Design, synthesis, and biological evaluation of 4‐aminopyrimidine or 4,6‐diaminopyrimidine derivatives as beta amyloid cleaving enzyme‐1 inhibitors

Xu, Xiufeng; Lü, Peng; Wang, Junjie; Xu, Fengrong; Liu, Liang; Wang, Chao; Niu, Yan; Xu, Ping

doi:10.1111/cbdd.13489

Cited by 7 publications

(8 citation statements)

References 28 publications

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“…In a very recent study, Xu et al studied the BACE1 activity of 4‐amino‐5‐cyano‐pyrimidine compounds, and they found at least three derivatives, which were very similar to our scaffolds, had very strong BACE1 inhibition effects with very low IC 50 levels. For this purpose, we study herein the anti‐ChE activity of bis(4‐amino‐5‐cyanopyrimidine) derivatives.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, molecular docking studies, and biological evaluation of novel alkyl bis(4‐amino‐5‐cyanopyrimidine) derivatives

Boualia

Derabli

Boulcina

et al. 2019

Archiv der Pharmazie

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A series of bis(4-amino-5-cyano-pyrimidines) was synthesized and evaluated as dual inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). To further explore the multifunctional properties of the new derivatives, their antioxidant and antibacterial activities were also tested. The results showed that most of these compounds could effectively inhibit AChE and BChE. Particularly, compound 7c exhibited the best AChE inhibitory activity (IC 50 = 5.72 ± 1.53 μM),whereas compound 7h was identified as the most potent BChE inhibitor (IC 50 = 12.19 ± 0.57 μM). Molecular modeling study revealed that compounds 7c, 7f, and 7b showed a higher inhibitory activity than that of galantamine against both AChE and BChE. Anticholinesterase activity of compounds 7h, 7b, and 7c was significant in vitro and in silico for both enzymes, since these compounds have hydrophobic rings (Brphenyl, dimethyl, and methoxyphenyl), which bind very well in both sites. In addition to cholinesterase inhibitory activities, these compounds showed different levels of antioxidant activities. Indeed, in the superoxide-dimethyl sulfoxide alkaline assay, compound 7j showed very high inhibition (IC 50 = 0.37 ± 0.28 μM). Also, compound 7l exhibited strong and good antibacterial activity against Staphylococcus epidermidis and Staphylococcus aureus, respectively. Taking into account the results of biological evaluation, further modifications will be designed to increase potency on different targets. In this study, the obtained results can be a new starting point for further development of multifunctional agents for the treatment of Alzheimer's disease. K E Y W O R D Salkyl bis(4-amino-5-cyano-pyrimidines), antibacterial activity, anticholinesterase activity, antioxidant effect, molecular docking studies

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Section: Resultsmentioning

confidence: 99%

Synthesis, molecular docking studies, and biological evaluation of novel alkyl bis(4‐amino‐5‐cyanopyrimidine) derivatives

Boualia

Derabli

Boulcina

et al. 2019

Archiv der Pharmazie

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“…13 (23). 32 It was obtained as a white crystal (167.2 mg, 95%), mp 145.5−147.0 °C. Column chromatography eluent, EtOAc/hexane gradient from 1:9 to 3:2.…”

Section: (S)-5-decyl-n-(1-phenylethyl)thiazol-2-amine (20) It Was Obt...mentioning

confidence: 99%

Microwave-Assisted One-Pot Telescoped Synthesis of 2-Amino-1,3-thiazoles, Selenazoles, Imidazo[1,2-a]pyridines, and Other Heterocycles from Alcohols

Macías-Benítez,

Sierra-Padilla,

Guerra

et al. 2024

J. Org. Chem.

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Primary and secondary alcohols have been converted into 2-amino-1,3-thiazoles under microwave irradiation, employing trichloroisocyanuric acid (TCCA) as a dual oxidant and chlorine source, TEMPO as a co-oxidant, and thiourea. Secondary alcohols underwent a single-stage, one-pot conversion process, while primary alcohols required a two-stage, one-pot procedure. Both transformations were completed within minutes (25−45 min). The versatility of this protocol extends to the synthesis of other heterocycles, including 1,3-selenazoles, 2-aminoimidazoles, imidazo[1,2-a]pyridines, quinoxalines, and hydrazino thiazoles by replacing thiourea with the appropriate surrogates.

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“…Because of the basic nitrogen, each compound was formed as HBr salt. Compounds were used as HBr salt in the next step [16].…”

Section: Synthesis Of 2-bromoacetylpyridines (1a-c)mentioning

confidence: 99%

Synthesis, antioxidant and antimicrobial properties of novel pyridyl-carbonyl thiazoles as dendrodoine analogs

Şahin¹,

Biltekin²,

Yurttaş³

et al. 2020

Turk J Chem

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Marine compound dendrodoine was first obtained from tunicate species ( Dendrodo grossularia ). It has a five-membered ring, namely, it is a heterocycle thiadiazole, which is found rarely in natural sources . Following its biological activities, novel analogs have been investigated recently. Synthesis of the analogs for this study is realized with uncommon thiazole closure, including methylene-carbonyl condensation. Structures are elucidated by NMR ( 1 , 13 C) and HRMS spectrums. As an alkaloid derivative, antioxidant properties were evaluated with DPPH and FRAP assays and antimicrobial effect with microdilution method. Among the series, 3bc-3cf showed higher antioxidant activity than those having 3 or 4-pyridyl substituents. There is lesser activity for 2-pyridyl activity for 2-pyridyl containing group, which may be a result of intramolecular interactions. No activity was observed against gram-negative bacteria at 250 μg/mL. 3ae and 3ce showed activity at 64 μg/mL against S. aureus and 3ae showed activity at 16 μg/mL against S. epidermidis gram-positive bacteria. Chloramphenicol showed activity against all microorganisms at 8–16 μg/mL. Sixteen original dendrodoine analogs have been defined by close/higher activity compared to dendrodoine analogs and Trolox.

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Design, synthesis, and biological evaluation of 4‐aminopyrimidine or 4,6‐diaminopyrimidine derivatives as beta amyloid cleaving enzyme‐1 inhibitors

Cited by 7 publications

References 28 publications

Synthesis, molecular docking studies, and biological evaluation of novel alkyl bis(4‐amino‐5‐cyanopyrimidine) derivatives

Synthesis, molecular docking studies, and biological evaluation of novel alkyl bis(4‐amino‐5‐cyanopyrimidine) derivatives

Microwave-Assisted One-Pot Telescoped Synthesis of 2-Amino-1,3-thiazoles, Selenazoles, Imidazo[1,2-a]pyridines, and Other Heterocycles from Alcohols

Synthesis, antioxidant and antimicrobial properties of novel pyridyl-carbonyl thiazoles as dendrodoine analogs

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