Synthesis and anticancer activity of novel halolactones with β-aryl substituents from simple aromatic aldehydes

Gładkowski, Witold; Skrobiszewski, Andrzej; Mazur, Marcelina; Siepka, Monika; Pawlak, Aleksandra; Obmińska-Mrukowicz, Bożena; Białońska, Agata; Poradowski, Dominik; Drynda, Angelika; Urbaniak, Mariusz

doi:10.1016/j.tet.2013.09.094

Cited by 47 publications

(60 citation statements)

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“…Comparing with the results obtained during the synthesis of iodolactones with phenyl (5a and 6a) and 4-methylphenyl ring (5b and 6b) 31 it could be presumed that this minor product is trans, cis γ -iodo-δ-lactone which in those cases constituted 24 and 22%, respectively. The clear predomination of products of 5-exo cyclization over the products of 6-endo cyclization as well as cis γ -lactones over their trans isomers were also observed in the course of iodolactonization of γ, δ-unsaturated acid with 4-methoxyphenyl ring.…”

Section: Synthesis Of Lactonesmentioning

confidence: 56%

“…Two major products were separated by column chromatography and their structures were established by comparative analysis of their spectral data with those obtained earlier for iodolactones 5a, b and 6a, b. 31 IR spectrum showed characteristic bands for γ -lactone ring at 1784 cm −1 for 5c and 1781 cm −1 for 6c. In the case of cis-δ-iodo-γ -lactone 5c, signal of H-5 proton was doublet of doublets (J = 10.8 and 5.4 Hz), whereas in case of trans-δ-iodo-γ -lactone 6c proton H-5 gave triplet (J = 5.4 Hz).…”

Section: Synthesis Of Lactonesmentioning

confidence: 94%

“…Among δ-iodo-γ -lactones compounds 5a, b and 6a, b were obtained earlier in a five-step synthesis from benzaldehyde and 4-methylbenzaldehyde. 31 Substrate in the synthesis of iodolactones 5c and 6c was (E)-4-(benzo[d] [1 ,3 ]-dioxol-5 -yl)-but-3-en-2-one (1), obtained earlier by Claisen-Schmidt condensation of piperonal with acetone under alkali conditions (NaOH). 30 Ketone 1 was reduced using NaBH 4 .…”

Section: Synthesis Of Lactonesmentioning

confidence: 99%

“…ias.ac.in/chemsci. Crystal data for lactone 5a were reported earlier by Gładkowski et al 31 and have been deposited with the Cambridge Crystallographic Data Centre (CCDC) as supplementary publication number 944820. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union road, Cambridge CB12 1EZ, UK (fax +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).…”

Section: Supplementary Informationmentioning

confidence: 99%

“…30 Iodolactones 5a, b and 6a, b were obtained earlier in five-step syntheses from benzaldehyde and 4-methylbenzaldehyde respectively. 31 Triethyl orthoacetate (purity 97%), tributyltin hydride (97%), dimethyl sulfoxide (DMSO, purity ≥ 99.9%) were purchased from Sigma-Aldrich (USA). Sodium borhydride (98%) was purchased from ABCR GmbH & Co. KG (Germany).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

et al. 2015

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Eighteen racemic β-aryl-γ -lactones derived from simple aromatic aldehydes have been obtained in the chemical synthesis. Iodolactones (5c and 6c) were synthesized from (E)-4-(benzo [d][1 ,3 ]-dioxol-5 -yl)-but-3-en-2-one (1). Reductive dehalogenation of iodolactones 5a-c and 6a-c afforded γ -ethyl-γ -lactones (7a-c, 8a-c) whereas the unsaturated lactones (9a-c, 10a-c) were obtained by dehydrohalogenation of iodolactones. All synthesized lactones were fully characterized by spectroscopic data (NMR, IR, HRMS) and subjected to the tests on the antifeedant activity towards Tribolium confusum, Trogoderma granarium and Sitophilus granaries as well to the tests on the antifungal activity towards four Fusarium species. The biological tests allowed to find some relationships between the structure and biological activity of the compounds studied. γ -Ethyl-γ -lactones 7a-c, 8a-c and unsaturated lactones 9a-c, 10a-c were usually stronger antifeedants than their parent iodolactones 5a-c and 6a-c. trans-Iodolactones 6a-c were more active than cis isomers 5a-c both in antifeedant and antifungal assays. The structure of aromatic substituent was the key factor in antifungal activity. The lactones with benzo [d][1,3]dioxole ring (5c, 6c, 7c, 8c, 9c) were the most active whereas those with unsubstituted benzene ring exhibited almost no activity.

