Synthesis and aminomethylation of 7-hydroxy-5-methoxyisoflavones

Mrug, Galyna P.; Bondarenko, S. P.; Khilya, V. P.; Frasinyuk, M. S.

doi:10.1007/s10600-013-0570-8

Cited by 14 publications

(10 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The aminomethylation of chromones with electron-withdrawing substituent in position 3 is possible by applying corresponding aminals [ 48 ]. Thus, the reaction of chromones 2 – 5 with various aminals led to regiospecific formation of 8-aminomethylchromones 7a – 7m ( Scheme 2 ) which was confirmed by the disappearance in 1 H-NMR spectra of the upfield (for 6-alkyl substituted chromones 2 – 4 ) peak or presence of H-6 doublet at 6.84–6.98 ppm with 3 J 8.3–8.8 Hz.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Benzothiazole and Chromone Derivatives as Potential ATR Kinase Inhibitors and Anticancer Agents

et al. 2022

View full text Add to dashboard Cite

Despite extensive studies and the great variety of existing anticancer agents, cancer treatment remains an aggravating and challenging problem. Therefore, the development of novel anticancer drugs with a better therapeutic profile and fewer side effects to combat this persistent disease is still necessary. In this study, we report a novel series of benzothiazole and chromone derivatives that were synthesized and evaluated for their anticancer activity as an inhibitor of ATR kinase, a master regulator of the DDR pathway. The cell viability of a set of 25 compounds was performed using MTT assay in HCT116 and HeLa cell lines, involving 72 h incubation of the compounds at a final concentration of 10 µM. Cells incubated with compounds 2c, 7h and 7l were found to show viability ≤50%, and were taken forward for dose–response studies. Among the tested compounds, three of them (2c, 7h and 7l) showed higher potency, with compound 7l exhibiting the best IC50 values in both the cell lines. Compounds 2c and 7l were found to be equally cytotoxic towards both the cell lines, namely, HCT116 and HeLa, while compound 7h showed better cytotoxicity towards HeLa cell line. For these three compounds, an immunoblot assay was carried out in order to analyze the inhibition of phosphorylation of Chk1 at Ser 317 in HeLa and HCT116 cells. Compound 7h showed inhibition of pChk1 at Ser 317 in HeLa cells at a concentration of 3.995 µM. Further analysis for Chk1 and pChk1 expression was carried out in Hela cells by treatment against all the three compounds at a range of concentrations of 2, 5 and 10 µM, wherein compound 7h showed Chk1 inhibition at 2 and 5 µM, while pChk1 expression was observed for compound 7l at a concentration of 5 µM. To support the results, the binding interactions of the compounds with the ATR kinase domain was studied through molecular docking, wherein compounds 2c, 7h and 7l showed binding interactions similar to those of Torin2, a known mTOR/ATR inhibitor. Further studies on this set of molecules is in progress for their specificity towards the ATR pathway.

show abstract

Section: Resultsmentioning

confidence: 99%

“…Compounds 1a [ 43 ], 1b [ 45 ], 1c [ 44 ], 1e [ 46 ], 2a [ 43 ], 2b [ 45 ], 2c [ 44 ], 2e [ 46 ], 3c [ 44 ], 6a – 6d [ 47 ], 8 [ 48 ], and 9a,b [ 49 ] were synthesized by procedures reported earlier.…”

Section: Methodsmentioning

confidence: 99%

Benzothiazole and Chromone Derivatives as Potential ATR Kinase Inhibitors and Anticancer Agents

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Compounds isolated from C. tricuspidata roots can be divided into chromones (1-2), isoflavonoids (3)(4)(5)(6), flavonols (7)(8), flavanonols (9-10) and flavanones (11)(12)(13)(14)(15)(16)(17). Overall, flavanones showed stronger pancreatic lipase inhibition than other groups in our assay system (Table 1).…”

mentioning

confidence: 86%

“…As a result, the CH 2 Cl 2 and EtOAc-soluble fraction of C. tricuspidata significantly inhibited pancreatic lipase activity in our assay system. Further chromatographic separation of these fractions afforded seventeen compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17). 10 Compounds 1-16 were identified as 5,7-dihydroxychromone (1), 5-hydroxy-2,2-dimethyl-2H,6H-benzodipyran-6-one (2), genistein (3), biochanin A (4), 3 0 -O-methylorobol (5), wighteone (6), kaempferol (7), morin (8), aromadendrine (9), (2R,3R)-2,3-dihydro-3,5,6,7-tetrahydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (10), naringenin (11), 5,7,3 0 ,5 0 -tetrahydroxyflavanone (12), 8-prenylnaringenin (13), cudraflavanone D (14), cudraflavanone A (15), and 2 0 ,5,7-trihydroxy-4,5 0 -(2,2-dimethylchromeno)-8-(3-hydroxy-3-methylbuthyl)flavanone (16), (Fig.…”

mentioning

confidence: 99%

“…1) by the analysis of their spectroscopic data and comparison with literature values. [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] Compound 17 was obtained as light brown syrup and gave HREIMS at 445.1666 (calcd 445.1651), consistent with a molecular formula of C 27 H 25 O 6 . 27 The IR spectrum showed the presence of hydroxyl (3289 cm À1 ) and carbonyl (1647 cm À1 ) groups.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Benzylated and prenylated flavonoids from the root barks of Cudrania tricuspidata with pancreatic lipase inhibitory activity

Jo¹,

Kim²,

Liu³

et al. 2015

Bioorganic & Medicinal Chemistry Letters

View full text Add to dashboard Cite

Enantioselektive Totalsynthese von (−)‐Mehranin, (−)‐Methylenbismehranin und verwandten Aspidosperma‐Alkaloiden

2014

View full text Add to dashboard Cite

Wir berichten über eine effiziente und hochstereoselektive Strategie zur Synthese von Aspidosperma-Alkaloiden, die auf der transannularen Cyclisierung einer chiralen Lactamvorstufe basiert. Aufgrund der bevorzugten Konformation der Cyclisierungsvorstufe werden in diesem Schlüsselschritt drei neue Stereozentren des resultierenden, vielseitigen, pentacyclischen Intermediats mit exzellenter Diastereoselektivität aufgebaut. Eine anschließende stereoselektive Epoxidierung mit nachfolgender Formamidreduktion unter milden Bedingungen ermçglichte die erste Totalsynthese der Aspidosperma-Alkaloide (À)-Mehranin und (+)-(6S,7S)-Dihydroxy-N-methylaspidospermidin. Eine abschließende, Scandiumtrifluormethansulfonat-vermittelte Dimerisierung von (À)-Mehranin führte zur ersten Totalsynthese von (À)-Methylenbismehranin.Abbildung 1. Repräsentative monomere und dimere Aspidosperma-Alkaloide.

show abstract

Synthesis and aminomethylation of 7-hydroxy-5-methoxyisoflavones

Cited by 14 publications

References 21 publications

Benzothiazole and Chromone Derivatives as Potential ATR Kinase Inhibitors and Anticancer Agents

Benzothiazole and Chromone Derivatives as Potential ATR Kinase Inhibitors and Anticancer Agents

Benzylated and prenylated flavonoids from the root barks of Cudrania tricuspidata with pancreatic lipase inhibitory activity

Enantioselektive Totalsynthese von (−)‐Mehranin, (−)‐Methylenbismehranin und verwandten Aspidosperma‐Alkaloiden

Contact Info

Product

Resources

About