Synthesis of Antibiotic Stilbenes by Reductive Metalation of 3,4,5-Trimethoxybenzaldehyde Dimethyl Acetal

Azzena, Ugo; Idini, Maria Vittoria; Pilo, Luciano

doi:10.1081/scc-120018690

Cited by 9 publications

(6 citation statements)

References 16 publications

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“…3,5,6-Trimethylpyrazine-2-carbaldehyde 6 was prepared by the Pfitzner-Moffatt oxidation [20]. The intermediate 5 or 6 was converted to stilbene derivatives (A1-27) via Horner-Wadsworth-Emmons reaction [21]. The chemical structures of newly synthesized compounds were confirmed by IR, NMR, and ESI-MS.…”

Section: Resultsmentioning

confidence: 99%

Ligustrazine Derivatives. Part 4: Design, Synthesis, and Biological Evaluation of Novel Ligustrazine‐based Stilbene Derivatives as Potential Cardiovascular Agents

Deng¹,

Guo²,

Zhai³

et al. 2012

Chem Biol Drug Des

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A series of novel stilbene derivatives containing ligustrazinyl moiety was designed, synthesized, and assayed for their protective effects on damaged endothelial cells. The results showed that most ligustrazinyl stilbene derivatives exhibited high protective effects on the human umbilical vascular endothelial cells (HUVECs) damaged by hydrogen peroxide in comparison with Ligustrazine. The stilbene derivatives A6, A9, A11, A21, A24, A25, and A27 exhibited high potency with low EC 50 values ranged from 0.0249 lM to 0.0898 mM. Compound A27 displayed EC 50 0.0249 lM, which is 30 000 times higher than that of Ligustrazine, presenting a most promising lead for further investigation. Structure-activity relationships were briefly discussed.

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Section: Resultsmentioning

confidence: 99%

Ligustrazine Derivatives. Part 4: Design, Synthesis, and Biological Evaluation of Novel Ligustrazine‐based Stilbene Derivatives as Potential Cardiovascular Agents

Deng¹,

Guo²,

Zhai³

et al. 2012

Chem Biol Drug Des

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“…Acetal a was then subjected to a reductive metalation and alkylation to selectively replace the 4-methoxy group with an ethyl substituent. 45 After regeneration of the aldehyde moiety ( b ), oxidation with Oxone afforded carboxylic acid c , the structure of which was confirmed by X-ray crystallography. 46 Subsequent demethylation with boron tribromide gave d , which was smoothly reduced to the benzyl alcohol e by reaction with borane-dimethyl sulfide complex.…”

Section: Resultsmentioning

confidence: 89%

On the Nature of Guest Complexation in Water: Triggered Wetting–Water-Mediated Binding

et al. 2022

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The complexity of macromolecular surfaces means that there are still many open questions regarding how specific areas are solvated and how this might affect the complexation of guests. Contributing to the identification and classification of the different possible mechanisms of complexation events in aqueous solution, and as part of the recent SAMPL8 exercise, we report here on the synthesis and conformational properties of TEEtOA 2 , a cavitand with conformationally flexible ethyl groups at its portal. Using a combination of ITC and NMR spectroscopy, we report the binding affinities of a series of carboxylates to 2 and compare it to a related cavitand TEMOA 1 . Additionally, we report MD simulations revealing how the wetting of the pocket of 2 is controlled by the conformation of its rim ethyl groups and, correspondingly, a novel triggered wetting, guest complexation mechanism, whereby the approaching guest opens up the pocket of the host, inducing its wetting and ultimately allows the formation of a hydrated host–guest complex (H·G·H 2 O). A general classification of complexation mechanisms is also suggested.

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“…The molecule 9a had been obtained from 1 by Heck vinylation using 1-octene followed by a reduction of the double bond. 26 The porphyrin synthesis was made under modified Lindsey conditions. 27,28 The porphyrin 9a was then converted into the oxonaphthoporphyrin 10a via the Friedel-Crafts reaction sequence described by Callot.…”

Section: Synthesis Of Alkyl Substituted Oxonaphthoporphyrins (10a 10b)mentioning

confidence: 99%

Synthesis and characterization of π-extended porphyrins as potential precursors for the formation of columnar mesophases: Design principles for columnar mesophases need revision?

Herzog¹,

Neier²

2010

Arkivoc

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A series of meso-β bridged extended porphyrins substituted with long aliphatic chains were synthesized and fully characterized. Two different synthetic strategies were tested to obtain the target structures. The synthetic steps were optimized in order to obtain scalable routes for the production of sufficient quantities of π-extended porphyrins for material science studies. The porphyrins were obtained either as free bases or complexed with Ni II or Cu II . UV-Vis spectroscopy and polarized light microscopy was used for the analysis of the material properties of the π-extended porphyrins. The results obtained with our compounds are not compatible with the results reported in the literature.

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Synthesis of Antibiotic Stilbenes by Reductive Metalation of 3,4,5-Trimethoxybenzaldehyde Dimethyl Acetal

Cited by 9 publications

References 16 publications

Ligustrazine Derivatives. Part 4: Design, Synthesis, and Biological Evaluation of Novel Ligustrazine‐based Stilbene Derivatives as Potential Cardiovascular Agents

Ligustrazine Derivatives. Part 4: Design, Synthesis, and Biological Evaluation of Novel Ligustrazine‐based Stilbene Derivatives as Potential Cardiovascular Agents

On the Nature of Guest Complexation in Water: Triggered Wetting–Water-Mediated Binding

Synthesis and characterization of π-extended porphyrins as potential precursors for the formation of columnar mesophases: Design principles for columnar mesophases need revision?

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