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Ukr. Bioorg. Acta 2020, Vol. 15, N2最新文献

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Synthesis and evaluation of new thiazole-containing rhodanine-3-alkanoic acids as inhibitors of protein tyrosine phosphatases and glutathione S-transferases 新型含噻唑罗丹宁-3-烷酸作为蛋白酪氨酸磷酸酶和谷胱甘肽s -转移酶抑制剂的合成与评价
Ukr. Bioorg. Acta 2020, Vol. 15, N2 Pub Date : 2020-12-30 DOI: 10.15407/bioorganica2020.02.033
O. Kobzar, V. Sinenko, Yu. V. Shulha, Vlasyslav Buldenko, D. Hodyna, S. Pilyo, V. Brovarets, A. Vovk
{"title":"Synthesis and evaluation of new thiazole-containing rhodanine-3-alkanoic acids as inhibitors of protein tyrosine phosphatases and glutathione S-transferases","authors":"O. Kobzar, V. Sinenko, Yu. V. Shulha, Vlasyslav Buldenko, D. Hodyna, S. Pilyo, V. Brovarets, A. Vovk","doi":"10.15407/bioorganica2020.02.033","DOIUrl":"https://doi.org/10.15407/bioorganica2020.02.033","url":null,"abstract":"Thiazole-containing derivatives of rhodanine-3-alkanoic acids with propanoic or undecanoic acid groups were synthesized and evaluated as inhibitors of some protein tyrosine phosphatases and glutathione S-transferases. The rhodanines bearing longer carboxylated N-alkyl chain were found to inhibit PTP1B, MEG1, MEG2, and VE-PTP as well as GST from equine liver and GSTA1-1 with IC50 values in the low micromolar range. The inhibitory effect on protein tyrosine phosphatase activity depends on substituent at position 2 of the thiazole ring. The best compound showed a competitive type of VE-PTP inhibition. In case of GST from equine liver, the inhibition was of mixed or non-competitive type with respect to glutathione or CDNB substrate, respectively. Possible binding modes of the inhibitors were discussed based on molecular docking calculations.","PeriodicalId":23445,"journal":{"name":"Ukr. Bioorg. Acta 2020, Vol. 15, N2","volume":"216 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86624983","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Some pharmacological properties of 4-[3-(5-bromo-2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5H-thiazol-2-one 4-[3-(5-溴-2-羟基苯基)-5-苯基-3,4-二氢吡唑-2-基]- 5h -噻唑-2-酮的一些药理性质
Ukr. Bioorg. Acta 2020, Vol. 15, N2 Pub Date : 2020-12-30 DOI: 10.15407/bioorganica2020.02.041
A. Kryshchyshyn-Dylevych
{"title":"Some pharmacological properties of 4-[3-(5-bromo-2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5H-thiazol-2-one","authors":"A. Kryshchyshyn-Dylevych","doi":"10.15407/bioorganica2020.02.041","DOIUrl":"https://doi.org/10.15407/bioorganica2020.02.041","url":null,"abstract":"A series of 3,5-diaryl pyrazolyl thiazolinones were designed and synthesized as potential biologically active compounds. The study of anticancer activity of 4-[3-(5-bromo-2-hydroxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]-5H-thiazol-2-one (1) revealed its high antiproliferative activity against a panel of cancer cells with the lowest growth inhibition concentration (GI50) towards leukemic cell line SR (0.0351 µМ) and ovarian cancer cell line OVCAR-3 (0.248 µМ). It was also found that pyrazolyl thiazolinone 1 inhibited growth of Trypanosoma brucei brucei by 98,8% at a concentration of 10 µg/mL. The in-depth cytotoxicity study of compound 1 on human hepatocellular carcinoma HepG2 cells and non-tumorigenic murine fibroblast Balb/c 3T3 in MTT, NRU, TPC and LDH assays showed that normal cells were less sensitive to compound 1 than the cancer cells; its action had led to a disintegration of the cell membrane, inhibition of mitochondrial and lysosomal activity, and proliferation of cancer cells. The highest selectivity were detected in the LDH assay.","PeriodicalId":23445,"journal":{"name":"Ukr. Bioorg. Acta 2020, Vol. 15, N2","volume":"57 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80442717","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Features of the synthesis and biological evaluation of 3-(carboxyphenyl)chromones 3-(羧基苯基)色酮的合成特点及生物学评价
Ukr. Bioorg. Acta 2020, Vol. 15, N2 Pub Date : 2020-12-30 DOI: 10.15407/bioorganica2020.02.00
O. Shablykina, V. Moskvina, V. Khilya
