Pyrrole derivatives as potential anti-cancer therapeutics: synthesis, mechanisms of action, safety

Kuznietsova, Halyna; Dziubenko, Natalia; Byelinska, І.V.; Hurmach, Vasyl V.; Bychko, A.; Lynchak, Oksana; Milokhov, Demyd S.; Khilya, O. V.; Rybal’chenko, V. K.

doi:10.1080/1061186x.2019.1703189

Cited by 25 publications

(20 citation statements)

References 89 publications

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“…Spectroscopic data agree with those published [30]. (15). Acetonitrile (24 mL) was added to a mixture of 14 (1.64 mmol), pyrrole (8.2 mmol), potassium iodide (1.97 mmol), copper powder (1.64 mmol), and cesium carbonate (3.28 mmol).…”

Section: Synthesis Of 2-bromo-4-isopropyl-1-nitrobenzene (14)supporting

confidence: 82%

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Green Synthesis of New Pyrrolo [1,2-a] quinoxalines as Antiproliferative Agents in GPER-expressing Breast Cancer Cells

Carullo

Giordano

Aiello

2021

Journal of Chemistry

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4,5-Dihydropyrrolo [1,2-a]quinoxalines are interesting druggable scaffolds, with multifaceted biological properties, including anticancer properties targeting the G protein-coupled estrogen receptor 1 (GPER). In this work, the synthesis and preliminary antiproliferative activity of a small set of new 4,5-dihydropyrrolo[1,2-a]quinoxalines (18-20) and pyrrolo[1,2-a]quinoxalines (21, 22) has been reported, inspired by known antiproliferative agents (G-1, G-15, and G-36). The synthesis of the pyrroloquinoxalinic core was employed following the Pictet–Spengler reaction, using the surfactant p-dodecylbenzene sulphonic acid (p-DBSA), as catalyst. It demonstrated efficiency in the catalysis of the 4-phenylpyrrole [1,2-a] quinoxaline type compound formation in mild solvents such as water, ethanol, and hydroalcoholic solutions. In addition, the reactions proceeded in a short time (between 15 and 120 minutes) at room temperature and with high yields. The in vitro MTT assays showed that the presence of isopropyl groups furnished promising antiproliferative compounds. Although, the acetyl group provided also antiproliferative effects, breaking down its responsibility in the GPER transactivation. Nevertheless, it is possible to conclude that the 4,5-dihydropyrrolo[1,2-a]quinoxalines remain a feasible scaffold to develop anticancer agents against GPER-expressing cells.

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Section: Synthesis Of 2-bromo-4-isopropyl-1-nitrobenzene (14)supporting

confidence: 82%

“…Pyrrole derivatives are privileged structures in medicinal chemistry due to the uncountable pharmacological profiles [14]. Among the activities, the anticancer one has been described for different types of pyrrole derivatives [14,15].…”

Section: Introductionmentioning

confidence: 99%

Green Synthesis of New Pyrrolo [1,2-a] quinoxalines as Antiproliferative Agents in GPER-expressing Breast Cancer Cells

Carullo

Giordano

Aiello

2021

Journal of Chemistry

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“…These compounds induce apoptosis in colorectal cancer cells. Thus, these compounds could be used as inhibitors of EGFR and VEGFR, which may promote the realization of their pro-apoptotic and anti-cancer activities (Kuznietsova et al, 2020). In addition, another study found that pyrrole derivatives JG-03-14 showed reported anti-proliferative activity in MCF-7/caspase-3 cells and the MCF-7/ADR (multidrug-resistant) cell line.…”

Section: Discussionmentioning

confidence: 99%

PhTAD-Substituted Dihydropyrrole Compounds Regulate Apoptotic Cell Death in MCF-7 Cells

Yazgan

Mesci

Akşahin

et al. 2021

Erzincan Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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Breast cancer is the most common type of cancer amongst women. Apoptosis is known as a programmed cell death and this mechanism induces cancer cell death. Dihydropyrrole compounds contain a heterocyclic structure and these molecules have many biological effects including functioning as antioxidants and anticancer molecules. In this regard, the aim of this research was to investigate how PhTAD-substituted dihydropyrrole compounds affect the expression of apoptotic cell death proteins in the MCF-7 cells. The levels of Bax, Bcl-2, and cleaved caspase-3 proteins in the MCF-7 cells were measured using the ELISA method. The results revealed that CI, CII, CIII, CV, CVII, CVIII, CXI and CXII increased Bax, while CXIII and CXIV markedly decreased Bax. In addition, compounds CI, CII, CIII, CVII, CVIII, CXI and CXII upregulated Bcl2. Conversely, CIV, and CXIV downregulated Bcl2. Moreover, CIV and CXIV increased the Bax/Bcl2 ratio. However, CVIII and CXIII decreased Bax/Bcl2 ratio. In addition, CI, CIV, CIX and CXII treatment increased cleaved caspase-3 in MCF-7 cells compared to the negative control. These findings indicate that the PhTADsubstituted dihydropyrrole derivative molecules induced apoptotic proteins as a potential regulator of cancer cell death.

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“…So, VEGF and EGFR inhibitors constitute therapies that inhibit different signaling pathways to overcome tumor resistance caused by the inhibition of a single. Because of this, Kuznietsova et al [ 118 ] reported the synthesis of novel pyrrole analogs as protein kinases inhibitors. Their investigation suggested that two compounds, namely chloro-1-(4-chlorobenzyl)-4-((3-(trifluoromethyl)phenyl)amino)-1H-pyrrole-2,5-dione (36 a) and 5-amino-4-(1,3-benzothyazol-2-yn)-1-(3-methoxyphenyl)-1,2-dihydro-3H-pyrrole-3-one (36 b), are the competitive inhibitors of EGFR and VEGFR (Fig.…”

Section: Anticancer Agentsmentioning

confidence: 99%

Therapeutic potential of pyrrole and pyrrolidine analogs: an update

Basha¹,

Basavarajaiah²,

Shyamsunder³

2022

Mol Divers

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The chemistry of nitrogen-containing heterocyclic compound pyrrole and pyrrolidine has been a versatile field of study for a long time for its diverse biological and medicinal importance . Biomolecules such as chlorophyll, hemoglobin, myoglobin, and cytochrome are naturally occurring metal complexes of pyrrole. These metal complexes play a vital role in a living system like photosynthesis, oxygen carrier, as well storage, and redox cycling reactions. Apart from this, many medicinal drugs are derived from either pyrrole, pyrrolidine, or by its fused analogs. This review mainly focuses on the therapeutic potential of pyrrole, pyrrolidine, and its fused analogs, more specifically anticancer, anti-inflammatory, antiviral, and antituberculosis. Further, this review summarizes more recent reports on the pyrrole, pyrrolidine analogs, and their biological potential. Graphical Abstract

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Pyrrole derivatives as potential anti-cancer therapeutics: synthesis, mechanisms of action, safety

Cited by 25 publications

References 89 publications

Green Synthesis of New Pyrrolo [1,2-a] quinoxalines as Antiproliferative Agents in GPER-expressing Breast Cancer Cells

Green Synthesis of New Pyrrolo [1,2-a] quinoxalines as Antiproliferative Agents in GPER-expressing Breast Cancer Cells

PhTAD-Substituted Dihydropyrrole Compounds Regulate Apoptotic Cell Death in MCF-7 Cells

Therapeutic potential of pyrrole and pyrrolidine analogs: an update

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