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Section: Synthesis Of Lactonesmentioning

confidence: 56%

Section: Synthesis Of Lactonesmentioning

confidence: 94%

Section: Synthesis Of Lactonesmentioning

confidence: 99%

Section: Supplementary Informationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

et al. 2015

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Synthesis, Antiproliferative and Cytotoxic Activities, DNA Binding Features and Molecular Docking Study of Novel Enamine Derivatives

Gürdere

Aydın

Yencilek

et al. 2020

Chemistry & Biodiversity

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Novel enamine derivatives were synthesized from the reaction of lactone and chalcones and their antiproliferative and cytotoxic activities against six cancer cell lines (e. g., HeLa, HT29, A549, MCF7, PC3 and Hep3B) and one normal cell lines (e. g., FL) were investigated along with their mode of interactions with CT‐DNA. Most of the enamine derivatives with IC50 values of 86–168 μM demonstrated much stronger antiproliferative activity than the starting molecules against the cancer cells. While, among the enamine derivatives, four compounds displayed higher cytotoxic potency than the control drugs (5‐fluorouracil and cisplatin) against the Hep3B cell lines, these compounds did not exhibit any significant toxicity against normal cells, FL. The UV/VIS spectral data suggest that eight compounds cause hypochromism with a slight bathochromic shift (∼6 nm), indicating that they bind to the DNA by way of an intercalative or minor groove binding mode. The binding constants of the compounds are in the range of 0.1×103 M−1–2.3×104 M−1. The antiproliferative activity of studied enamine derivatives could possibly be due to their DNA binding as well as their cytotoxic properties. In addition to these assays, the chalcones and enamine derivatives were investigated by molecular docking to calculate the synergistic effect of antiproliferative activities against six human cancer cell lines.

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Sequential Two‐Step Stereoselective Amination of Allylic Alcohols through the Combination of Laccases and Amine Transaminases

2019

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A sequential two‐step chemoenzymatic methodology for the stereoselective synthesis of (3E)‐4‐(het)arylbut‐3‐en‐2‐amines in a highly selective manner and under mild reaction conditions is described. The approach consists of oxidation of the corresponding racemic alcohol precursors by the use of a catalytic system made up of the laccase from Trametes versicolor and the oxy‐radical TEMPO, followed by the asymmetric reductive bio‐transamination of the corresponding ketone intermediates. Optimisation of the oxidation reaction, exhaustive amine transaminase screening for the bio‐transaminations and the compatibility of the two enzymatic reactions were studied in depth in search of a design of a compatible sequential cascade. This synthetic strategy was successful and the combinations of enzymes displayed a broad substrate scope, with 16 chiral amines being obtained in moderate to good isolated yields (29–75 %) and with excellent enantiomeric excess values (94 to >99 %). Interestingly, both amine enantiomers can be achieved, depending on the selectivity of the amine transaminase employed in the system.

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Synthesis and anticancer activity of novel halolactones with β-aryl substituents from simple aromatic aldehydes

Cited by 47 publications

References 61 publications

Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

Synthesis, Antiproliferative and Cytotoxic Activities, DNA Binding Features and Molecular Docking Study of Novel Enamine Derivatives

Sequential Two‐Step Stereoselective Amination of Allylic Alcohols through the Combination of Laccases and Amine Transaminases

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