{"title":"Features of the synthesis and biological evaluation of 3-(carboxyphenyl)chromones","authors":"O. Shablykina, V. Moskvina, V. Khilya","doi":"10.15407/bioorganica2020.02.00","DOIUrl":"https://doi.org/10.15407/bioorganica2020.02.00","url":null,"abstract":"Flavonoids and their derivatives have historically been a source of therapeutic agents. Every year, more and more data is published on new flavonoid compounds, both synthetic and isolated from natural sources, and their innumerable physiological and pharmacological activities. This review presents synthetic routes towards 3-(carboxyphenyl)chromones and evaluation of their biological activity as published in both journal and patent literature. We have focused specifically on the 3-(carboxyphenyl)chromones, because while methods of synthesis and biological activity of 2(3)-substituted and 2,3-disubstituted chromones are well studied, literature data on isoflavones containing a carboxyl, ester, or amide group in ring B is scarce and fragmentary. The presented generalization of synthetic strategies and biological activity of 3-(carboxyphenyl)chromone derivatives demonstrates that this class of compounds can be targeted for discovery of new drugs and can be readily prepared owing to recent advances in synthetic organic and medicinal chemistry.","PeriodicalId":23445,"journal":{"name":"Ukr. Bioorg. Acta 2020, Vol. 15, N2","volume":"93 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83836722","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Amino acid sulfonamides based on 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride 以4-(1-氧- 1h -异色胺-3-基)苯磺酰氯为基的氨基酸磺酰胺类化合物
Ukr. Bioorg. Acta 2020, Vol. 15, N2 Pub Date : 2020-12-30 DOI: 10.15407/bioorganica2020.02.027
Anastasiia Riabchenko, O. Shablykina, S. Shilin, S. Chumachenko, V. Khilya
{"title":"Amino acid sulfonamides based on 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride","authors":"Anastasiia Riabchenko, O. Shablykina, S. Shilin, S. Chumachenko, V. Khilya","doi":"10.15407/bioorganica2020.02.027","DOIUrl":"https://doi.org/10.15407/bioorganica2020.02.027","url":null,"abstract":"The creation of new amino acid derivatives of 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride 1 was investigated. The interaction of the sulfonyl chloride 1 with amino acid methyl esters (hydrochlorides) in 1,4-dioxane in the presence of triethylamine led to the corresponding amino acid sulfonamide derivatives of isocoumarin. The reaction of the sulfonyl chloride 1 with phenylalanine in the basic aqueous solution was complicated by the lactone system disclosure and led to 2'-carboxydeoxybenzoin ultimately (namely, 2-(2-(4-(N-(1-carboxy-2-phenylethyl)sulfamoyl)phenyl)-2-oxoethyl)benzoic acid). Similar product was obtained by the alkali hydrolysis of methyl ((4-(1-oxo-1H-isochromen-3-yl)phenyl)sulfonyl)leucinate.","PeriodicalId":23445,"journal":{"name":"Ukr. Bioorg. Acta 2020, Vol. 15, N2","volume":"14 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82651988","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Synthesis and anticancer activity of 5-sulfonyl derivatives of 1,3-oxazole-4-carboxylates 1,3-恶唑-4-羧酸酯5-磺酰基衍生物的合成及其抗癌活性
Ukr. Bioorg. Acta 2020, Vol. 15, N2 Pub Date : 2020-12-30 DOI: 10.15407/bioorganica2020.02.013
S. Pilyo, Оlexandr Kozachenko, V. Zhirnov, M. Kachaeva, O. Kobzar, A. Vovk, V. Brovarets
{"title":"Synthesis and anticancer activity of 5-sulfonyl derivatives of 1,3-oxazole-4-carboxylates","authors":"S. Pilyo, Оlexandr Kozachenko, V. Zhirnov, M. Kachaeva, O. Kobzar, A. Vovk, V. Brovarets","doi":"10.15407/bioorganica2020.02.013","DOIUrl":"https://doi.org/10.15407/bioorganica2020.02.013","url":null,"abstract":"A series of new 2-aryl 5-sulfonyl-1,3-oxazole-4-carboxylates for NCI anticancer screening protocol against 60 cancer cell lines were synthesized. Screening was performed in vitro on 60 cell lines of lungs, kidneys, CNS, ovaries, prostate, and breast cancer, leukemia, and melanoma. Methyl 5-benzylsulfonyl-2-phenyl-1,3-oxazole-4-carboxylate 15 exhibited potent and broad range of cytotoxic activity against tested human cancer cells with average GI50, TGI, and LC50 values of 5.37·10-6, 1.29·10-5 and 3.6·10-5 mol/L respectively. Molecular docking was used to evaluate the possible interaction of compound 15 with tubulin as well as a complex formation with CDK2.","PeriodicalId":23445,"journal":{"name":"Ukr. Bioorg. Acta 2020, Vol. 15, N2","volume":"20 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82574439","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 2
