An Efficient Synthesis of 4‐Naphthylpyrimidin‐2‐amine Derivatives under Solvent‐Free Conditions

Rong, Liangce; Ji, Honglou; Sheng, Xia; Yin, Shou-Wei; Shi, Yanhui; Tu, Shu‐Jiang

doi:10.1002/jhet.839

Cited by 8 publications

(5 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Other binucleophilic reagents such as thiourea and guanidine hydrochloride were permitted to react with chalcone 1 to afford the pyrimidine derivatives 11 and 12 , respectively (Scheme 2). Compound 12 was previously prepared by one pot multicomponent reaction [30] . The FT‐IR‐spectra of the products lacked any carbonyl absorption bands.…”

Section: Resultsmentioning

confidence: 99%

“…Compound 12 was previously prepared by one pot multicomponent reaction. [30] The FT-IRspectra of the products lacked any carbonyl absorption bands. Then, compound 13 was allowed to react with salicylaldehyde, thioglycolic acid, and p-nitro benzaldehyde to afford the hydrazide-hydrazone derivatives 14, 15, and 16, respectively, as shown in Scheme 4.…”

Section: Chemistrymentioning

confidence: 99%

See 1 more Smart Citation

Exploring the Antioxidant Potency of New Naphthalene‐Based Chalcone Derivatives: Design, Synthesis, Antioxidant Evaluation, Docking Study, DFT Calculations

Balamon,

El‐Bordany,

Mahmoud

et al. 2023

Chemistry & Biodiversity

View full text Add to dashboard Cite

A new naphthalene‐based chalcone derivative was successfully synthesized through the condensation of 2,4‐dichlorobenzaldehyde with 2‐acetylnaphthalene. This chalcone, denoted as compound 1, demonstrated a versatile reactivity upon treatment with both nitrogen and carbon nucleophiles, and yielded diverse heterocyclic scaffolds such as pyrazoline, thiazole, pyrimidine, pyran, and pyridine derivatives. The pyrazoline aldehyde derivative 7 was further derivatized to produce the hydrazide‐hydrazone 13, namely, (1H‐pyrazol‐1‐yl)methylene)acetohydrazide, which was exploited to synthesize derivatives of 2‐oxo‐2H‐chromene‐3‐carbohydrazide 14, 2‐(4‐oxo‐4,5‐dihydrothiazol‐2‐yl)acetohydrazide 15, and 3‐(4‐nitrophenyl)acrylohydrazide 16. All the newly synthesized compounds were characterized spectroscopic data. Furthermore, these heterocyclic derivatives were screened for their antioxidant capacities using the DPPH radical assay. The results showed that compounds 5 and 10 are the most potent antioxidants with IC50 comparable to that of ascorbic acid. Meanwhile, compounds 2, 12, 13, 14, 15, and 16 exhibited moderate antioxidant activities. Thus, these heterocycles could emerge as promising antioxidant drugs for the treatment of oxidative stress‐related diseases. Finally, molecular docking was conducted to study the binding affinity for the most potent antioxidant compounds 5, 10, and ascorbic acid inside the active pocket of Human Peroxiredoxin 5. DFT calculations and global descriptors were calculated for the most potent compounds to correlate the relation between chemical structure and reactivity.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Exploring the Antioxidant Potency of New Naphthalene‐Based Chalcone Derivatives: Design, Synthesis, Antioxidant Evaluation, Docking Study, DFT Calculations

Balamon,

El‐Bordany,

Mahmoud

et al. 2023

Chemistry & Biodiversity

View full text Add to dashboard Cite

show abstract

“…Two derivatives, 16 and 20, have been reported to show anticancer activity [8]. Several derivatives were known to show other biological activities: 2, 3, 4, 7 (antibacterial), 14 (nucleoside binding affinity), 19 (anticonvulsant), 23 (antifungal), and 25 (antimicrobial) [4][5][6][7].…”

Section: Synthesismentioning

confidence: 99%

“…1d). Of them, several compounds were reported previously, but the biological activities of some compounds were related with antibacterial, antifungal, and anticonvulsant activities, and the synthetic methods of other compounds were reported [4][5][6][7]. Only derivative 16 was reported to show anticancer activity [8].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and biological evaluation of polyphenols with 4,6-diphenylpyrimidin-2-amine derivatives for inhibition of Aurora kinase A

