Synthesis and X-ray study of dispiro 8-nitroquinolone analogues and their cytotoxic properties against human cervical cancer HeLa cells

Shyamsivappan, Selvaraj; Vivek, Raju; Saravanan, Arjunan; Arasakumar, Thangaraj; Gopalan, Subashini; Suresh, T. M.; Shankar, Ravi; Mohan, P. S.

doi:10.1039/c8md00482j

Cited by 26 publications

(18 citation statements)

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“…Recently we have reported new thiosemicarbazones, spiro pyrrolo oxindoles, indenoquinoxalines, and pyran derivatives from 8-nitroquinolones that exhibited potential activity towards cervical and breast cancer cells. 26–29 Hence, we selected specified cancer cell lines HeLa and MCF-7 to evaluate the cytotoxicity properties of the thiadiazoline spiro quinoline derivatives 4a–l . The toxicity of the compounds was evaluated by using MCF10A non-tumorigenic epithelial breast cells.…”

Section: Resultsmentioning

confidence: 99%

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New N-(3′-acetyl-8-nitro-2,3-dihydro-1H,3′H-spiro[quinoline-4,2′-[1,3,4]thiadiazol]-5′-yl) acetamides induced cell death in MCF-7 cells via G2/M phase cell cycle arrest

et al. 2022

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Section: Resultsmentioning

confidence: 99%

“…25 Because of these crucial activities of quinoline scaffolds, recently we have reported 8-nitroquinolone based compounds, which displayed good antitumor properties. 26–29…”

Section: Introductionmentioning

confidence: 99%

New N-(3′-acetyl-8-nitro-2,3-dihydro-1H,3′H-spiro[quinoline-4,2′-[1,3,4]thiadiazol]-5′-yl) acetamides induced cell death in MCF-7 cells via G2/M phase cell cycle arrest

et al. 2022

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“…Recently we have reported a new thiosemicarbazones, spiro pyrrolo oxindoles, indenoquinoxalines and pyarn derivatives from 8nitroquinolones that exhibited potential activity towards the cervical and breast cancer cells. [26][27][28][29] Hence, we selected speci ed cancer cell lines HeLa and MCF-7 to evaluate the cytotoxicity properties of the thiadiazoline spiro quinoline derivatives 4a-l. The toxicity of the compounds was evaluated by using MCF10A non-tumorigenic epithelial breast cells.…”

Section: Plausible Reaction Mechanism For Formation Of Desired Compoundsmentioning

confidence: 99%

“…Because of these crucial activities of quinoline scaffolds, recently we have reported 8-nitroquinolone based compounds, that resulting good antitumor properties. [26][27][28][29] Prompted by the early reports of the thiadiazole and quinoline motifs, herein, we synthesized a novel thiadiazoline spiro quinoline from 8-nitro quinoline thiosemicarbazones. All the synthesized thiadiazoline spiro quinoline compounds were assessed in vitro anticancer properties against HeLa and MCF-7 cells.…”

Section: Introductionmentioning

confidence: 99%

Novel Thiadiazoline Spiro Quinoline Analogues Induced Cell death in MCF-7 cells via G2/M Phase Cell Cycle Arrest

Shyamsivappan

Vivek

Suresh

et al. 2021

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A progression of novel thiadiazoline spiro quinoline derivatives were synthesized from potent thiadiazoline spiro quinoline derivatives . The synthesized compounds portrayed by different spectroscopic studies and single X-ray crystallographic studies. The compounds were assessed for in vitro anticancer properties towards MCF-7 and HeLa cells. The compounds showed superior inhibition action MCF-7 malignant growth cells. Amongst, the compound 4a showed significant inhibition activity, the cell death mechanism was evaluated by fluorescent staining, and flow cytometry, RT-PCR, and western blot analyses. The in vitro anticancer results revealed that the compound 4a induced apoptosis by inhibition of estrogen receptor alpha (ERα) and G2/M phase cell cycle arrest. The binding affinity of the compounds with ERα and pharmacokinetic properties were confirmed by molecular docking studies.

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“…The large library of the spirooxindole scaffold was generated with diverse pharmaceutical activities including low toxicity, acceptable bioavailability, and high efficiency [ 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 ]. In this paper, we describe in detail the synthesis of the spirooxindole analogs with significant bioactivities against the cancer cell in vitro.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Synthesis of the Di-Spirooxindole Analogs Based Oxindole and Cyclohexanone Moieties as Potential Anticancer Agents

et al. 2021

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A new series of di-spirooxindole analogs, engrafted with oxindole and cyclohexanone moieties, were synthesized. Initially, azomethine ylides were generated via reaction of the substituted isatins 3a–f (isatin, 3a, 6-chloroisatin, 3b, 5-fluoroisatin, 3c, 5-nitroisatin, 3d, 5-methoxyisatin, 3e, and 5-methylisatin, 3f, and (2S)-octahydro-1H-indole-2-carboxylic acid 2, in situ azomethine ylides reacted with the cyclohexanone based-chalcone 1a–f to afford the target di-spirooxindole compounds 4a–n. This one-pot method provided diverse structurally complex molecules, with biologically relevant spirocycles in a good yields. All synthesized di-spirooxindole analogs, engrafted with oxindole and cyclohexanone moieties, were evaluated for their anticancer activity against four cancer cell lines, including prostate PC3, cervical HeLa, and breast (MCF-7, and MDA-MB231) cancer cell lines. The cytotoxicity of these di-spirooxindole analogs was also examined against human fibroblast BJ cell lines, and they appeared to be non-cytotoxic. Compound 4b was identified as the most active member of this series against prostate cancer cell line PC3 (IC50 = 3.7 ± 1.0 µM). The cyclohexanone engrafted di-spirooxindole analogs 4a and 4l (IC50 = 7.1 ± 0.2, and 7.2 ± 0.5 µM, respectively) were active against HeLa cancer cells, whereas NO2 substituted isatin ring and meta-fluoro-substituted (2E,6E)-2,6-dibenzylidenecyclohexanone containing 4i (IC50 = 7.63 ± 0.08 µM) appeared to be a promising agent against the triple negative breast cancer MDA-MB231 cell line. To explore the plausible mechanism of anticancer activity of di-spirooxindole analogs, molecular docking studies were investigated which suggested that spirooxindole analogs potentially inhibit the activity of MDM2.

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Synthesis and X-ray study of dispiro 8-nitroquinolone analogues and their cytotoxic properties against human cervical cancer HeLa cells

Abstract: A series of unique dispiro 8-nitroquinolone analogues has been obtained through a one pot three-component reaction.

Cited by 26 publications

References 45 publications

New N-(3′-acetyl-8-nitro-2,3-dihydro-1H,3′H-spiro[quinoline-4,2′-[1,3,4]thiadiazol]-5′-yl) acetamides induced cell death in MCF-7 cells via G2/M phase cell cycle arrest

New N-(3′-acetyl-8-nitro-2,3-dihydro-1H,3′H-spiro[quinoline-4,2′-[1,3,4]thiadiazol]-5′-yl) acetamides induced cell death in MCF-7 cells via G2/M phase cell cycle arrest

Novel Thiadiazoline Spiro Quinoline Analogues Induced Cell death in MCF-7 cells via G2/M Phase Cell Cycle Arrest

Stereoselective Synthesis of the Di-Spirooxindole Analogs Based Oxindole and Cyclohexanone Moieties as Potential Anticancer Agents

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