Nitrogen-Containing Heterocycles as Significant Molecular Scaffolds for Medicinal and Other Applications

Frank, Éva; Szőllősi, György

doi:10.3390/molecules26154617

Cited by 17 publications

(7 citation statements)

References 14 publications

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“…As is widely known, the nitrogen heterocyclic scaffold serves as a core framework in many drug intermediates and drug molecules, which exhibit significant physiological and pharmacological activities. 26 In the field of pesticides, nitrogen heterocyclic compounds have become an important direction of pesticide development due to their high efficiency, low toxicity, and good environmental compatibility. 27,28 7-Nitrobenzo[c] [1,2,5] oxadiazole is an organic compound containing a nitrogen heterocyclic structure.…”

Section: ■ Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Investigations of Novel Carbamoylguanidinyl Nitrobenzoxadiazoles against Chitinolytic Enzymes

Li,

Zhao,

Chen

et al. 2023

J. Agric. Food Chem.

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Chitinase has been identified as an important target for insecticides. In this study, a series of novel chitinase inhibitors was designed and synthesized with nitrobenzoxadiazoles. Compound 8d, which contains the N-methylcarbamoylguanidinyl, exhibited high enzyme inhibitory activity and achieved nanomolar inhibition against Of ChtI (IC 50 = 12.3 nM). Delightfully, it was also found to possess significant inhibitory activity against Of Hex1 (IC 50 = 1.76 μM). The computational simulation results indicated that compound 8d interacted with Of ChtI and Of Hex1 in similar modes through hydrogen bonds and hydrophobic and π−π interactions. Insecticidal activity studies revealed that compound 8d showed high mortality against the Lepidoptera Plutella xylostella (mortality rate = 81%) at 200 mg/L. Toxicity studies indicated that compound 8d exhibited negligible toxicity to the natural enemy Trichogramma ostriniae. These results indicate that compound 8d may be a promising candidate for the development of environmentally friendly chitinase inhibitors. Moreover, this study provides a new angle for the design of innovative inhibitors of chitinolytic enzymes.

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Section: ■ Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Investigations of Novel Carbamoylguanidinyl Nitrobenzoxadiazoles against Chitinolytic Enzymes

Li,

Zhao,

Chen

et al. 2023

J. Agric. Food Chem.

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“…Nitrogen‐containing heterocycles are widely dispersed in natural products and pharmaceutical products, owing to their unique pharmacological activities [16] . As a representative nitrogen‐containing heterocyclic compound, 1,5‐benzodiazepine skeletons are widely used in biological and pharmaceutical fields due to their biological and pharmacological activities or as intermediates [17–21] .…”

Section: Introductionmentioning

confidence: 99%

“…[8][9][10][11][12][13][14][15] Nitrogen-containing heterocycles are widely dispersed in natural products and pharmaceutical products, owing to their unique pharmacological activities. [16] As a representative nitrogen-containing heterocyclic compound, 1,5-benzodiazepine skeletons are widely used in biological and pharmaceutical fields due to their biological and pharmacological activities or as intermediates. [17][18][19][20][21] Therefore, the development of efficient methods for the synthesis of the 1,5-benzodiazepine scaffold from simple substrates is highly desirable.…”

Section: Introductionmentioning

confidence: 99%

“…[a] reaction with different load of catalysts did not offer better results than the 30 mol% amount which was thus used in the next experiments (catalyst loading comparisons are provided in SI). With respect to the solvent, ethanol gave clearly the best results as compared to a collection of organic solvents such as MeCN, DCM, THF, 1,4-dioxane, DMSO or water (Table1, entries[14][15][16][17][18][19]. Finally, performing the reaction at 50 °C or 80…”

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Ammonium Acetate Catalyzed Formation of 1,5‐Benzodiazepines through [4+2+1] Cycloaddition Involving 5‐Hydroxymethylfurfural

2023

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The use of the renewable platform molecule 5‐hydroxymethylfurfural (5‐HMF) in multi‐component reaction with a diamine and an alkynone to generate seven‐membered 1,5‐benzodiazepines is described. Due to the sensitivity of 5‐HMF to strong acidic and basic conditions, the investigation required an in‐depth revisit of reaction parameters as compared to benchmark aldehydes. Among catalysts/solvents couples, ammonium acetate in ethanol proved to be a clean and efficient system. These optimized conditions were subsequently used to investigate the scope of the reaction providing a library of 1,5‐benzodiazepines in moderate to good yields from a wide range of diversely substituted diamines and alkynones or alkyl alkynoates.

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“…The pharmaceutical importance of N-heterocyclic compounds is indisputable [1]. Due to the biological activities of quinazolinone derivatives, such as anticancer, diuretic and antibacterial properties, these molecules caught the attention of organic chemists [2][3][4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a Pyrrolo[1,2-a]quinazoline-1,5-dione Derivative by Mechanochemical Double Cyclocondensation Cascade

Kolcsár

Szőllősi

2022

Molecules

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N-heterocyclic compounds, such as quinazolinone derivatives, have significant biological activities. Nowadays, as the demand for environmentally benign, sustainable processes increases, the application of compounds from renewable sources, easily separable heterogeneous catalysts and efficient, alternative activation methods is of great importance. In this study, we have developed a convenient, green procedure for the preparation of 3a-methyl-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazoline-1,5-dione through a double cyclocondensation cascade using anthranilamide and ethyl levulinate. Screening of various heterogeneous Brønsted acid catalysts showed that Amberlyst® 15 is a convenient choice. By applying mechanochemical activation in the preparation of this N-heterotricyclic compound for the first time, it was possible to shorten the necessary time to three hours compared to the 24 h needed under conventional conditions to obtain a high yield of the target product.

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Nitrogen-Containing Heterocycles as Significant Molecular Scaffolds for Medicinal and Other Applications

Abstract: Most of the organic compounds applied as pharmaceuticals or intermediates utilized in their synthesis contain heterocyclic motifs [...]

Cited by 17 publications

References 14 publications

Design, Synthesis, and Biological Investigations of Novel Carbamoylguanidinyl Nitrobenzoxadiazoles against Chitinolytic Enzymes

Design, Synthesis, and Biological Investigations of Novel Carbamoylguanidinyl Nitrobenzoxadiazoles against Chitinolytic Enzymes

Ammonium Acetate Catalyzed Formation of 1,5‐Benzodiazepines through [4+2+1] Cycloaddition Involving 5‐Hydroxymethylfurfural

Synthesis of a Pyrrolo[1,2-a]quinazoline-1,5-dione Derivative by Mechanochemical Double Cyclocondensation Cascade

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