One‐Pot Synthesis of New (1,3‐Thiazolo[5,4‐<i>b</i>]pyridin‐2‐yl)benzenediols and Their Antiproliferative Activities against Human Cancer Cell Lines

Matysiak, Joanna; Karpińska, Monika; Niewiadomy, Andrzej; Wietrzyk, Joanna; Kłopotowska, Dagmara

doi:10.1002/cbdv.201100007

Cited by 6 publications

(2 citation statements)

References 31 publications

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“…Structure–activity elucidation exhibited that the presence of a chlorine atom or alkyl substituent (methyl or ethyl) in position 5 of the resorcinol ring has a beneficial effect on the potency of compounds. A similar spectrum of biological activity and analogous effects of resorcinol modification on activity were found for 1,3-thiazolo[5,4- b ]pyridines [ 33 ] and 1 H -benzimidazoles [ 34 ].…”

Section: Introductionsupporting

confidence: 53%

Synthesis, characterization, and pharmacological evaluation of novel azolo- and azinothiazinones containing 2,4-dihydroxyphenyl substituent as anticancer agents

et al. 2015

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We reported the synthesis and characterization of a series of azolo- and azino[1,3]thiazinones containing the 2,4-dihydroxyphenyl substituent. The compounds were prepared by a new one-step reaction of aryl-modified sulfinylbis[(2,4-dihydroxyphenyl)methanethione]s and the corresponding aminoazolo(azino)carboxamides. Their chemical structures were confirmed by IR, NMR: 1H, 13C, HSQC, and EI-MS spectral data. The compounds inhibited proliferation and viability of lung cancer A549, colon cancer HT-29, and glioma C6 cells in a structure- and concentration-dependent manner. The activity of some analogues was below 10 μmol dm−3 (IC50). Glioma C6 cells were the most sensitive to tested compounds. Generally, the derivatives were not toxic for the skin fibroblast HSF culture. Moreover, some of them exerted a protective effect on the treated normal cells. Evaluation of compound properties in silico showed that they possess significant drug-like characteristics and most of them display a low toxicity.Graphical abstract

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Section: Introductionsupporting

confidence: 53%

Synthesis, characterization, and pharmacological evaluation of novel azolo- and azinothiazinones containing 2,4-dihydroxyphenyl substituent as anticancer agents

et al. 2015

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“…However, the information on antitumor activity of the mentioned bicycle derivatives of 4-thiazolidones is still missing. Up to now just a few compounds of such chemical structure have been tested against some human tumor cell lines in vitro [1,12]. Several studies point out that 4-thiazolidone based bicyclic analogues, in particular pyrazole and isoxazole derivatives, can act as inhibitors of HSP90, an ATP-dependent molecular chaperon [12].…”

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confidence: 99%

Synthesis and evaluation of antitumor activity ofsome thiazolo[4,5-b]pyridines

et al. 2012

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Aim. To synthesize a series of novel 3H-thiazolo[4,5-b]pyridine-2-ones by structural modification of the core heterocycle in its N3- and N6-positions and to evaluate their anticancer activity in vitro on several tumor cell lines. Methods. Organic synthesis, 1H-NMR spectroscopy, trypan blue cell viability assay. Results. A new convenient synthetic approach was developed and optimized conditions were studied for the reaction of preparation of 3H- thiazolo[4,5-b]pyridin-2-one derivatives. 5,7-Dimethyl-3H-thiazolo[4,5-b]pyridin-2-one and 6-phenylazo-5,7- dimethyl-3H-thiazolo[4,5-b]pyridin-2-one were obtained by [3 + 3]cyclocondensation of 4-iminothiazolidone- 2 with acetylacetone and phenylazoacetylacetone in methanol medium in the presence of sodium methylate. They were used as starting compounds for further structural modification of the core thiazolo[4,5-b]pyridine heterocycle in its 3- and 6-positions. On the basis of in vitro cytotoxicity studies of synthesized compounds several structure-functional relationships underlying anticancer potential of 5,7-dimethyl-3H-thiazolo[4,5-b]pyridin- 2-one derivatives were identified. Conclusions. 3H-thiazolo[4,5-b]pyridin-2-one can be considered as a promising molecular scaffold for rational design of potential anticancer drug candidates. Introduction of phenylazo substitute at C6-position of 3H-thiazolo[4,5-b]pyridin-2-one proved to be the most efficient, as it led to 3-fold increase of its anticancer potential

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Synthesis of 2-(2,4-dihydroxyphenyl)thieno-1,3-thiazin-4-ones, their lipophilicity and anticancer activity in vitro

et al. 2015

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A new one-step synthesis of novel biologically active 2-substituted 2,4-dihydroxyphenyl-4[Formula: see text]-thieno[3,2-[Formula: see text]][1,3]thiazin-4-ones and 4[Formula: see text]-thieno[2,3-[Formula: see text]][1,3]thiazin-4-ones has been elaborated and described. The compounds were prepared by the reaction of aryl-modified sulfinylbis [(2,4-dihydroxyphenyl)methanethione]s and the corresponding aminothiophenecarboxamides. The derivatives showed anticancer activity in vitro. These compounds inhibited the proliferation and viability of lung cancer A549, colon cancer HT-29 and glioma C6 cells in a concentration-dependent manner. Some of the derivatives had no influence on normal skin fibroblasts culture viability. Moreover, one compound (1b) showed the ability to inhibit DNA synthesis in cancer cells, especially in C6 cells, and was not toxic for normal oligodendrocytes and hepatocytes. Using reversed phase RP 18 HPLC and immobilised artificial membrane (IAM) chromatography the phase affinity of the compounds was determined. The influence of lipophilicity on the activity of compounds has been discussed.

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One‐Pot Synthesis of New (1,3‐Thiazolo[5,4‐b]pyridin‐2‐yl)benzenediols and Their Antiproliferative Activities against Human Cancer Cell Lines

Cited by 6 publications

References 31 publications

Synthesis, characterization, and pharmacological evaluation of novel azolo- and azinothiazinones containing 2,4-dihydroxyphenyl substituent as anticancer agents

Synthesis, characterization, and pharmacological evaluation of novel azolo- and azinothiazinones containing 2,4-dihydroxyphenyl substituent as anticancer agents

Synthesis and evaluation of antitumor activity ofsome thiazolo[4,5-b]pyridines

Synthesis of 2-(2,4-dihydroxyphenyl)thieno-1,3-thiazin-4-ones, their lipophilicity and anticancer activity in vitro

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