Novel quinolines and pyrimido[4,5-b]quinolines bearing biologically active sulfonamide moiety as a new class of antitumor agents

Alqasoumi, Saleh I.; Al‐Taweel, Areej Mohammad; Alafeefy, Ahmed M.; Noaman, Eman; Ghorab, Mostafa M.

doi:10.1016/j.ejmech.2009.11.021

Cited by 115 publications

(60 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…• pulse width = 14 µs, 13 pulse width = 8.5 µs) at room temperature with standard Bruker pulse programs. The samples were dissolved in 0.6 ml of CDCl 3 .…”

Section: Methodsmentioning

confidence: 99%

“…An average 1 J(C, H) of 145 Hz was used. 1 H, 13 C long-range spectra HMBC (hmbcgplpndqf ) were acquired with the same D 16 (200 µs), P 16 (1.5 ms) and 5 : 3 : 4 gradient combination using a pulse sequence optimized for 8 Hz. Melting points were measured on an electrothermal melting point apparatus and are uncorrected.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR data were collected with 64K complex data points and were apodized with an exponential window function (lb = 0.3) prior to Fourier transformation. 13 C-jmod spectra with WALTZ16 1 H decoupling were acquired using 64K data points. Signal-to-noise enhancement was achieved by multiplication of the FID with an exponential window function (lb = 1 Hz).…”

Section: Methodsmentioning

confidence: 99%

“…In addition, the remaining high-frequency signal at δ C = 162.0 ppm was assignable to the conjugated carbonyl (C4), while the other one at δ C = 153.6 ppm was attributed to C2. These assignments of the two quaternary carbons without any HMBC correlations were further attested by the comparison of the 13 Table 1.…”

Section: Nmr Spectroscopic Investigationsmentioning

confidence: 98%

See 3 more Smart Citations

Synthesis and structure elucidation of five new pyrimido[5,4‐c]quinoline‐4(3H)‐one derivatives using 1D and 2D NMR spectroscopy

Yang

Liu

et al. 2010

Magnetic Reson in Chemistry

View full text Add to dashboard Cite

show abstract

“…• pulse width = 14 µs, 13 pulse width = 8.5 µs) at room temperature with standard Bruker pulse programs. The samples were dissolved in 0.6 ml of CDCl 3 .…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Nmr Spectroscopic Investigationsmentioning

confidence: 98%

See 2 more Smart Citations

Synthesis and structure elucidation of five new pyrimido[5,4‐c]quinoline‐4(3H)‐one derivatives using 1D and 2D NMR spectroscopy

Yang

Liu

et al. 2010

Magnetic Reson in Chemistry

View full text Add to dashboard Cite

show abstract

“…Also, several novel quinoline derivatives have been reported to show substantial anticancer activities [7][8][9][10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of some novel quinoline derivatives as anticancer and radiosensitizing agents targeting VEGFR tyrosine kinase

Ghorab

Ragab

Heiba

et al. 2011

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

in Wiley Online Library (wileyonlinelibrary.com).Quinoline derivatives posses many types of biological activities and have been reported to show significant anticancer activity. There is a variety of mechanisms for the anticancer activity and the most distinguished mechanism is the inhibition of vascular epithelial growth factor receptor tyrosine kinase (VEGFRTK). Novel quinoline derivatives 6-12 and pyrimido [4,5-b]quinoline derivatives 16-20 are reported herein. All the newly synthesized compounds were evaluated for their in vitro anticancer activity against human breast cancer cell line (MCF7) in which VEGFR is highly expressed. Compounds 6 and 7 with IC 50 values of 8.5 lM and 21.9 lM were the most active compounds and exhibited cytotoxic activities higher than that of the reference drug doxorubicin (IC 50 ¼ 32.02 lM). The most active compounds 6 and 7 were further evaluated for their ability to enhance the cell killing effect of c-radiation.

show abstract

Synthesis of novel pyrimido[4,5‐b]quinoline derivatives as dual EGFR/HER2 inhibitors as anticancer agents

Ibrahim,

Kadry,

Zaher

et al. 2023

Archiv der Pharmazie

View full text Add to dashboard Cite

A series of novel N‐aryl‐5‐aryl‐6,7,8,9‐tetrahydropyrimido[4,5‐b]quinolin‐4‐amines 4a–4l was synthesized as potential anticancer agents through Dimroth rearrangement reaction of intermediates 3a–3c. Pyrimido[4,5‐b]quinolines 4a–4l showed promising activity against the Michigan Cancer Foundation‐7 (MCF‐7) cell line, compared with lapatinib as the reference drug. Compounds 4d, 4h, 4i, and 4l demonstrated higher cytotoxic activity than lapatinib, with IC50 values of 2.67, 6.82, 4.31, and 1.62 µM, respectively. Compounds 4d, 4i, and 4l showed promising epidermal growth factor receptor (EGFR) inhibition with IC50 values of 0.065, 0.116, and 0.052 µM, respectively. These compounds were subjected to human epidermal growth factor receptor 2 (HER2) inhibition and showed IC50 values of 0.09, 0.164, and 0.055 µM, respectively. Compounds 4d, 4i, and 4l are good candidates as dual EGFR/HER2 inhibitors. The most active compound, 4l, was subjected to cell‐cycle analysis and induced cell‐cycle arrest at the S phase. Compound 4l induced apoptosis 60‐fold compared with control untreated MCF‐7 cells. 4l can inhibit cancer metastasis. It reduced MCF‐7 cell infiltration and metastasis by 45% compared with control untreated cells.

show abstract

Novel quinolines and pyrimido[4,5-b]quinolines bearing biologically active sulfonamide moiety as a new class of antitumor agents

Cited by 115 publications

References 23 publications

Synthesis and structure elucidation of five new pyrimido[5,4‐c]quinoline‐4(3H)‐one derivatives using 1D and 2D NMR spectroscopy

Synthesis and structure elucidation of five new pyrimido[5,4‐c]quinoline‐4(3H)‐one derivatives using 1D and 2D NMR spectroscopy

Design and synthesis of some novel quinoline derivatives as anticancer and radiosensitizing agents targeting VEGFR tyrosine kinase

Synthesis of novel pyrimido[4,5‐b]quinoline derivatives as dual EGFR/HER2 inhibitors as anticancer agents

Contact Info

Product

Resources

About