Interaction of 1-acylamino-2,2-dichloroethenyl(triphenyl)phosphonium chlorides with alkanolamines

Golovchenko, A. V.; Abdurakhmanova, E. R.; Vladimirov, S. O.; Brusnakov, Mykhailo Y.; Krupoder, T. O.; Sukhoveev, V. V.; Русанов, Эдуард Б.; Vydzhak, R. N.; Броварец, В. С.

doi:10.1080/10426507.2020.1759062

Cited by 2 publications

(3 citation statements)

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“…The synthesis of compounds 1 – 14 was accomplished by known approaches. [ 13 , 14 , 15 , 16 , 17 , 18 , 19 ] 5‐Amino‐1,3‐oxazol‐4‐yltriphenylphosphonium salts 1 – 7 were obtained starting from 2,2‐dichloroethenyl‐1‐acylaminotriphenylphosphonium chlorides ( Ia – c ) and aromatic or aliphatic amines (Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…[5‐[(2,3‐Dihydroxypropyl)amino]‐2‐phenyl‐1,3‐oxazol‐4‐yl]triphenylphosphonium perchlorate (3) was synthesized according to the method described in the article. [16] …”

Section: Methodsmentioning

confidence: 99%

“…was synthesized according to the method described in the article. [16] Yield: 69 %, 4. 4) was synthesized according to the method described in the article.…”

Section: [5-[(23-dihydroxypropyl)amino]-2-phenyl-13-oxazol-4-yl]triph...mentioning

confidence: 99%

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Evaluation of Anticancer Activity of 1,3‐Oxazol‐4‐ylphosphonium Salts in Vitro

et al. 2022

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A novel series of 1,3-oxazol-4-yltriphenylphosphonium salts has been synthesized and functionalized. Oxazole derivatives were subjected to NCI in vitro assessment. Seven most active derivatives have been selected for five-dose assay. Among them, compounds 9 and 4 ( [5-phenyl-2-[(4methylphenyl)amino]-1,3-oxazol-4-yl]triphenylphosphonium perchlorate) were the most active against all tested cancer subpanels. Statistical analysis of the total panel data showed average values of parameters of anticancer activity in the range of 0.3-1.1 μM (GI 50 ), 1.2-2.5 μM (TGI) and 5-6 μM (LC 50 ). It was found that the presence of phenyl or 4-methylphenyl groups at C(2) and C(5) in the oxazole ring is of critical importance for the manifestation of the anticancer activity. Matrix COMPARE analysis using LC 50 vector showed a high positive correlation of compound 9 with standard anticancer agents that can directly disrupt mitochondrial function, causing programmed death of cancer cells. The obtained results indicate the anticancer activity of 1,3-oxazol-4-ylphosphonium salts, which could be useful for developing new anticancer drugs. The most active of them can be recommended for further in-depth studies and synthesis of new derivatives with antitumor activity on their basis.

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Section: Resultsmentioning

confidence: 99%

“…[5‐[(2,3‐Dihydroxypropyl)amino]‐2‐phenyl‐1,3‐oxazol‐4‐yl]triphenylphosphonium perchlorate (3) was synthesized according to the method described in the article. [16] …”

Section: Methodsmentioning

confidence: 99%

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Evaluation of Anticancer Activity of 1,3‐Oxazol‐4‐ylphosphonium Salts in Vitro

et al. 2022

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New phosphorylated 5-(hydroxyalkylamino)-1,3-oxazoles as potential anticancer agents

Bahrieieva,

Golovchenko,

Golovchenko

et al. 2023

Ukr. Bioorg. Acta

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Eight new phosphorylated 5-(hydroxyalkylamino)-1,3-oxazoles were designed and tested for their ability to inhibit cancer cell growth. These compounds were evaluated against complete human tumor cell lines NCI-60. Only three compounds showed antitumor activity in the single dose assay, which were taken in the five dose assay. Compounds 7 and 8 showed the same average antiproliferative activity and cytotoxicity against sensitive cell lines of the general panel. However, compound 8 showed cytotoxicity to more lines than 7. By all parameters, these compounds were more active than compounds 5. Compounds 7 and 8 also showed high and similar antiproliferative activity in the concentration range GI50: 1-6 and TGI: 6-14 μM against all subpanels. Their cytotoxicity was in the concentration range of 25-54 μM. Compound 5 showed the same activity, with the exception of the leukemia, non-small cell lung cancer and ovarian cancer subpanels against which their activity was lower. When analyzing the structure-activity, it turned out that among the phosphorylated oxazole derivatives, only compounds containing the triphenylphosphonium cation (TPP+) in the 4th position of the oxazole ring exhibit antitumor activity. Moreover, the replacement of the phenyl radical in the 2nd position of the oxazole scaffold with a methyl radical led to the disappearance of the activity. The COMPARE algorithm reveals a high correlation of the antiproliferative activity of the tested compounds with the antitumor agents phyllantoside and chromomycin A3 in the GI50 vector and moderate with phyllantoside in the TGI vector. The target of all standard drugs that correlate with the cytotoxicity of the studied compounds, with the exception of didemnin, is DNA. Unlike standard compounds, synthesized active compounds carry a delocalized TPP+, which delivers them predominantly to mitochondria due to a much more hyperpolarized potential of the mitochondrial membrane in cancer cells than in normal ones. Therefore, their anticancer activity is most likely due to a disturbation of the structural and functional state of the latter due to interference with their intrinsic protein-synthesizing apparatus of mitochondria. The data obtained allow us to consider 5-(hydroxyalkylamino)-1,3-oxazoles loaded with TPP+ as leading compounds for further in-depth study and synthesis of new TPP+-containing 1,3-oxazole derivatives with antitumor activity

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Interaction of 1-acylamino-2,2-dichloroethenyl(triphenyl)phosphonium chlorides with alkanolamines

Cited by 2 publications

References 18 publications

Evaluation of Anticancer Activity of 1,3‐Oxazol‐4‐ylphosphonium Salts in Vitro

Evaluation of Anticancer Activity of 1,3‐Oxazol‐4‐ylphosphonium Salts in Vitro

New phosphorylated 5-(hydroxyalkylamino)-1,3-oxazoles as potential anticancer agents

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