et al. 2019

View full text Add to dashboard Cite

Background Several 4,6-diarylpyrimidin-2-amine derivatives show anticancer properties. However, their mode of action is not fully characterized. To develop potent anticancer chemotherapeutic agents, we designed and synthesized 25 4,6diphenylpyrimidin-2-amine derivatives containing a guanidine moiety. Methods Clonogenic long-term survival assays were performed to screen anticancer compounds. To derive the structural conditions showing good cytotoxicities against cancer cells, quantitative structure-activity relationships (QSAR) were calculated. Biological activities were determined by flow cytometry for cell cycle analysis and by immunoblot analysis for the detection of Aurora kinase A (AURKA) activity. Because 2-(2-Amino-6-(2,4-dimethoxyphenyl)pyrimidin-4-yl) phenol (derivative 12) selectively inhibited AURKA activity from the kinome assay, in silico docking experiments were performed to elucidate the molecular binding mode between derivative 12 and AURKA. Results The pharmacophores were derived based on the QSAR calculations. Derivative 12 inhibited AURKA activity and reduced phosphorylation of AURKA at Thr283 in HCT116 human colon cancer cells. Derivative 12 caused the accumulation of the G2/M phase of the cell cycle and triggered the cleavages of caspase-3, caspase −7, and poly(ADP-ribose) polymerase. The binding energies of 30 apo-AURKAderivative 12 complexes obtained from in silico docking ranged from −16.72 to −11.63 kcal/mol. Conclusions Derivative 12 is an AURKA inhibitor, which reduces clonogenicity, arrests the cell cycle at the G2/M phase, and induces caspase-mediated apoptotic cell death in HCT116 human colon cancer cells. In silico docking demonstrated that derivative 12 binds to AURKA well. The structure-activity relationship calculations showed hydrophobic substituents and 1naphthalenyl group at the R2 position increased the activity. The existence of an H-bond acceptor at C-2 of the R1 position increased the activity, too.

show abstract

“…In recent years, we have designed and synthesized some kinds heterocyclic compounds , herein, we reported an efficient method for the synthesis of DHPMs‐type compounds by the reactions of aromatic aldehyde, 4,4,4‐trifluoro‐1‐(thien‐2‐yl)butane‐1,3‐dione, and urea under mild conditions.…”

Section: Introductionmentioning

confidence: 99%

An Efficient and Facile Synthesis of 5‐(Thiophene‐2‐carbonyl)‐6‐(trifluoromethyl)‐tetrahydro‐pyrimidin‐2(1H)‐one and 6‐(Thiophen‐2‐yl)‐4,5‐dihydropyrimidin‐2(1H)‐one from Same Substrates Under Different Conditions

Rong

Zha

Sheng

et al. 2014

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

A series of 5‐(thiophene‐2‐carbonyl)‐6‐(trifluoromethyl)‐tetrahydropyrimidin‐2(1H)‐one and 6‐(thiophen‐2‐yl)‐4,5‐dihydropyrimidin‐2(1H)‐one derivatives have been synthesized from the reactions of aromatic aldehydes, 4,4,4‐trifluoro‐1‐(thien‐2‐yl)butane‐1,3‐dione and urea under the different conditions with high yields. In this research, it was found that the p‐toluenesulfonic acid was an efficient catalyst for obtaining 5‐(thiophene‐2‐carbonyl)‐6‐(trifluoromethyl)‐tetrahydropyrimidin‐2(1H)‐one derivative. At the same time, solvent‐free and NaOH were the preferred conditions for the synthesis of 6‐(thiophen‐2‐yl)‐4,5‐dihydropyrimidin‐2(1H)‐one derivative. Moreover, because of short reaction time, excellent yields, simple setup, this research offered an efficient process for preparing these kind compounds.

show abstract

An Efficient Synthesis of 4‐Naphthylpyrimidin‐2‐amine Derivatives under Solvent‐Free Conditions

Cited by 8 publications

References 19 publications

Exploring the Antioxidant Potency of New Naphthalene‐Based Chalcone Derivatives: Design, Synthesis, Antioxidant Evaluation, Docking Study, DFT Calculations

Exploring the Antioxidant Potency of New Naphthalene‐Based Chalcone Derivatives: Design, Synthesis, Antioxidant Evaluation, Docking Study, DFT Calculations

Design, synthesis, and biological evaluation of polyphenols with 4,6-diphenylpyrimidin-2-amine derivatives for inhibition of Aurora kinase A

An Efficient and Facile Synthesis of 5‐(Thiophene‐2‐carbonyl)‐6‐(trifluoromethyl)‐tetrahydro‐pyrimidin‐2(1H)‐one and 6‐(Thiophen‐2‐yl)‐4,5‐dihydropyrimidin‐2(1H)‐one from Same Substrates Under Different Conditions

Contact Info

Product

Resources

About