A Review on The Chemistry of Nicotinonitriles and Their applications

Shamroukh, Ahmed H.; Kotb, Eman R.; Anwar, Manal M.; Sharaf, M.

doi:10.21608/ejchem.2021.64971.3392

Cited by 14 publications

(10 citation statements)

References 69 publications

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“…Ortho aminonitrile derivatives are well known as a highly reactive and convenient reagents for the synthesis of nitrogen heterocycles [45, 46]. Herein, we report the synthesis of the pyrimidinone derivative 15 by the reaction of the imidazotriazole derivative 9 with 2‐amino‐4,5,6,7‐tetrahydrobenzo[b]thiophene‐3‐carbonitrile [47].…”

Section: Resultsmentioning

confidence: 99%

“…In this approach, we utilized those reagents for the synthesis of the tricyclic derivatives 13 and 14 via their cyclocondensation reaction with derivative 9. 13 Ortho aminonitrile derivatives are well known as a highly reactive and convenient reagents for the synthesis of nitrogen heterocycles [45,46]. Herein, we report the synthesis of the pyrimidinone derivative 15 by the reaction of the imidazotriazole derivative 9 with 2-amino-4,-5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile [47].…”

Section: Chemistrymentioning

confidence: 99%

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Imidazo[1,2,4]triazolone and fused imidazo[1,2,4]triazolone derivatives: Synthesis, in vitro anticancer screening, CDK2 inhibitory activity, and molecular modeling studies

Rabeeb

Deeb

Sarg

et al. 2022

Journal of Heterocyclic Chem

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In continuation of our program for synthesizing novel imidazotriazole scaffolds, we report herein the synthesis of new fifteen substituted and fused imidazotriazole derivatives via different addition and cyclocondensation pathways. Thirteen compounds have been tested for their antiproliferative activity against 60 NCI cell lines. Compounds 3, 15 and 17 were the most active among the synthesized series. Imidazo[2,1-c][1,2,4]triazolone derivative 3 showed high activity against leukemia K-562 (51.00%), RPMI-8226 (68.36%) and breast cancer MCF-7 (56.76%) cell lines. While compound 15 exhibited high potency against colon cancer HCT-15 (59.33%), CNS cancer SNB-75 (57.06%) and renal cancer UO-31 (50.5%) cell lines. Bis[1,2,4]triazolopurin-7-one derivative 17 showed strong activity against CNS cancer SNB-75 cell line (54.32%). Compounds 3, 15 and 17 were evaluated through molecular modeling and docking techniques to give us a closer look on their binding mode with CDK2. The in vitro inhibitory activity against CDK2 was also performed for compounds 3 and 17. Compound 3 was subjected to further investigations by studying its effect on cell cycle progression and cell apoptosis in MCF-7 cell line. It caused apoptosis, necrosis and induced cell cycle arrest at G2/M phase in MCF-7 cell.

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Section: Resultsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Imidazo[1,2,4]triazolone and fused imidazo[1,2,4]triazolone derivatives: Synthesis, in vitro anticancer screening, CDK2 inhibitory activity, and molecular modeling studies

Rabeeb

Deeb

Sarg

et al. 2022

Journal of Heterocyclic Chem

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“…The 1 Н NMR spectra of compounds 13 and 15 exhibit singlets at 4.47-4.64 ppm (SCH 2 ), as well as signals of the 5-hydroxypyran-4-one fragment at 6.47-6.59 (Н 3 ), 8.01-8.09 (Н 6 ), and 9.11-9.15 ppm (OH). The 13 C NMR spectra of compounds 13 and 15 contain characteristic In the context of the known biological activity of kojic acid derivatives [7][8][9][10][11], nicotinonitriles, and quinoxalines (for recent reviews see [55][56][57][58] and [59][60][61][62][63][64][65][66][67], respectively), it seemed appropriate to perform a preliminary in silico study of possible targets, ADMET parameters, and the bioavailability criteria for new hybrid molecules. Analysis of the structures for compliance with the "Lipinski's rule of five" [molecule mass (MW) ≤ 500, сLogP ≤ 5.0, TPSA ≤ 140 Å 2 , number of hydrogen bond acceptors ≤ 10, donors ≤ 5] [68-70] was carried out using the OSIRIS Property Explorer software service [71].…”

