatment for diabetes, we designed a novel class of 1,3,4-thiadiazole-bearing Schiff base analogues and assessed them for the α-glucosidase enzyme. In the series (1−12), compounds are synthesized and 3 analogues showed excellent inhibitory activity against αglucosidase enzymes in the range of IC 50 values of 18.10 ± 0.20 to 1.10 ± 0.10 μM. In this series, analogues 4, 8, and 9 show remarkable inhibition profile IC 50 2.20 ± 0.10, 1.10 ± 0.10, and 1.30 ± 0.10 μM by using acarbose as a standard, whose IC 50 is 11.50 ± 0.30 μM. The structure of the synthesized compounds was confirmed through various spectroscopic techniques, such as NMR and HREI-MS. Additionally, molecular docking, pharmacokinetics, cytotoxic evaluation, and density functional theory study were performed to investigate their behavior.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New 1,3,4-Thiadiazole Derivatives as α-Glucosidase Inhibitors: Design, Synthesis, DFT, ADME, and In Vitro Enzymatic Studies

Ali,

Rehman,

Rasheed

et al. 2024

ACS Omega

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In‐vitro and in‐silico investigations of SLC‐0111 hydrazinyl analogs as human carbonic anhydrase I, II, IX, and XII inhibitors

Sharma,

Vats,

Giovannuzzi

et al. 2024

Archiv der Pharmazie

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Two novel series of hydrazinyl‐based benzenesulfonamides 9a–j and 10a–j were designed and synthesized using SLC‐0111 as the lead molecule. The newly synthesized compounds were evaluated for their inhibitory activity against four different human carbonic anhydrase (hCA) isoforms I, II, IX, and XII. Both the series reported here were practically inactive against the off‐target isozyme hCA I. Notably, derivative 10a exhibited superior potency (Ki of 10.2 nM) than acetazolamide (AAZ) against the cytosolic isoform hCA II. The hCA IX and XII isoforms implicated in tumor progression were effectively inhibited with Kis in the low nanomolar range of 20.5–176.6 nM and 6.0–127.5 nM, respectively. Compound 9g emerged as the most potent and selective hCA IX and XII inhibitor with Ki of 20.5 nM and SI of 200.1, and Ki of 6.0 nM and SI of 683.7, respectively, over hCA I. Furthermore, six compounds (9a, 9h, 10a, 10g, 10i, and 10j) exhibited significant inhibition toward hCA IX (Kis = 27.0, 41.1, 27.4, 25.9, 40.7, and 30.8 nM) relative to AAZ and SLC‐0111 (Kis = 25.0 and 45.0 nM, respectively). These findings underscore the potential of these derivatives as potent and selective inhibitors of hCA IX and XII over the off‐target hCA I and II.

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Sulfonamide derivatives with benzothiazole scaffold: Synthesis and carbonic anhydrase I–II inhibition properties

Öztürk,

Kalay,

Gerni

et al. 2023

Biotech and App Biochem

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The secondary sulfonamide derivatives containing benzothiazole scaffold (1–10) were synthesized to determine their inhibition properties on two physiologically essential human carbonic anhydrases isoforms (hCAs, EC, 4.2.1.1), hCA I, and hCA II. The inhibitory effects of the compounds on hCA I and hCA II isoenzymes were investigated by comparing their IC50 and Ki values. The Ki values of compounds (1–10) against hCA I and hCA II are in the range of 0.052 ± 0.022–0.971 ± 0.280 and 0.025 ± 0.010–0.682 ± 0.335, respectively. Some of these inhibited the enzyme more effectively than the standard drug, acetazolamide. In particular, compounds 5 and 4 were found to be most effective on hCA I and hCA II.

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Five-Membered Heterocyclic Sulfonamides as Carbonic Anhydrase Inhibitors

Cited by 13 publications

References 97 publications

New 1,3,4-Thiadiazole Derivatives as α-Glucosidase Inhibitors: Design, Synthesis, DFT, ADME, and In Vitro Enzymatic Studies

New 1,3,4-Thiadiazole Derivatives as α-Glucosidase Inhibitors: Design, Synthesis, DFT, ADME, and In Vitro Enzymatic Studies

In‐vitro and in‐silico investigations of SLC‐0111 hydrazinyl analogs as human carbonic anhydrase I, II, IX, and XII inhibitors

Sulfonamide derivatives with benzothiazole scaffold: Synthesis and carbonic anhydrase I–II inhibition properties

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