Synthesis and biological evaluation of 1-phenyl-4,6-dihydrobenzo[b]pyrazolo[3,4-d]azepin-5(1H)-one/thiones as anticancer agents

Parupalli, Ramulu; Akunuri, Ravikumar; Spandana, Akella; Phanindranath, Regur; Pyreddy, Suneela; Bazaz, Mohd Rabi; Vadakattu, Manasa; Joshi, Swanand Vinayak; Bujji, Sushmitha; Balakishan, Gorre; Yaddanapudi, Venkata Madhavi; Dandekar, Manoj P.; Reddy, Velma Ganga; Nagesh, Narayana; Nanduri, Srinivas

doi:10.1016/j.bioorg.2023.106478

Cited by 13 publications

(4 citation statements)

References 57 publications

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“…Trypsinization was used to collect the cells, which were washed twice with PBS before being resuspended in PBS and stained with 5 mL of Annexin V‐FITC and 5 mL of PI in 1x binding buffer for 15 min at room temperature in the dark. The FITC signal detector (FL1) of a BD FACS Calibur flow cytometer (Ex = 488 nm; Em = 530 nm) was used to examine the annexin V‐FITC binding, and the phycoerythrin emission signal detector was used to analyze the PI staining (FL2; Parupalli et al, 2023).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of novel pyrimido[4,5‐b]quinolines as potential anticancer agents and HER2 inhibitors

Ibrahim,

Kadry,

Zaher

et al. 2023

Chem Biol Drug Des

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A series of N‐arylpyrimido[4,5‐b]quinolines 3a–e and 2‐aryl‐2,3‐dihydropyrimido[4,5‐b]quinoline‐4(1H)‐ones 5a–e was designed and synthesized as potential anticancer agents against breast cancer. Compounds 3e, 5a, 5b, 5d, and 5e showed promising activity against the MCF‐7 cell line. Among them, compound 5b was the most active with IC50 of 1.67 μM. Compound 5b promoted apoptosis and induced cell cycle arrest at S phase. 5b increased the level of pro‐apoptotic proteins p53, Bax, and caspase‐7 and inhibited the anti‐apoptotic protein Bcl‐2. Furthermore, all the synthesized compounds were docked into the crystal structure of HER2 (PBD: 3 pp0). Compounds 3e, 5a, 5b, 5d, and 5e showed good energy scores and binding modes. Finally, Compound 5b was evaluated on the HER2 assay and revealed good inhibition with IC50 of 0.073 μM.

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Section: Methodsmentioning

confidence: 99%

Synthesis of novel pyrimido[4,5‐b]quinolines as potential anticancer agents and HER2 inhibitors

Ibrahim,

Kadry,

Zaher

et al. 2023

Chem Biol Drug Des

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show abstract

“…Cell pellets were re-suspended in ice-cold 1× binding buffer, to which 1 μL of annexin V-FITC solution and 5 μL PI (propidium iodide) was added. 35 400 μL of ice-cold 1× binding buffer was poured to tubes that had been placed on ice and allowed to sit in the dark for 15 min. Using a BD AccuriTM C5 flow cytometer (BD Biosciences, CA, USA), cell preparations were examined.…”

Section: Apoptosismentioning

confidence: 99%

Design, in silico studies, synthesis, and in vitro anticancer assessment of new naphthylidene isoxazolidinedione derivatives

Upadhyay,

Tilekar,

Oak

et al. 2024

Vietnam Journal of Chemistry

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Cancer is the most destructive and fatal disease, representing an urgent medical challenge to the world. The discovery of a new anticancer candidate may help reduce or eliminate this alarming disease to a greater extent. On similar lines, in silico research was carried out on novel naphthylidene isoxazolidinedione derivatives that were logically conceived, synthesized, purified, and structurally characterized. In vitro biological evaluation revealed the most active compound 4d with an inhibitory concentration of 42.87 µm against K562 and 47.42 µm on A549 cells. The anticancer activity of this naphthylidene isoxazolidinedione derivative was evident by cell cycle and apoptosis assays, which showed arrest of the G2/M phase (65.6%) of the K562 cells and induction of apoptosis with 21.47% apoptotic cells as compared to 0.2% of untreated cells, respectively.

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“…After incubation, the annexin V-FITC binding was examined using FITC signal detector and was used to examine and the PI staining using phycoerythrin emission signal detector. [57]…”

Section: Apoptosis Analysis By Flowcytometrymentioning

confidence: 99%

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

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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.

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Synthesis and biological evaluation of 1-phenyl-4,6-dihydrobenzo[b]pyrazolo[3,4-d]azepin-5(1H)-one/thiones as anticancer agents

Cited by 13 publications

References 57 publications

Synthesis of novel pyrimido[4,5‐b]quinolines as potential anticancer agents and HER2 inhibitors

Synthesis of novel pyrimido[4,5‐b]quinolines as potential anticancer agents and HER2 inhibitors

Design, in silico studies, synthesis, and in vitro anticancer assessment of new naphthylidene isoxazolidinedione derivatives

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

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