Section: Doi: 101134/s107036322109005xmentioning

confidence: 99%

Synthesis and Some Properties of New 5-Hydroxy-2-[(hetarylthio)methyl]-4H-pyran-4-ones

et al. 2021

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“…Nicotinonitriles, nicotinamides and their partially saturated analogs represent a promising class of heterocyclic compounds with an interesting profile of biological activity (for reviews, see [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 ]). However, while nicotinonitriles have been fairly well studied, the related synthetic nicotinamides and 1,4-dihydronicotinamides have been less studied and require further investigation.…”

Section: Introductionmentioning

confidence: 99%

New 6′-Amino-5′-cyano-2-oxo-1,2-dihydro-1′H-spiro[indole-3,4′-pyridine]-3′-carboxamides: Synthesis, Reactions, Molecular Docking Studies and Biological Activity

et al. 2023

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The purpose of this work was to prepare new isatin- and monothiomalondiamide-based indole derivatives, as well as to study the properties of the new compounds. The four-component reaction of 5-R-isatins (R = H, CH3), malononitrile, monothiomalonamide (3-amino-3-thioxo- propanamide) and triethylamine in hot EtOH yields a mixture of isomeric triethylammonium 6′-amino-3′-(aminocarbonyl)-5′-cyano-2-oxo-1,2-dihydro-1′H- and 6′-amino-3′-(aminocarbonyl)- 5′-cyano-2-oxo-1,2-dihydro-3′H-spiro[indole-3,4′-pyridine]-2′-thiolates. The reactivity and structure of the products was studied. We found that oxidation of spiro[indole-3,4′-pyridine]-2′-thiolates with DMSO-HCl system produced only acidification products, diastereomeric 6′-amino-5′-cyano-5-methyl-2-oxo-2′-thioxo-1,2,2′,3′-tetrahydro-1′H-spiro-[indole-3,4′-pyridine]- 3′-carboxamides, instead of the expected isothiazolopyridines. The alkylation of the prepared spiro[indole-3,4′-pyridine]-2′-thiolates upon treatment with N-aryl α-chloroacetamides and α-bromoacetophenones proceeds in a regioselective way at the sulfur atom. In the case of α-bromoacetophenones, ring-chain tautomerism was observed for the S-alkylation products. According to NMR data, the compounds consist of a mixture of stereoisomers of 2′-amino-6′-[(2-aryl- 2-oxoethyl)thio]-3′-cyano-2-oxo-1′H-spiro[indoline-3,4′-pyridine]-5′-carboxamides and 5′-amino- 3′-aryl-6′-cyano-3′-hydroxy-2-oxo-2′,3′-dihydrospiro[indoline-3,7′-thiazolo[3,2-a]pyridine]-8′-carboxamides in various ratios. The structure of the synthesized compounds was confirmed by IR spectroscopy, HRMS, 1H and 13C DEPTQ NMR studies and the results of 2D NMR experiments (1H-13C HSQC, 1H-13C HMBC). Molecular docking studies were performed to investigate suitable binding modes of some new compounds with respect to the transcriptional regulator protein PqsR of Pseudomonas aeruginosa. The docking studies revealed that the compounds have affinity for the bacterial regulator protein PqsR of Pseudomonas aeruginosa with a binding energy in the range of −5.8 to −8.2 kcal/mol. In addition, one of the new compounds, 2′-amino-3′-cyano-5-methyl- 2-oxo-6′-{[2-oxo-2-(p-tolylamino)ethyl]thio}-1′H-spiro-[indoline-3,4′-pyridine]-5′-carboxamide, showed in vitro moderate antibacterial effect against Pseudomonas aeruginosa and good antioxidant properties in a test with 1,1-diphenyl-2-picrylhydrazyl radical. Finally, three of the new compounds were recognized as moderately active herbicide safeners with respect to herbicide 2,4-D in the laboratory experiments on sunflower seedlings.

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A Review on The Chemistry of Nicotinonitriles and Their applications

Cited by 14 publications

References 69 publications

Imidazo[1,2,4]triazolone and fused imidazo[1,2,4]triazolone derivatives: Synthesis, in vitro anticancer screening, CDK2 inhibitory activity, and molecular modeling studies

Imidazo[1,2,4]triazolone and fused imidazo[1,2,4]triazolone derivatives: Synthesis, in vitro anticancer screening, CDK2 inhibitory activity, and molecular modeling studies

Synthesis and Some Properties of New 5-Hydroxy-2-[(hetarylthio)methyl]-4H-pyran-4-ones

New 6′-Amino-5′-cyano-2-oxo-1,2-dihydro-1′H-spiro[indole-3,4′-pyridine]-3′-carboxamides: Synthesis, Reactions, Molecular Docking Studies and Biological Activity

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