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Keywords = γ-alkylidenebutenolides

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8 pages, 1538 KiB  
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(Z)-5-(3′,4′-Bis(benzyloxy)benzylidene)furan-2(5H)-one
by Angelica Artasensi, Giovanna Baron, Giulio Vistoli, Giancarlo Aldini and Laura Fumagalli
Molbank 2021, 2021(1), M1193; https://doi.org/10.3390/M1193 - 28 Feb 2021
Cited by 4 | Viewed by 3246
Abstract
Over the years secondary metabolites have been considered as lead molecules both in their natural form and as templates for medicinal chemistry. Some secondary metabolites such as polyphenols and flavan-3-ols exert beneficial effects after a modification by the microbiota. Synthetic precursors of some [...] Read more.
Over the years secondary metabolites have been considered as lead molecules both in their natural form and as templates for medicinal chemistry. Some secondary metabolites such as polyphenols and flavan-3-ols exert beneficial effects after a modification by the microbiota. Synthetic precursors of some of these modified compounds, in turn, carried a γ-alkylidenebutenolide moiety which characterizes a large class of bioactive natural products endowed with a wide range of biological activities. For these reasons stereoselective preparation of γ-alkylidenebutenolide continues to be an important issue for organic chemists. Our objective is to synthetize the novel compound (Z)-5-(3′,4′-bis(benzyloxy)benzylidene)furan-2(5H)-one in a stereocontrolled-one-pot reaction. The product was obtained in good yield. Furthermore, the theoretical investigation of the transition states suggests a new procedure to achieve Z-isomer of β-unsubstituted γ-alkylidenebutenolide. Full article
(This article belongs to the Special Issue Innovative Approaches to Modify Polyphenols)
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11 pages, 5609 KiB  
Article
An Unusual Diterpene—Enhygromic Acid and Deoxyenhygrolides from a Marine Myxobacterium, Enhygromyxa sp.
by Tomohiko Tomura, Shiori Nagashima, Satoshi Yamazaki, Takashi Iizuka, Ryosuke Fudou and Makoto Ojika
Mar. Drugs 2017, 15(4), 109; https://doi.org/10.3390/md15040109 - 6 Apr 2017
Cited by 18 | Viewed by 5506
Abstract
Three new compounds, enhygromic acid (1) and deoxyenhygrolides A (2) and B (3), were isolated from a marine myxobacterium, Enhygromyxa sp. Compound 1 was found to be an acrylic acid derivative with a rare polycyclic carbon skeleton, [...] Read more.
Three new compounds, enhygromic acid (1) and deoxyenhygrolides A (2) and B (3), were isolated from a marine myxobacterium, Enhygromyxa sp. Compound 1 was found to be an acrylic acid derivative with a rare polycyclic carbon skeleton, decahydroacenaphthylene, by spectroscopic analyses. Compounds 2 and 3 were deoxy analogs of the known γ-alkylidenebutenolides, enhygrolides. Compound 1 exhibited cytotoxicity against B16 melanoma cells and anti-bacterial activity against Bacillus subtilis, and enhanced the NGF-induced neurite outgrowth of PC12 cells. Full article
(This article belongs to the Special Issue Marine Bioactive Natural Product Studies in Asia)
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16 pages, 193 KiB  
Article
Synthesis and Cytotoxic Activity of Some 3-Benzyl-5-Arylidenefuran-2(5H)-ones
by Róbson Ricardo Teixeira, Luiz Cláudio Barbosa, Célia Regina Alvares Maltha, Marcelo Eça Rocha, Daniel Pereira Bezerra, Letícia Veras Costa-Lotuf, Cláudia Pessoa and Manoel Odorico Moraes
Molecules 2007, 12(5), 1101-1116; https://doi.org/10.3390/12051101 - 24 May 2007
Cited by 42 | Viewed by 9391
Abstract
3-Benzyl-furan-2(5H)-one (2a) and 3-(4-bromobenzyl)-furan-2(5H)-one (2b) were treated with TBDMSOTf and converted into the corresponding tert-butyldimethyl-silylfuran ethers. These furans were further condensed with several aromatic aldehydes affording compounds 5-14 with general 3-benzyl-5-arylidene-furan-2(5H)-one structures in 31% to 98% yields. Such compounds are analogues of the [...] Read more.
3-Benzyl-furan-2(5H)-one (2a) and 3-(4-bromobenzyl)-furan-2(5H)-one (2b) were treated with TBDMSOTf and converted into the corresponding tert-butyldimethyl-silylfuran ethers. These furans were further condensed with several aromatic aldehydes affording compounds 5-14 with general 3-benzyl-5-arylidene-furan-2(5H)-one structures in 31% to 98% yields. Such compounds are analogues of the naturally occurring nostoclide lactones, reported to present moderate cytotoxic activity. Compounds 5-14 were submitted to an in vitro bioassay against the HL-60, HCT-8, SF295 and MDA-MB-435 cancer cell lines using the MTT cytotoxicity assay. Full article
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