Heterocycles 48. Synthesis, Characterization and Biological Evaluation of Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives as Anti-Inflammatory Agents

Cristina, Anamaria; Leonte, Denisa; Vlase, Laurian; Bencze, László Csaba; Imre, Silvia; Marc, Gabriel; Apan, Bogdan; Mogoşan, Cristina; Zaharia, Valentin

doi:10.3390/molecules23102425

Cited by 32 publications

(32 citation statements)

References 46 publications

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“…This reaction was carried out with acetone at room temperature in the presence of a base (NaOAc, Na 2 CO 3 ). The obtained thioesters can be converted to the corresponding thiazolo [3,2-b] [1,2,4]triazoles 1 under the action of sulfuric acid, [26][27][28][29][30] acetic anhydride in acidic medium, [21,[31][32][33] PPA, [34] pTSA, [35] or POCl 3. [36] Synthesis of thiazolo [3,2-b] [1,2,4]triazoles 1 proceeds through oxidative alkylation by acid condensation and MW radiation (Scheme 1).…”

Section: Synthesis Of Thiazolo [32-b][124]triazole Derivativesmentioning

confidence: 99%

Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

Slivka

Korol

Fizer

2020

Journal of Heterocyclic Chem

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Fused heterocyclic systems with 1,2,4‐triazole scaffold arouse great interest from researchers in the branch of heterocyclic and medical chemistry because of their wide biological activities as they are considered as fungicidal, antimicrobial, analgesic, bronchodilators, antioxidant, anti‐inflammatory agents, and they are G‐quadruple stabilizers; the molecular docking data for coumarin‐containing 1,2,4‐triazoles indicate their ability to act as a urease inhibitor. Therefore, the present review aims to investigate new trends in the chemistry of heterocycles incorporating thiazolo[3,2‐b][1,2,4]triazoles, thiazolo[2,3‐c][1,2,4]triazoles, thiazino[5,1‐b][1,2,4]triazoles, thiazino[3,4‐b][1,2,4]triazoles, triazolothiazepines, and their biological characteristics. The main sections discuss: (a) the synthetic routes to the production of substituted fused heterocyclic systems, which include condensation reactions, multiple bond annulation, and the reactions of electrophilic heterocyclization. (b) Description of chemical and biological characteristics of these fused heterocycles.

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Section: Synthesis Of Thiazolo [32-b][124]triazole Derivativesmentioning

confidence: 99%

Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

Slivka

Korol

Fizer

2020

Journal of Heterocyclic Chem

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“…In recent years, the imidazothiadiazole derivatives have been studied in depth for their wide‐ranging biological activities, as they possess antimicrobial, anticonvulsant, diuretic, anticancer, antitubercular, analgesic, and anti‐inflammatory properties. [ 14–16 ] Imidazothiadiazole derivative i (Figure 1) has been reported by Karki et al [ 17 ] to possess anticancer activity and derivative ii (Figure 1) has been reported by Kumar et al [ 18 ] as a potent tumor‐associated CA IX and XII inhibitor. Motivated by these findings, we envisioned to synthesize a novel series of imidazothiadiazole ( 5a – t ) scaffolds bearing 3‐functionalized benzenesulfonamide moiety and evaluated them for CA inhibition potential against hCA I, II, VA, and XII.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of benzenesulfonamide‐linked imidazo[2,1‐b][1,3,4]thiadiazole derivatives as carbonic anhydrase I and II inhibitors

Swain

Aashritha

Singh

et al. 2021

Archiv der Pharmazie

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A novel series of imidazothiadiazole‐linked benzenesulfonamide derivatives (5a–t) was synthesized and subjected for screening against the four physiologically and pharmacologically relevant human carbonic anhydrase (hCA) isoforms: hCA I, II, VA, and IX. The compounds selectively inhibited hCA I and II over hCA VA and IX. Furthermore, among the two cytosolic isoforms, hCA II was more effectively inhibited as compared with hCA I. The most active compounds were 5o with K i = 0.246 µM and 5p with K i = 0.376 µM against hCA II, whereas compound 5f showed good inhibition against both hCA I and II with K i = 0.493 and 0.4 µM, respectively. This class of underexplored sulfonamides may be used to design isoform‐selective CA inhibitors targeting enzymes of medicinal chemistry interest.

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“…[ 1,2 ] These compounds are having pharmaceutical [ 3 ] and biological significances [ 4 ] and huge synthetic advantages. Their therapeutic usages include anticancer, [ 5 ] antifungal, [ 6 ] antibacterial, [ 7 ] anti‐inflammatory, [ 8 ] and antioxidant. [ 9 ] They have applications in the field of veterinary products, agrochemicals, corrosion inhibitors, developers, copolymers and so on.…”

Section: Introductionmentioning

confidence: 99%

An overview of palladium‐catalyzed synthesis of seven‐membered heterocycles

Saranya

Neetha

Radhika

et al. 2020

Journal of Heterocyclic Chem

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Heterocyclic compounds are the ones that have always remained in the limelight owing to their superior contributions toward various disciplines such as biology, medicine, material science, pharmaceutical science, industry and so on. They form the building blocks of DNA and RNA macromolecules. Suitable tuning of these heterocyclic compounds can result in chemotherapeutic moieties with superlative efficiency. Seven‐membered heterocyclic compounds are an important class of heterocyclic chemistry. Some of them are azepine, oxepine, thiepine, diazepine, thiazepine and so on. Transition metal‐catalyzed synthesis of heterocycles has been the most explored in the recent past. Palladium is known as the best suitable catalyst for the same and that is the result of its excellent functional group tolerance and catalytic potency. Here, we intend to summarize the various investigations made on the palladium‐catalyzed synthesis of seven‐membered heterocycles. To the best of our knowledge, this is the first review in this topic and covers literature up to 2020.

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Heterocycles 48. Synthesis, Characterization and Biological Evaluation of Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives as Anti-Inflammatory Agents

Cited by 32 publications

References 46 publications

Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

Fused bicyclic 1,2,4‐triazoles with one extra sulfur atom: Synthesis, properties, and biological activity

Design and synthesis of benzenesulfonamide‐linked imidazo[2,1‐b][1,3,4]thiadiazole derivatives as carbonic anhydrase I and II inhibitors

An overview of palladium‐catalyzed synthesis of seven‐membered heterocycles

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