2-Aminothiophene scaffolds: Diverse biological and pharmacological attributes in medicinal chemistry

Bozorov, Khurshed; Nie, Li; Zhao, Jiaheng; Aisa, Haji Akber

doi:10.1016/j.ejmech.2017.09.039

Cited by 92 publications

(52 citation statements)

References 99 publications

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“…Novel fused triazole 6-methyl-4,5,6,7-tetrahydro-1H- [1,2,3]triazolo [4,5-c]pyridine derivatives were synthesised as P2X7 receptor antagonists by Chrovian et al 138 The 1,2,3-triazole-fused lead 109 (Fig. 14) increased the plasma free fraction that exhibited potential P2X7 receptor occupancy in the hippocampus of rats, with a low ED 50 value of 0.07 mg/kg, and unbound plasma EC 50 value of 12 ng/mL.…”

Section: 23-triazoles As Neuroprotective Agentsmentioning

confidence: 99%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

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575

289

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A B S T R A C TThe 1,2,3-triazole ring is a major pharmacophore system among nitrogen-containing heterocycles. These fivemembered heterocyclic motifs with three nitrogen heteroatoms can be prepared easily using 'click' chemistry with copper-or ruthenium-catalysed azide-alkyne cycloaddition reactions. Recently, the 'linker' property of 1,2,3-triazoles was demonstrated, and a novel class of 1,2,3-triazole-containing hybrids and conjugates was synthesised and evaluated as lead compounds for diverse biological targets. These lead compounds have been demonstrated as anticancer, antimicrobial, anti-tubercular, antiviral, antidiabetic, antimalarial, anti-leishmanial, and neuroprotective agents. The present review summarises advances in lead compounds of 1,2,3-triazolecontaining hybrids, conjugates, and their related heterocycles in medicinal chemistry published in 2018. This review will be useful to scientists in research fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology. Chemistry: synthesis and properties of the 1,2,3-triazolesThe general synthetic route of 1,2,3-triazoles using click chemistry is described in Scheme 1A. The most popular route to 1,2,3-triazoles is Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition, which is the https://doi.

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Section: 23-triazoles As Neuroprotective Agentsmentioning

confidence: 99%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

Self Cite

575

289

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“…Keywords: sulfur; 2-aminothiophene; chalcone; arylacetonitrile; oxidative sulfuration Substituted 2-aminothiophenes occupy an important place in thiophene chemistry because of their fascinating biological activities [1] such as antiviral, [2] anticancer, [3] anti-tubercular, antimicrobial, [4,5] antioxidants, [6] kinase inhibitors, [7] as well as various beneficial effects on neurological disorders. [8] Olanzapine, sold under the trade name Zyprexa among others, is an atypical antipsychotic primarily used to treat schizophrenia and bipolar disorder.…”

Section: Introductionmentioning

confidence: 99%

Access to 2‐Amino‐3‐Arylthiophenes by Base‐Catalyzed Redox Condensation Reaction Between Arylacetonitriles, Chalcones, and Elemental Sulfur

Nguyen

Retailleau

et al. 2019

Adv Synth Catal

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A straightforward access to 2‐amino‐3‐arylthiophenes has been developed via one‐pot two‐step three‐component reaction of arylacetonitriles, chalcones and elemental sulfur. The first step consists of a DBU‐catalyzed formation of Michael adduct between arylacetonitriles and chalcones. The second step is a cascade of DABCO‐catalyzed sulfuration of the Michael adduct with elemental sulfur followed by an oxidative cyclization to afford thiophenes. Compared to the Gewald reactions and related transformations which are limited in acetonitriles bearing a methylene group activated by an α‐substituted electron withdrawing group as substrates, our method can be applied to a wide range of arylacetonitriles and requires only catalytic amounts of DBU and DABCO. The developed reaction opens an access to 3‐aryl‐2‐aminothiophenes complementary to classical Gewald reactions with high degree of structural diversity and atom efficiency.

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“…Thiophene and its derivatives are an important class of heterocyclic compounds possessing broad biological activities; [1,2] thiophenes and thienopyridines are present in many pharmacologically active compounds and natural products, [3] e. g., the antiplatelet aggregation clopidogrel, the anticonvulsant tiagabine, antimuscarinic drugs for the treatment of asthma and bronchospasm such as tiotropium bromide, antiinflammatory, [4] antimicrobial, [5] and antiviral derivatives. [6] For these reasons, the development of an efficient, rapid, and clean synthetic route towards focused libraries of such compounds is of great importance to both medicinal and synthetic chemists.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of Novel Chiral 2‐Amino‐4,5,6,7‐tetrahydrothieno[2,3‐c]pyridine Derivatives

Rossetti

Bono

Candiani

et al. 2019

Chemistry & Biodiversity

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New N‐substituted‐2‐amino‐4,5,6,7‐tetrahydrothieno[2,3‐c]pyridine derivatives were synthesized employing a convenient one‐pot three‐component method and their structures were characterized by 1H‐NMR and single crystal X‐ray diffraction analysis. All the synthesized compounds were in vitro screened for antimicrobial activity against Gram‐positive (Sarcina lutea) and Gram‐negative bacteria (Escherichia coli). In this work, we introduced a chiral residue on the tetrahydropyridine nitrogen, the hitherto the less investigated position on this pharmacophore in order to explore the effect. The antibacterial results showed that the synthesized compounds were active only against Gram‐positive bacteria and the (R)‐enantiomers displayed a greater antimicrobial potency than their (S)‐counterparts. The structure–activity relationship here investigated may provide some interesting clues for future development of tetrahydrothienopyridine derivatives with higher antimicrobial activity.

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2-Aminothiophene scaffolds: Diverse biological and pharmacological attributes in medicinal chemistry

Cited by 92 publications

References 99 publications

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Access to 2‐Amino‐3‐Arylthiophenes by Base‐Catalyzed Redox Condensation Reaction Between Arylacetonitriles, Chalcones, and Elemental Sulfur

Synthesis and Antimicrobial Evaluation of Novel Chiral 2‐Amino‐4,5,6,7‐tetrahydrothieno[2,3‐c]pyridine Derivatives

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