Design, synthesis and biological evaluation of 7–(5–((substituted – amino)-methyl)-thiophen–2–yl)-spiro-[chroman–2,4′–piperidin]–4–one hydrochloride analogues as anticancer agents

Chitti, Surendar; Pulya, Sravani; Nandikolla, Adinarayana; Patel, Tarun; Kumar, Banoth Karan; Murugesan, Sankaranarayanan; Ghosh, Balaram; Sekhar, Kondapalli Venkata Gowri Chandra

doi:10.1016/j.bioorg.2021.104865

Cited by 10 publications

(4 citation statements)

References 28 publications

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“…Chitti et al obtained novel 7-(5-((substituted-amino)-methyl)-thiophen-2-yl)-spiro[chroman-2,4′-piperidin]-4-one hydrochloride analogues [ 103 ]. The spirochromanone core was selected on the basis of previously reported derivatives [ 104 ].…”

Section: The Most Potent Anti-melanoma Agent From Most Recent Studies...mentioning

confidence: 99%

“…The proposed compound was the only one to have a simple methylamine moiety; the remaining compounds had longer and more branched or cyclic chains. This may indicate that the methylamine group was crucial for the selectivity of spirochromanone derivatives for melanoma cell line B16F10 [ 103 ].…”

Section: The Most Potent Anti-melanoma Agent From Most Recent Studies...mentioning

confidence: 99%

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New Potential Agents for Malignant Melanoma Treatment—Most Recent Studies 2020–2022

Kozyra

Krasowska

Pitucha

2022

IJMS

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Malignant melanoma (MM) is the most lethal skin cancer. Despite a 4% reduction in mortality over the past few years, an increasing number of new diagnosed cases appear each year. Long-term therapy and the development of resistance to the drugs used drive the search for more and more new agents with anti-melanoma activity. This review focuses on the most recent synthesized anti-melanoma agents from 2020–2022. For selected agents, apart from the analysis of biological activity, the structure–activity relationship (SAR) is also discussed. To the best of our knowledge, the following literature review delivers the latest achievements in the field of new anti-melanoma agents.

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Section: The Most Potent Anti-melanoma Agent From Most Recent Studies...mentioning

confidence: 99%

Section: The Most Potent Anti-melanoma Agent From Most Recent Studies...mentioning

confidence: 99%

New Potential Agents for Malignant Melanoma Treatment—Most Recent Studies 2020–2022

Kozyra

Krasowska

Pitucha

2022

IJMS

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“…They are used as versatile intermediates for the synthesis of many natural products [14][15][16][17][18][19] and constitute interesting building blocks in drug design and organic synthesis [20][21][22][23]. They also exhibit significant biological activities allowing their use as anticancer [24][25][26][27], antifungal and antibacterial [28][29][30][31], anti-inflammatory [32,33], antidiabetic [34,35], anti-leishmanial (caused by protozoan parasites) [36,37], and insecticidal agents [38] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds

et al. 2022

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A novel series of 14 spiropyrrolidines bearing thiochroman-4-one/chroman-4-one, and oxindole/acenaphthylene-1,2-dione moieties were synthesized and characterized by spectroscopic techniques, as well as by three X-ray diffraction studies, corroborating the stereochemistry. Quantum chemical calculations studies, using the DFT approach, were performed to rationalize the stereochemical outcome. These N-heterocycles were evaluated for their antibacterial and antifungal activities against some pathogenic organisms. Several compounds displayed moderate to excellent activity towards the screened microbe strains in the study compared to Amoxicillin (AMX), Ampicillin (AMP), and Amphotericin B. Furthermore, a structural activity relationship (SAR) was established considering the synthesized compounds. Pharmacokinetic studies reveal that these derivatives exhibit an acceptable predictive ADMET profile (Absorption, Distribution, Metabolism, Excretion and Toxicity) and good drug-likeness.

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“…There are only a few quinoxaline aryl ethers reported in the literature as anticancer agents (Abbas et al, 2015;Corona et al, 2009;Hazeldine et al, 2005;Tang et al, 2020;Xia et al, 2016), and there are no reports with quinoxine aryl ethers with anilides embedded as on date. Hence, in continuation to our ongoing research on anticancer activity (Chitti et al, 2021(Chitti et al, , 2022, and owing to the importance and novelty of these derivatives, we explored the anticancer potential of the quinoxaline aryl ether containing anilides.…”

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confidence: 99%

Design, synthesis, and biological evaluation of novel quinoxaline aryl ethers as anticancer agents

Nakka,

Raza,

Chaitanya

et al. 2024

Chem Biol Drug Des

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We designed and synthesized thirty novel quinoxaline aryl ethers as anticancer agents, and the structures of final compounds were confirmed with various analytical techniques like Mass, 1H NMR, 13C NMR, FTIR, and elemental analyses. The compounds were tested against three cancer cell lines: colon cancer (HCT‐116), breast cancer (MDA‐MB‐231), prostate cancer (DU‐145), and one normal cell line: human embryonic kidney cell line (HEK‐293). The obtained results indicate that two compounds, FQ and MQ, with IC50 values < 16 μM, were the most active compounds. Molecular docking studies revealed the binding of FQ and MQ molecules in the active site of the c‐Met kinase (PDB ID: 3F66, 1.40 Å). Furthermore, QikProp ADME prediction and the MDS analysis preserved those critical docking data of both compounds, FQ and MQ. Western blotting was used to confirm the impact of the compounds FQ and MQ on the inhibition of the c‐Met kinase receptor. The apoptosis assays were performed to investigate the mechanism of cell death for the most active compounds, FQ and MQ. The Annexin V/7‐AAD assay indicated apoptosis in MDA‐MB‐231 cells treated with FQ and MQ, with FQ (21.4%) showing a higher efficacy in killing MDA‐MB‐231 cells than MQ (14.25%). The Caspase 3/7 7‐AAD assay further supported these findings, revealing higher percentages of apoptotic cells for FQ‐treated MDA‐MB‐231 cells (41.8%). The results obtained from the apoptosis assay conclude that FQ exhibits better anticancer activity against MDA‐MB‐231 cells than MQ.

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Design, synthesis and biological evaluation of 7–(5–((substituted – amino)-methyl)-thiophen–2–yl)-spiro-[chroman–2,4′–piperidin]–4–one hydrochloride analogues as anticancer agents

Cited by 10 publications

References 28 publications

New Potential Agents for Malignant Melanoma Treatment—Most Recent Studies 2020–2022

New Potential Agents for Malignant Melanoma Treatment—Most Recent Studies 2020–2022

Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds

Design, synthesis, and biological evaluation of novel quinoxaline aryl ethers as anticancer agents

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