In silico study of binding affinity of nitrogenous bicyclic heterocycles: fragment-to-fragment approach 含氮双环杂环结合亲和力的硅晶研究:片段对片段的方法
Ukr. Bioorg. Acta 2020, Vol. 15, N2 Pub Date : 2020-12-30 DOI: 10.15407/bioorganica2020.02.049
Yevheniia Velihina, N. Obernikhina, S. Pilyo, M. Kachaeva, O. Kachkovsky, V. Brovarets
{"title":"In silico study of binding affinity of nitrogenous bicyclic heterocycles: fragment-to-fragment approach","authors":"Yevheniia Velihina, N. Obernikhina, S. Pilyo, M. Kachaeva, O. Kachkovsky, V. Brovarets","doi":"10.15407/bioorganica2020.02.049","DOIUrl":"https://doi.org/10.15407/bioorganica2020.02.049","url":null,"abstract":"The binding affinity of model aromatic amino acids and heterocycles and their derivatives condensed with pyridine were investigated in silico and are presented in the framework of fragment-to-fragment approach. The presented model describes interaction between pharmacophores and biomolecules. Scrupulous data analysis shows that expansion of the π-electron system by heterocycles annelation causes the shifting up of high energy levels, while the appearance of new the dicoordinated nitrogen atom is accompanied by decreasing of the donor-acceptor properties. Density Functional Theory (DFT) wB97XD/6-31(d,p)/calculations of π-complexes of the heterocycles 1-3 with model fragments of aromatic amino acids, which were formed by π-stack interaction, show an increase in the stabilization energy of π-complexes during the moving from phenylalanine to tryptophan. DFT calculation of pharmacophore complexes with model proton-donor amino acid by the hydrogen bonding mechanism (H-B complex) shows that stabilization energy (DE) increases from monoheterocycles to their condensed derivatives. The expansion of the π-electron system by introducing phenyl radicals to the oxazole cycle as reported earlier [18] leads to a decrease in the stabilization energy of the [Pharm-BioM] complexes in comparison with the annelated oxazole by the pyridine cycle.","PeriodicalId":23445,"journal":{"name":"Ukr. Bioorg. Acta 2020, Vol. 15, N2","volume":"50 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86111166","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Condition-based switching the multicomponent reactions of 5-amino-3-(methylthio)-1,2,4-triazole, aromatic aldehydes, and pyruvic acid 基于条件开关的5-氨基-3-(甲基硫)-1,2,4-三唑、芳香醛和丙酮酸的多组分反应
Ukr. Bioorg. Acta 2020, Vol. 15, N2 Pub Date : 2020-12-30 DOI: 10.15407/bioorganica2020.02.022
Yana I Sakhno, Maksym Mykhailenko, M. Kolosov, Elena H. Shvets, V. Musatov, N. Chorna, S. Desenko, V. Chebanov
{"title":"Condition-based switching the multicomponent reactions of 5-amino-3-(methylthio)-1,2,4-triazole, aromatic aldehydes, and pyruvic acid","authors":"Yana I Sakhno, Maksym Mykhailenko, M. Kolosov, Elena H. Shvets, V. Musatov, N. Chorna, S. Desenko, V. Chebanov","doi":"10.15407/bioorganica2020.02.022","DOIUrl":"https://doi.org/10.15407/bioorganica2020.02.022","url":null,"abstract":"The multicomponent reactions of 5-amino-3-methylthio-1,2,4-triazole with aromatic aldehydes and pyruvic acid were studied using conventional thermal heating and ultrasonic activation at room temperature. Under conventional heating, dihydrotriazolopyrimidine derivatives were formed in both two- and three-component treatments. In the case of ultrasonic activation, the multicomponent reaction led to the formation of 7-hydroxytetrahydrotriazolopyrimidines.","PeriodicalId":23445,"journal":{"name":"Ukr. Bioorg. Acta 2020, Vol. 15, N2","volume":"3 2-3","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91474419","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 2
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