Design, synthesis, biological activities and 3D-QSAR studies of quinazolinone derivatives containing hydrazone structural units

Shao, Lihui; Fan, Sili; Meng, Ying-Fen; Gan, Yi‐Yuan; Shao, Wu-Bin; Wang, Zhenchao; Chen, Danping; Ouyang, Gangfeng

doi:10.1039/d0nj05450j

Cited by 12 publications

(4 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1 g; 68% yield; 1 H NMR (DMSO, 400 MHz), δ 9.90 (s, 1H), 8.16 (dd, J = 8.0, 1.0 Hz, 1H), 7.90 (d, J = 8.8 Hz, 2H), 7.82 (ddd, J = 8.4, 7.2, 1.6 Hz, 1H), 7.63 (d, J = 7.6 Hz, 1H), 7.60–7.52 (m, 1H), 7.32 (d, J = 8.8 Hz, 2H), 5.45 (s, 2H), 3.62 (s, 3H). Spectral properties were in accordance with the literature 23 .…”

Section: Methodssupporting

confidence: 81%

“…1.04 g; 50% yield; 1 H NMR (400 MHz, CDCl 3 ) d 8.29 (d, J ¼ 8.0 Hz, 1H), 7.80 À 7.75 (m, 1H), 7.68 À 7.69 (m, 1H), 7.50 À 7.54 (m, 1H), 4.65 (s, 2H), 3.76 (s, 3H). Spectral properties were in accordance with the literature 23 .…”

Section: Synthesissupporting

confidence: 81%

“…The synthetic route was shown in Scheme 1 . At first, compound 2 and 3 were prepared under the described conditions in literature 23 . And then, compound 3 experienced in aldol-condensation with 3-fluorophenylethanone to give the product 4a .…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

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

View full text Add to dashboard Cite

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.

show abstract

Section: Methodssupporting

confidence: 81%

Section: Synthesissupporting

confidence: 81%

See 1 more Smart Citation

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

View full text Add to dashboard Cite

show abstract

“…Compound D31 was used as the template molecule (Table S1). The most reliable 3D-QSAR models were obtained using a partial least-squares analysis (PLS) regression approach …”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, Antibacterial Evaluation, Three-Dimensional Quantitative Structure–Activity Relationship, and Mechanism of Novel Quinazolinone Derivatives

Shao

Zhao

Yang

et al. 2023

J. Agric. Food Chem.

Self Cite

View full text Add to dashboard Cite

Plant bacterial illnesses are common and cause dramatic damage to agricultural goods all over the world, yet there are few efficient bactericides to alleviate them at present. To discover novel antibacterial agents, two series of quinazolinone derivatives with novel structures were synthesized and their bioactivity against plant bacteria was tested. Combining CoMFA model search and the antibacterial bioactivity assay, D32 was identified as a potent antibacterial inhibitor against Xanthomonas oryzae pv. Oryzae (Xoo), with an EC 50 value of 1.5 μg/mL, much better in inhibitory capacity compared to bismerthiazol (BT) and thiodiazole copper (TC) (31.9 and 74.2 μg/mL). The activities of compound D32 against rice bacterial leaf blight in vivo were 46.7% (protective activities) and 43.9% (curative activities), better than commercial drug thiodiazole copper (29.3% protective activities and 30.6% curative activities). Flow cytometry, proteomics, reactive oxygen species, and key defense enzymes were used to further investigate the relevant mechanisms of action of D32. The identification of D32 as an antibacterial inhibitor and revelation of its recognition mechanism not only open the possibility of developing new therapeutic strategies for treatment of Xoo but also provide clues for elucidation of the acting mechanism of quinazolinone derivative D32, which is a possible clinical candidate worth in-depth study.

show abstract

Design and synthesis of novel quinazolinyl-bisspirooxindoles as potent anti-tubercular agents: an ultrasound-promoted methodology

et al. 2022

View full text Add to dashboard Cite

Design, synthesis, biological activities and 3D-QSAR studies of quinazolinone derivatives containing hydrazone structural units

Abstract: In this letter, three series of quinazolinone derivatives containing hydrazone structure were designed and synthesized. Bioactivity assays indicated that these compounds showed good antitumour activities toward human lung cancer cells...

Cited by 12 publications

References 27 publications

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

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

Design, Synthesis, Antibacterial Evaluation, Three-Dimensional Quantitative Structure–Activity Relationship, and Mechanism of Novel Quinazolinone Derivatives

Design and synthesis of novel quinazolinyl-bisspirooxindoles as potent anti-tubercular agents: an ultrasound-promoted methodology

Contact Info

Product

Resources

About