Pyrrolopyrazine derivatives: synthetic approaches and biological activities

Dehnavi, Fateme; Alizadeh, Seyedeh Roya; Ebrahimzadeh, Mohammad Ali

doi:10.1007/s00044-021-02792-9

Cited by 6 publications

(11 citation statements)

References 209 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Moreover, as 1,2,4-triazole-fused heterocycles are a key motif of many bioactive molecules as well as medicines currently used (Fig. 1), 7 we anticipated that our polyfunctionalized 1,2,4-triazole-pyrrolo[1,2- a ]pyrazine 8 hybrid skeleton may exhibit intriguing biological activities. Here we wish to report our results on these findings.…”

Section: Introductionmentioning

confidence: 99%

Catalyst-free assembly of a polyfunctionalized 1,2,4-triazole-fused N-heterocycle, 6-acylated pyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine

Oh,

Kim

2024

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 99%

Catalyst-free assembly of a polyfunctionalized 1,2,4-triazole-fused N-heterocycle, 6-acylated pyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine

Oh,

Kim

2024

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

“…They are known for their strong pharmacological activity. Pyrrolo[1,2-a]pyrazines and structural analogues show a wide range of biological effects [1,2], as illustrated by reports on their anxiolytic [3], anticancer [4,5], and antifungal activity [1,6], as well as their use as insect feeding deterrents [7] and potent and selective non-competitive antagonists of mGluR5 [8]. Antibiotic activity has only been found for the hexahydropyrrolo[1,2-a]pyrazine-1,4-dione analogues, which provides a strong effect against gram-negative bacteria [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

“…However, the antifungal effect of indolizines is modest [12]. Although the mechanism of action is not clearly established for either heterocycle, it is probably associated with the nitrogen-bridged heterocyclic scaffold [1,12].…”

Section: Introductionmentioning

confidence: 99%

“…Although pyrrolo [1,2-a]pyrazines have received less attention from researchers than indolizines, their broad spectrum of activity has stimulated the discovery of versatile synthetic strategies [1,2]. One of the most efficient approaches involves pyrrole-containing substrates, which undergo a cyclization process to build the pyrazine ring [20][21][22][23][24] (Scheme 1a).…”

Section: Introductionmentioning

confidence: 99%

“…The aim of the current contribution was to design and test new synthetic approaches for synthesizing pyrrolo [1,2-a]pyrazines and indolizines. For the elaboration of pyrrolo [1,2a]pyrazines, the potential of the annulation of 2-formylpyrrole-based enaminones (1)(2)(3) in the presence of ammonium acetate was evaluated. On the other hand, analogous enaminones were exposed to Lewis acids to prepare indolizines (Scheme 1d).…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Pyrrole-Based Enaminones as Building Blocks for the Synthesis of Indolizines and Pyrrolo[1,2-a]pyrazines Showing Potent Antifungal Activity

Miranda-Sánchez,

Escalante,

Andrade-Pavón

et al. 2023

Molecules

View full text Add to dashboard Cite

As a new approach, pyrrolo[1,2-a]pyrazines were synthesized through the cyclization of 2-formylpyrrole-based enaminones in the presence of ammonium acetate. The enaminones were prepared with a straightforward method, reacting the corresponding alkyl 2-(2-formyl-1H-pyrrol-1-yl)acetates, 2-(2-formyl-1H-pyrrol-1-yl)acetonitrile, and 2-(2-formyl-1H-pyrrol-1-yl)acetophenones with DMFDMA. Analogous enaminones elaborated from alkyl (E)-3-(1H-pyrrol-2-yl)acrylates were treated with a Lewis acid to afford indolizines. The antifungal activity of the series of substituted pyrroles, pyrrole-based enaminones, pyrrolo[1,2-a]pyrazines, and indolizines was evaluated on six Candida spp., including two multidrug-resistant ones. Compared to the reference drugs, most test compounds produced a more robust antifungal effect. Docking analysis suggests that the inhibition of yeast growth was probably mediated by the interaction of the compounds with the catalytic site of HMGR of the Candida species.

show abstract

Exploring the natural efficacy of spirulina powder for combating obesity, diabetes, and inflammation

Krishnan,

Kaushik,

Kumar

et al. 2024

J Sci Food Agric

View full text Add to dashboard Cite

BACKGROUNDAn increasing incidence of metabolic disorders emphasizes the need to explore natural treatments. Spirulina, a microalga with a rich nutrient profile, offers a promising solution for obesity, diabetes, and inflammation. This study provides a meticulous analysis of spirulina powder, evaluating its physicochemical attributes and technofunctional properties through the use of advanced analytical techniques.RESULTSSpirulina powder demonstrated strong flowability, substantial water and oil absorption capacity, and moderate foaming characteristics. The ethanolic extract of spirulina was found to be a repository of phenolic (6.93 mg GAE/g) and flavonoid (7.17 mg QE/g) compounds, manifesting considerable antioxidant activity with a 58.49 g kg−1 inhibition of 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) radicals. The extract also exhibited pronounced inhibitory effects on lipase and amylase enzymes, with inhibition percentages of 72.05 g kg−1 and 70.28 g kg−1, respectively, and displayed a glucose retention capacity of 1.28 mg dL−1 (68.52 g kg−1) in a dialysis membrane assay. These results suggest its efficacy in modulating obesity and glycemic control. The powder also showed a potent anti‐inflammatory response by mitigating protein denaturation.CONCLUSIONSpirulina powder is a potent natural agent with multiple health benefits, meriting its incorporation into functional foods. It could be suitable for application in the food industry, offering a natural strategy to combat metabolic diseases. This research adds to the scientific literature on spirulina, paving the way for future research into its utilization. © 2024 The Author(s). Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

show abstract

Pyrrolopyrazine derivatives: synthetic approaches and biological activities

Cited by 6 publications

References 209 publications

Catalyst-free assembly of a polyfunctionalized 1,2,4-triazole-fused N-heterocycle, 6-acylated pyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine

Catalyst-free assembly of a polyfunctionalized 1,2,4-triazole-fused N-heterocycle, 6-acylated pyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine

Pyrrole-Based Enaminones as Building Blocks for the Synthesis of Indolizines and Pyrrolo[1,2-a]pyrazines Showing Potent Antifungal Activity

Exploring the natural efficacy of spirulina powder for combating obesity, diabetes, and inflammation

Contact Info

Product

Resources

About