Synthesis of a series of carbon-14 labeled tetrahydropyrido[4,3-d]pyrimidin-4(3H)-ones

Arjomandi, Omid Khalili; Saemian, Nader; McGeary, Ross P.; Shirvani, Gholamhossein

doi:10.1002/jlcr.3110

Cited by 3 publications

(2 citation statements)

References 21 publications

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“…Also, the other key intermediates 5a – 5o were prepared from R-substituted nitriles ( 4a – 4o ) under two different methods that both were Pinner reactions and complemented each other. Compounds 5g – 5o were achieved by the Pinner reaction that used sodium methoxide as the catalyst, while the classical one catalyzed by hydrogen chloride was used to afford compounds 5a – 5f for higher yields . Then, in the presence of freshly made sodium methoxide, intermediates 6a – 6o were obtained from the mixture of 3 and 5a – 4o at room temperature, followed by reacting with POCl 3 that also served as a solvent to give 7a – 7o .…”

Section: Results and Discussionmentioning

confidence: 99%

Novel Allosteric Inhibitors of Deoxyhypusine Synthase against Malignant Melanoma: Design, Synthesis, and Biological Evaluation

Liu

Wang

et al. 2021

J. Med. Chem.

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Based on the novel allosteric site of deoxyhypusine synthase (DHPS), two series of 30 novel 5-(2-methoxyphenoxy)-2-phenylpyrimidin-4-amine derivatives as DHPS inhibitors were designed and synthesized. Among them, compound 8m, with the best DHPS inhibitory potency (IC 50 = 0.014 μM), exhibited excellent inhibition against melanoma cells, which was superior to that of GC7. Besides, molecular docking and molecular dynamics (MD) simulations further proved that compound 8m was tightly bound to the allosteric site of DHPS. Flow cytometric analysis and enzyme-linked immunosorbent assay (ELISA) showed that compound 8m could inhibit the intracellular reactive oxygen species (ROS) level. Furthermore, by western blot analysis, compound 8m effectively activated caspase 3 and decreased the expressions of GP-100, tyrosinase, eIF5A2, MMP2, and MMP9. Moreover, both Transwell analysis and wound healing analysis showed that compound 8m could inhibit the invasion and migration of melanoma cells. In the in vivo study, the tumor xenograft model showed that compound 8m effectively inhibited melanoma development with low toxicity.

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Section: Results and Discussionmentioning

confidence: 99%

Novel Allosteric Inhibitors of Deoxyhypusine Synthase against Malignant Melanoma: Design, Synthesis, and Biological Evaluation

Liu

Wang

et al. 2021

J. Med. Chem.

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“…The reactions were monitored by thin-layer chromatography (TLC). 2bromoacetyl-ferrocene 40 , 1,2-bis(ferrocenecarbonyl)hydrazine 41,42 , ferrocenecarbonyl-hydrazine 43 , N-(Ferrocenecarbonylmethyl)ferrocenecarboxamide 44 , ferroceneamidine 45,46 and cyanoferrocene 47 were prepared according to literature methods, and the solvents were commercially available. The 1-3 synthetic method have been report in our previous work 31 .…”

Section: Methodsmentioning

confidence: 99%

The Intramolecular Electronic Interaction Regulated by Five-membered Heterocycle Spacer

Han

Wang

2021

Preprint

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The spacer in diferrocenyl derivatives has significant effects on intramolecular electronic interaction properties. In this work, nine diferrocenyl five-membered heterocyclic molecules are synthesized as models to investigate the effect of intramolecular electron-transfer properties systematically, including 2,5-diferrocenyl-1-phenyl-pyrrole (1), 2,5-diferrocenylfuran (2), 2,5-diferrocenylthiophene (3), 2,5-diferrocenyl-1H-imidazole (4), 2,5-diferrocenyloxazole (5), 2,5-diferrocenylthiazole (6), 2,5-diferrocenyl-1,3,4-triazole (7), 2,5-diferrocenyl-1,3,4-oxadiazole (8) and 2,5-diferrocenyl-1,3,4-thiadiazole (9). The molecules were prepared in cyclization reaction and characterized by Elemental analysis, FT-IR, MS and NMR. Moreover, the molecular structures of 2,5-diferrocenylthiazole and 2,5-diferrocenyl-1,3,4-oxadiazole were determined by the single crystal X-ray diffraction. The intramolecular electronic interactions were investigated through cyclic voltammetry in combination with density functional theory (DFT) calculations. The results revealed that the electronic interaction decreased with the increase of heteroatoms in central heterocycle spacer, and the electron-transfer property could be regulated by regulate central heterocycle spacer species.

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Synthesis of deuterium labeled dabigatran etexilate

He,

Li,

Sun

et al. 2024

J Radioanal Nucl Chem

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Synthesis of a series of carbon-14 labeled tetrahydropyrido[4,3-d]pyrimidin-4(3H)-ones

Abstract: A series of tetrahydropyrido[4,3-d]pyrimidin-4(3H)-ones labeled with carbon-14 in the 2-position of pyrimidinone moiety were prepared as part of a 3-step sequence from benz[amidino-(14) C]amidine hydrochloride as a key synthetic intermediate.

Cited by 3 publications

References 21 publications

Novel Allosteric Inhibitors of Deoxyhypusine Synthase against Malignant Melanoma: Design, Synthesis, and Biological Evaluation

Novel Allosteric Inhibitors of Deoxyhypusine Synthase against Malignant Melanoma: Design, Synthesis, and Biological Evaluation

The Intramolecular Electronic Interaction Regulated by Five-membered Heterocycle Spacer

Synthesis of deuterium labeled dabigatran etexilate

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