Evaluation of angularly condensed diquinothiazines as potential anticancer agents

Jeleń, Małgorzata; Pluta, Krystian; Latocha, Małgorzata; Morak‐Młodawska, Beata; Suwińska, Kinga; Kuśmierz, Dariusz

doi:10.1016/j.bioorg.2019.04.005

Cited by 11 publications

(13 citation statements)

References 45 publications

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“…It was also found that the replacement of benzene ring with quinoline in the azaphenothiazine framework diminished the cytotoxic potential of the molecule. 266 Jeleń et al, 267 synthesized angularly fused diquinothiazines and gauged them for their anticancer activity against a few selected carcinoma cells. Amongst the synthesized derivatives, most of the analogs presented noteworthy cancer cell growth inhibition against the SNB- Morak-Młodawska et al, 269 in 2014 developed new diazaphenothiazines with substitution at its 10th position via an S-N type Smiles rearrangement reaction and further evaluated their biological activity.…”

Section: Phenothiazine and Azaphenothiazinementioning

confidence: 99%

“…Jeleń et al, 267 synthesized angularly fused diquinothiazines and gauged them for their anticancer activity against a few selected carcinoma cells. Amongst the synthesized derivatives, most of the analogs presented noteworthy cancer cell growth inhibition against the SNB‐19, Caco‐2, MDA‐MB‐231, and A549 cell lines with the IC 50 values less than 3 μM which was found to be more potent than the reference compound cisplatin.…”

Section: Introductionmentioning

confidence: 99%

“…Compound 236 (IC 50 : 0.3 µM) was found to exhibit excellent activity against SNB‐19 cell line whereas, 237 (IC 50 : 0.3 µM) displayed prominent cytotoxicity against A549 carcinoma cells. Compound 236 was able to express in H3, TP53, CDKN1A, BCL‐2, and BAX genes which caused inhibition of the cellular proliferation (H3) and activation of the mitochondrial events of apoptosis (BAX/BCL‐2) in two tumor cell lines (SNB‐19 and Caco‐2) 267 …”

Section: Introductionmentioning

confidence: 99%

“…Compound 236 (IC 50 : 0.3 µM) was found to exhibit excellent activity against SNB-19 cell line whereas, 237 (IC 50 : 0.3 µM) displayed prominent cytotoxicity against A549 carcinoma cells. Compound 236 was able to express in H3, TP53, CDKN1A, BCL-2, and BAX genes which caused inhibition of the cellular proliferation (H3) and activation of the mitochondrial events of apoptosis (BAX/BCL-2) in two tumor cell lines (SNB-19 and Caco-2) 267. Jonczyk et al,268 screened diversely substituted azaphenothiazine hybrids, from which 25 molecules were found to show potential inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE).…”

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confidence: 99%

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Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Laxmikeshav

Kumari

Shankaraiah

2021

Medicinal Research Reviews

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This review article proposes a comprehensive report of the design strategies engaged in the development of various sulfur-bearing cytotoxic agents. The outcomes of various studies depict that the sulfur heterocyclic framework is a fundamental structure in diverse synthetic analogs representing a myriad scope of therapeutic activities. A number of five-, six-and seven-membered sulfur-containing heterocyclic scaffolds, such as thiazoles, thiadiazoles, thiazolidinediones, thiophenes, thiopyrans, benzothiazoles, benzothiophenes, thienopyrimidines, simple and modified phenothiazines, and thiazepines have been discussed. The subsequent studies of the derivatives unveiled their cytotoxic effects through multiple mechanisms (viz. inhibition of tyrosine kinases, topoisomerase I and II, tubulin, COX, DNA synthesis, and PI3K/Akt and Raf/MEK/ERK signaling pathways), and several others. Thus, our concise illustration explains the design strategy and anticancer potential of these five-and six-membered sulfur-containing heterocyclic molecules along with a brief outline on seven-membered sulfur heterocycles. The thorough assessment of antiproliferative activities with the reference drug allows a proficient assessment of the structure-activity relationships (SARs) of the diversely synthesized molecules of the series.

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Section: Phenothiazine and Azaphenothiazinementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Laxmikeshav

Kumari

Shankaraiah

2021

Medicinal Research Reviews

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“…Neuroleptic phenothiazines became the foundation for numerous studies on modified phenothiazine systems that show a wide spectrum of biological activities, including: anticancer, antibacterial, antifungal, antiviral, and antiparasitic. This rich scientific material is the subject of numerous publications that can be found in the world literature every year [7,8,9,10,11,12,13,14,15,16].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Structural Characterization of Novel Diazaphenothiazines with 1,2,3-Triazole Substituents as Promising Antiproliferative Agents

et al. 2019

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A series of novel 1,2,3-triazole-diazphenothiazine hybrids was designed, synthesized, and evaluated for anticancer activity against four selected human tumor cell lines (SNB-19, Caco-2, A549, and MDA-MB231). The majority of the synthesized compounds exhibited significant potent activity against the investigated cell lines. Among them, compounds 1d and 4c showed excellent broad spectrum anticancer activity, with IC50 values ranging from 0.25 to 4.66 μM and 0.25 to 6.25 μM, respectively. The most promising compound 1d, possessing low cytotoxicity against normal human fibroblasts NHFF, was used for gene expression analysis using reverse transcription–quantitative real-time PCR (RT–qPCR). The expression of H3, TP53, CDKN1A, BCL-2, and BAX genes revealed that these compounds inhibited the proliferation in all cells (H3) and activated mitochondrial events of apoptosis (BAX/BCL-2).

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Synthesis of new pyrido[3,2-b][1,4]benzoxazines and -benzothiazines

et al. 2022

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Evaluation of angularly condensed diquinothiazines as potential anticancer agents

Cited by 11 publications

References 45 publications

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Design, Synthesis, and Structural Characterization of Novel Diazaphenothiazines with 1,2,3-Triazole Substituents as Promising Antiproliferative Agents

Synthesis of new pyrido[3,2-b][1,4]benzoxazines and -benzothiazines

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