Microwave-assisted synthesis of phenylpyrimidine derivatives via Suzuki-Miyaura reactions in water

Le, Yi; Zhang, Yan; Wang, Qin; Rao, Nian; Li, Dan; Liu, Li; Ouyang, Gangfeng; Yan, Longjia

doi:10.1016/j.tetlet.2021.152903

Cited by 17 publications

(10 citation statements)

References 28 publications

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“…These compounds can be used to construct 2-aminothiophene compounds library and as intermediates to develop new drugs. All the compounds were confirmed by 1 H NMR, 13 C NMR and MS. Further studies of these compounds are still ongoing in our lab.…”

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confidence: 83%

“…It has been proved that microwave-assisted synthesis can greatly increase the reaction rate and reduce the formation of by-products. [13][14][15] In 2007, Sridhar firstly reported the microwave-assisted Gewald reaction for the synthesis of 2-aminothiophene. 16 However, there are still some drawbacks for this procedure including limit of substrates and moderate yield.…”

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confidence: 99%

“…Therefore, pyrrolidine was regarded as the optimal base of the model reaction. Then we screened the different solvents including DMSO, EtOH, i-PrOH, THF, dioxane, DCM, NMP, toluene, MeCN (Table 1, entries [11][12][13][14][15][16][17][18][19].…”

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confidence: 99%

“…IR spectra were measured on Bio-Rad FTS spectrophotometer. 1 H NMR and 13 C NMR spectra were measured on a Bruker (Avance) 400 MHz NMR instrument in DMSO-d6 with chemical shift (δ) given in parts per million (ppm) relative to TMS as internal standard and recorded at 23 °C. The mass spectra were recorded using a liquid-mass spectrometer.…”

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confidence: 99%

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Microwave-Assisted Synthesis of 2-Aminothiophene Derivatives via Improved Gewald Reactions

Li¹,

Ruan²,

Zhang³

et al. 2021

HETEROCYCLES

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In this paper, a new and efficient method was developed to prepare 2-aminothiophene derivatives through improved Gewald reaction. Thirty-one final products were synthesized under microwave radiation for 30 min with 57%-95% isolated yields. All the products could be used as building blocks in drug discovery.2-Aminothiophenes are important organic intermediates, which are often found in drug research. 1,2 Due to the broad activities of the derivatives including anti-microbial, anti-tumor, anti-oxidation, and anti-inflammatory, it has been greatly interested in development of new 2-aminothiophenes for organic chemists and medicinal chemists. [3][4][5] In 2013, Davis reported a new drug candidate CaCCinh-A01, 6 which was used as inhibitor for treatment of glioblastoma. In addition, Ballatore studied ATTZ-15 and 2-TCU 7 in the next year, which were performed significant effects in neurological diseases. Recently, Sim also developed a series of 2-aminothiophene-3-carboxamide derivatives as calcium-activated chloride ion channel blockers. 8

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confidence: 83%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Microwave-Assisted Synthesis of 2-Aminothiophene Derivatives via Improved Gewald Reactions

Li¹,

Ruan²,

Zhang³

et al. 2021

HETEROCYCLES

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“…Our group has been focussed on the research of developing new anti-tumour drugs for several years [16][17][18][19] . We have synthesised lots of antiproliferative compounds such as benzodiazepines, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles 20 , and pyrimidines 21 . Based on the broad activities of quinazolone and imperative need for EGFR inhibitors, we reported a series of 3-methylquinazolone derivatives for EGFR inhibitors in last year 22 .…”

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confidence: 99%

Synthesis and preliminary structure-activity relationship study of 3-methylquinazolinone derivatives as EGFR inhibitors with enhanced antiproliferative activities against tumour cells

Zhang

Wang

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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In this paper, a set of 3-methylquniazolinone derivatives were designed, synthesised, and studied the preliminary structure-activity relationship for antiproliferative activities. All target compounds performed significantly inhibitory effects against wild type epidermal growth factor receptor tyrosine kinase (EGFR wt -TK) and tumour cells (A431, A549, MCF-7, and NCI-H1975). In particular, compound 4d 3-fluoro- N -(4-((3-methyl-4-oxo-3,4-dihydroquinazolin-2-yl)methoxy)phenyl)benzamide showed higher antiproliferative activities against all tumour cells than Gefitinib (IC 50 of 3.48, 2.55, 0.87 and 6.42 μM, respectively). Furthermore, compound 4d could induce apoptosis of MCF-7 cells and arrest in G2/M phase at the tested concentration. Molecular docking and ADMET studies showed that compound 4d could closely form many hydrogen bonds with EGFR wt -TK. Therefore, compound 4d is potential to develop as novel anti-cancer drug.

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A comprehensive review: medicinal applications and diverse synthetic strategies of pyrimidine-based compounds leveraging Suzuki and Sonogashira reactions

Rezaeifard,

Bakherad,

Navidpour

et al. 2024

Monatsh Chem

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Microwave-assisted synthesis of phenylpyrimidine derivatives via Suzuki-Miyaura reactions in water

Cited by 17 publications

References 28 publications

Microwave-Assisted Synthesis of 2-Aminothiophene Derivatives via Improved Gewald Reactions

Microwave-Assisted Synthesis of 2-Aminothiophene Derivatives via Improved Gewald Reactions

Synthesis and preliminary structure-activity relationship study of 3-methylquinazolinone derivatives as EGFR inhibitors with enhanced antiproliferative activities against tumour cells

A comprehensive review: medicinal applications and diverse synthetic strategies of pyrimidine-based compounds leveraging Suzuki and Sonogashira reactions

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