Isochaihulactone analogues: Synthesis and anti-proliferative activity of novel dibenzylbutyrolactones

Heidary, Hossein; Foroumadi, Alireza; Emami, Saeed; Khoobi, Mehdi; Panah, Fatemeh; Ardestani, Sussan K.; Shafiee, Abbas

doi:10.1016/j.ejmech.2010.09.064

Cited by 35 publications

(21 citation statements)

References 20 publications

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“…2), the H 11 -H 3 relationship of the syn-isomer is axial-equatorial and that of the anti-isomer is di-axial. Thus, the observed coupling constant between H 11 and H 3 of syn-isomer was lower than that of anti-isomer in accordance with the data reported in the literature [24].…”

Section: Chemistrysupporting

confidence: 94%

Synthesis of some novel pyrano[2,3-f]chromenone derivatives

et al. 2014

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Section: Chemistrysupporting

confidence: 94%

Synthesis of some novel pyrano[2,3-f]chromenone derivatives

et al. 2014

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“…isochaihulactone, parabenzlactone, phodophyllotoxin, etoposide). 41 On the other hand, some lignans with a piperonyl moiety, especially yatein, exhibit strong antifeedant properties against Tribolium confusum, Trogoderma granarium and Sitophilus granaries. 9,42 In our studies, in 13 cases of lactones with benzodioxol ring turned out to be good antifeedants.…”

Section: Relationship: Structure-activitymentioning

confidence: 99%

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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“…26 Moreover, the 1,3-benzodioxole system is present in various natural and synthetic biologically active compounds, which show antiproliferative, antiinflammatory or anticonvulsant properties. [27][28][29][30] …”

Section: Introductionmentioning

confidence: 98%