A simple and eco-sustainable method for the<i>O</i>-Boc protection/deprotection of various phenolic structures under water-mediated/catalyst-free conditions

Cheraiet, Zinelaabidine; Hessainia, Sihem; Ouarna, Souad; Berredjem, Malika; Aouf, Nour‐Eddine

doi:10.1080/17518253.2012.738371

Cited by 23 publications

(8 citation statements)

References 24 publications

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“…The final step in the preparation of the copolymer precursor was the deprotection of the hydrazide functional groups (LC-NHNH 2 ) using a simple and effective procedure under mild conditions [ 32 ]. During this reaction, complete deprotection occurred as proved by NMR.…”

Section: Resultsmentioning

confidence: 99%

Polymer Nanomedicines with Ph-Sensitive Release of Dexamethasone for the Localized Treatment of Inflammation

et al. 2020

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Polymer-drug conjugates have several advantages in controlled drug delivery to inflammation as they can accumulate and release the drug in inflamed tissues or cells, which could circumvent the shortcomings of current therapy. To improve the therapeutic potential of polymer-drug conjugates in joint inflammation, we synthesized polymer conjugates based on N-(2-hydroxypropyl) methacrylamide) copolymers labeled with a near-infrared fluorescent dye and covalently linked to the anti-inflammatory drug dexamethasone (DEX). The drug was bound to the polymer via a spacer enabling pH-sensitive drug release in conditions mimicking the environment inside inflammation-related cells. An in vivo murine model of adjuvant-induced arthritis was used to confirm the accumulation of polymer conjugates in arthritic joints, which occurred rapidly after conjugate application and remained until the end of the experiment. Several tested dosage schemes of polymer DEX-OPB conjugate showed superior anti-inflammatory efficacy. The highest therapeutic effect was obtained by repeated i.p. application of polymer conjugate (3 × 1 mg/kg of DEX eq.), which led to a reduction in the severity of inflammation in the ankle by more than 90%, compared to 40% in mice treated with free DEX.

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Section: Resultsmentioning

confidence: 99%

Polymer Nanomedicines with Ph-Sensitive Release of Dexamethasone for the Localized Treatment of Inflammation

et al. 2020

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“…In general, this tunable Boc modification process was designed via a system thinking, including availability of raw lignin, economical/green modification, potentiality of drop-in-change to current thermoplastic processing, modification impact on microbial degradability/disposed environment at the end of use life; hence the holistic consideration makes this alternative method for upgrade of technical lignins very practical for future industrial application. Di-tert-butyl dicarbonate (Boc2O) is well known as a reagent for protection of amines and alcohols in organic synthesis in the presence of base catalyst [21][22][23]. In addition, it is also used as a dehydrating agent in reaction with carboxylic acids [24].…”

Section: Common Lignin Modification Strategiesmentioning

confidence: 99%

Tunable Boc modification of lignin and its impact on microbial degradation rate

Wang

et al. 2021

Sustainable Chemistry and Pharmacy

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A new type of modified lignin, lignin-p-Boc, was obtained through reaction with di-tert-butyl dicarbonate (Boc 2 O) in aqueous media catalyzed by 4-dimethylaminopyridine (DMAP). Boc modification occurred regardless of type of lignin, was tunable, and proceeded well in recovering lignin at high purity from sodium lignosulfonate (a common byproduct from pulping industry; lignin content: 60%). Lignin-p-BOC was demonstrated as a potential reactive filler in green plastic and as a potential crosslinker in design of bioresorbable composite polymeric implants. Furthermore, the effects of the modification on the breakdown rate of alkali lignin by microbes was investigated, and the results showed that the modification substantially decreases the breakdown rate. The tunable Boc modification process was designed via a system thinking, including availability of raw lignin, economical/green modification, potentiality of drop-in-change to current thermoplastic processing, modification impact on microbial degradability/disposed environment at the end of use life; hence the holistic consideration makes this alternative method for upgrade of technical lignins very practical for future industrial application. Via "in-situ" forming "easily breakable covalent bonds" with existing thermopolymers inside, Lignin-p-BOCs are also promising to play an important role as both excellent binders via "random match" and reductants in transforming linear plastic waste into circular plastics. File list (2) download file view on ChemRxiv V3 manuscript.pdf (515.26 KiB) download file view on ChemRxiv Supporting_Information_V2.pdf (2.33 MiB)

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“…Di-tert-butyl dicarbonate (Boc2O) is well known as a reagent for protection of amines and alcohols in organic synthesis in the presence of base catalyst. [21][22][23] In addition, it is also used as a dehydrating agent in reaction with carboxylic acids. 24 A recent revisited reaction of alcohols with Boc2O in the presence of 4-dimethylaminopyridine (DMAP) indicated that the pKa of the alcohols strongly affect formation of products (symmetrical carbonates or O-Boc) and the reaction rate;…”

Section: Scheme 2 Structure Of Lignin and A Postulated Modified Strumentioning

confidence: 99%

Tunable Boc modification of lignin and its impact on microbial degradation rate

Gu¹,

Wang²,

Li³

et al. 2020

Preprint

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A new type of modified lignin, lignin-p-Boc was obtained through reaction with di-tert-butyl dicarbonate in aqueous media. Boc modification occurred regardless of types of lignin, was tunable, and proceeded well in recovering lignin at high purity from sodium lignosulfonate. Further reactivity of Lignin-p-BOC was demonstrated as a potential reactive filler in green plastic and as potential crosslinker in design of bioresorbable composite polymeric implants. Furthermore, the effects of the modification on the breakdown rate of alkali lignin by microbial (white rot fungus P. chrysosporium) was investigated, and the results showed that the modification obviously decreased the breakdown rate. File list (2) download file view on ChemRxiv lignin manuscript V2.pdf (725.74 KiB) download file view on ChemRxiv Supporting_Information_V2.pdf (2.33 MiB)

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A simple and eco-sustainable method for theO-Boc protection/deprotection of various phenolic structures under water-mediated/catalyst-free conditions

Cited by 23 publications

References 24 publications

Polymer Nanomedicines with Ph-Sensitive Release of Dexamethasone for the Localized Treatment of Inflammation

Polymer Nanomedicines with Ph-Sensitive Release of Dexamethasone for the Localized Treatment of Inflammation

Tunable Boc modification of lignin and its impact on microbial degradation rate

Tunable Boc modification of lignin and its impact on microbial degradation rate

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