Antiproliferative activity of thiazole and oxazole derivatives: A systematic review of in vitro and in vivo studies

Guerrero-Pepinosa, Nancy Y.; Cardona-Trujillo, María C.; Garzón-Castaño, Sandra Catalina; Veloza, Luz Ángela; Sepúlveda-Arias, Juan Carlos

doi:10.1016/j.biopha.2021.111495

Cited by 45 publications

(28 citation statements)

References 42 publications

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“…There is a vast number of thiazoles that exhibit a wide range of pharmacological activities, including antibacterial [ 29 ], anticancer [ 30 ], antifungal [ 31 ], anti-inflammatory [ 32 ], antioxidant [ 33 ] and anti-tubercular activities [ 34 ]. Therefore, we believe that the merging of pyrazole and thiazole moieties will result in a class of pharmacophores that exhibit promising biological activities; in fact, several previous works have reported their potential activities, such as anticonvulsant, anti-HIV, anti-inflammatory and anticancer activities [ 35 , 36 , 37 , 38 , 39 , 40 ].…”

Section: Introductionmentioning

confidence: 99%

Facile One-Pot Multicomponent Synthesis of Pyrazolo-Thiazole Substituted Pyridines with Potential Anti-Proliferative Activity: Synthesis, In Vitro and In Silico Studies

2021

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Pyrazolothiazole-substituted pyridine conjugates are an important class of heterocyclic compounds with an extensive variety of potential applications in the medicinal and pharmacological arenas. Therefore, herein, we describe an efficient and facile approach for the synthesis of novel pyrazolo-thiazolo-pyridine conjugate 4, via multicomponent condensation. The latter compound was utilized as a base for the synthesis of two series of 15 novel pyrazolothiazole-based pyridine conjugates (5–16). The newly synthesized compounds were fully characterized using several spectroscopic methods (IR, NMR and MS) and elemental analyses. The anti-proliferative impact of the new synthesized compounds 5–13 and 16 was in vitro appraised towards three human cancer cell lines: human cervix (HeLa), human lung (NCI-H460) and human prostate (PC-3). Our outcomes regarding the anti-proliferative activities disclosed that all the tested compounds exhibited cytotoxic potential towards all the tested cell lines with IC50 = 17.50–61.05 µM, especially the naphthyridine derivative 7, which exhibited the most cytotoxic potential towards the tested cell lines (IC50 = 14.62–17.50 µM) compared with the etoposide (IC50 = 13.34–17.15 µM). Moreover, an in silico docking simulation study was performed on the newly prepared compounds within topoisomerase II (3QX3), to suggest the binding mode of these compounds as anticancer candidates. The in silico docking results indicate that compound 7 was a promising lead anticancer compound which possesses high binding affinity toward topoisomerase II (3QX3) protein.

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Section: Introductionmentioning

confidence: 99%

Facile One-Pot Multicomponent Synthesis of Pyrazolo-Thiazole Substituted Pyridines with Potential Anti-Proliferative Activity: Synthesis, In Vitro and In Silico Studies

2021

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“…In essence, the aim of molecular hybridization is to produce a single chemical entity through combination of two or more distinct pharmacophore subunits present in the structures of two or more known bioactive derivatives. For example, pyrazole and thiazole derivatives can be cited as examples of the successful application of this strategy [2][3][4][5][6]. 5) is also based on 3-(pyrazol-3ylamino)-isoquinolin-1(2H)-ones [12].…”

Section: Introductionmentioning

confidence: 99%

“…The strong activity in suppressing proliferation and growth of glioblastoma cells [13], colorectal (SW620, HT29, GI50 = 23.8÷24.13 M) [14] and CNS (SF-295, GI = 55%) [15] human cancer cell lines was found for condensed derivatives having a 3-aminoisoquinolinone moiety (6). The unsaturated 5H-benzo [4,5]imidazo [1,2b]isoquinolin-1-one (7) exhibited significant Cdc25B inhibition (IC50 = 5.3 M) [11]. In this context, the consolidation of the 3aminoisoquinolinone template and novel carbo/heteroaromatic rings as novel pharmacophores seems to be promising for obtaining highly effective anticancer drugs.…”

