Anti-Helicobacter pylori activity of derivatives of the phthalide-containing antibacterial agents spirolaxine methyl ether, CJ-12,954, CJ-13,013, CJ-13,102, CJ-13,104, CJ-13,108 and CJ-13,015

Radcliff, Fiona J.; Fraser, John D.; Wilson, Zoe E.; Heapy, Amanda M.; Robinson, James E.; Bryant, Christina J.; Flowers, Christopher L.; Brimble, Margaret A.

doi:10.1016/j.bmc.2008.04.037

Cited by 23 publications

(6 citation statements)

References 12 publications

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“…The methallyl halide CM of commercially or readily available substrates 4a–h (Brimble et al, 2005 ) is well-catalyzed by IV ( Table 2 , Table S1 ). The reactions exhibit moderate selectivity ( E / Z , 1.7–4.6:1) in most cases, but the CM of methallyl bromide with both ketone 4d and silyl ether 4f affords the corresponding functionalized methallyl bromides 15d and 15f with poor selectivity ( Table S1 , entries 4 and 6).…”

Section: Resultsmentioning

confidence: 99%

Cross-Metathesis of Methallyl Halides: Concise Enantioselective Formal Total Synthesis of (–)-Presphaerene

et al. 2020

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The cross-metathesis (CM) of methallyl halides catalyzed using four different ruthenium-based complexes-Grubbs catalyst, Grubbs second-generation catalyst, Hoveyda-Grubbs second-generation catalyst, and Stewart-Grubbs catalyst-was investigated. When methallyl chloride or bromide was reacted with a model substrate containing a benzyl ether group, the Grubbs catalyst, and Grubbs second-generation catalyst did not promote the reaction well. However, the Hoveyda-Grubbs second-generation catalyst and Stewart-Grubbs catalyst afforded the corresponding products in moderate to good yield with moderate E/Z selectivity. Accordingly, several functionalized methallyl halides were prepared by CM. Various functional groups were well-tolerated in this system when the Stewart-Grubbs catalyst was used. To demonstrate the practical utility of our method, methallyl halide CM was successfully employed for the formal total synthesis of a natural product (-)presphaerene, in which the precursor of the key cyclopentanecarboxylate intermediate was efficiently prepared in three steps.

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Section: Resultsmentioning

confidence: 99%

Cross-Metathesis of Methallyl Halides: Concise Enantioselective Formal Total Synthesis of (–)-Presphaerene

et al. 2020

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“…These results are in accordance with previous reports. On the one hand, previous screening programme designed to discover active compounds against H. pylori allowed the isolation of seven phthalide antibiotics with specific anti-H. pylori activity (Dekker et al 1997;Radcliff et al 2008). On the other hand, the antiplasmodial activity of peperophthalide 1 (IC 50 8.5 μM) was found to be close to the antiplasmodial activity of the phthalide derivative Marilone 1, isolated from the sponge-derived fungus Stachylidium sp., with an IC 50 of 12.1 μM against P. berghei (Almeida et al 2011).…”

Section: Resultsmentioning

confidence: 99%

A new phthalide derivative from Peperomia nivalis

Vásquez-Ocmín

Haddad

Gadea

et al. 2016

Natural Product Research

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One new phthalide (1) was isolated from aerial parts of Peperomia nivalis, along with known compounds (2 and 3), reported in this species for the first time. The structure of the new compound was characterised on the basis of 1D (H and C NMR), 2D (COSY, HMQC, HMBC and NOESY) NMR and high-resolution mass spectral (HRMS) data. Compound 2 was isolated from a natural source for the first time but previously synthesised. Compounds 1-3 were evaluated for their anti-Helicobacter pylori and anti-Plasmodium falciparum activities. Compound 1 showed moderate activities against H. pylori (MIC 47.5 μM) and the F32-Tanzania strain of P. falciparum (IC 8.5 μM). Compounds 2 and 3 exhibited weak anti-H. pylori activity (MIC 241.3 and 237.6 μM, respectively) and were inactive against P. falciparum.

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“…Antibiotic phthalides from fungal sources and some synthetic analogues have been shown to be very effective and highly specific against H. pylori, and the presence of a spiroketal ring was shown to greatly enhance this activity. [46,47] While several known phthalide dimers from the family Apiaceae do contain a spiroketal ring, this occurs through a dimerisation process involving cyclisation of a butylidene phthalide side-chain, which is not present in monomeric sedanenolide, sedanolide or n-butylphthalide, which all have a saturated n-butyl side-chain.…”

Section: Discussionmentioning

confidence: 99%

A novel compound from celery seed with a bactericidal effect against <I>Helicobacter pylori</I>

et al. 2009

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Anti-Helicobacter pylori activity of derivatives of the phthalide-containing antibacterial agents spirolaxine methyl ether, CJ-12,954, CJ-13,013, CJ-13,102, CJ-13,104, CJ-13,108 and CJ-13,015

Cited by 23 publications

References 12 publications

Cross-Metathesis of Methallyl Halides: Concise Enantioselective Formal Total Synthesis of (–)-Presphaerene

Cross-Metathesis of Methallyl Halides: Concise Enantioselective Formal Total Synthesis of (–)-Presphaerene

A new phthalide derivative from Peperomia nivalis

A novel compound from celery seed with a bactericidal effect against <I>Helicobacter pylori</I>

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