Section: Introductionmentioning

confidence: 99%

Biological Evaluation of 3-Aminoisoquinolin-1(2H)-one Derivatives as Potential Anticancer Agents Authors Lyudmyla Potikha

2021

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Anticancer activity of a series of 3-(hetaryl/aryl)amino substituted isoquinolin-1(2H)-ones has been studied within the international scientific program “NCI-60 Human Tumor Cell Lines Screen”. Screening was performed in vitro on 60 cell lines of lungs, kidneys, CNS, ovaries, prostate, and breast cancer, epithelial cancer, leukemia, and melanoma. The most effective compounds were those with thiazolyl or pyrazolyl substituent at 3-amino group and had no substituents at C(4) of the isoquinoline cycle. We identified a new lead compound, 3-(1,3-thiazol-2-ylamino)isoquinolin-1(2H)-one 12, which effectively prevents tumor cell growth (average lg GI50 = -5.18, lg TGI = -4.1, lg LC50 > -4.0) with good selectivity.

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“…The literature survey on the synthesized five-membered heterocycles with two heteroatoms from 1,3-oxazoles class highlighted that they are also endowed with a wide range of potent pharmacological activities [ 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 ], such as antifungal, antibacterial (e.g., sulfaguanole with trade name: Enterocura, a sulfanilamide drug used for patients with acute diarrhea), anticancer (e.g., mubritinib), analgesic, antipyretic, anti-inflammatory (e.g., oxaprozin, a COX-2 inhibitor currently in the market, romazarit, the Roche candidate, which was withdrawn due to its toxicity profile), and anti-diabetic (e.g., darglitazone, an antihyperglycemic agent belonging to the glitazone class) effects. The structures of the representative bioactive synthetic compounds sharing the 1,3-oxazole scaffold are presented in Figure 2 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives

et al. 2021

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The multi-step synthesis, physico-chemical characterization, and biological activity of novel valine-derived compounds, i.e., N-acyl-α-amino acids, 1,3-oxazol-5(4H)-ones, N-acyl-α-amino ketones, and 1,3-oxazoles derivatives, bearing a 4-[(4-chlorophenyl)sulfonyl]phenyl moiety are reported here. The structures of the newly synthesized compounds were confirmed by spectral (UV-Vis, FT-IR, MS, 1H- and 13C-NMR) data and elemental analysis results, and their purity was determined by RP-HPLC. The new compounds were assessed for their antimicrobial activity and toxicity to aquatic crustacean Daphnia magna. Also, in silico studies regarding their potential mechanism of action and toxicity were performed. The antimicrobial evaluation revealed that the 2-{4-[(4-chlorophenyl)sulfonyl]benzamido}-3-methylbutanoic acid and the corresponding 1,3-oxazol-5(4H)-one exhibited antimicrobial activity against Gram-positive bacterial strains and the new 1,3-oxazole containing a phenyl group at 5-position against the C. albicans strain.

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Antiproliferative activity of thiazole and oxazole derivatives: A systematic review of in vitro and in vivo studies

Cited by 45 publications

References 42 publications

Facile One-Pot Multicomponent Synthesis of Pyrazolo-Thiazole Substituted Pyridines with Potential Anti-Proliferative Activity: Synthesis, In Vitro and In Silico Studies

Facile One-Pot Multicomponent Synthesis of Pyrazolo-Thiazole Substituted Pyridines with Potential Anti-Proliferative Activity: Synthesis, In Vitro and In Silico Studies

Biological Evaluation of 3-Aminoisoquinolin-1(2H)-one Derivatives as Potential Anticancer Agents Authors Lyudmyla Potikha

Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives

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