New stereoselective synthesis of thiamphenicol and florfenicol from enantiomerically pure cyanohydrin: a chemo-enzymatic approach

Lu, Weihong; Chen, Peiran; Lin, Guo‐Qiang

doi:10.1016/j.tet.2008.05.113

Cited by 57 publications

(32 citation statements)

References 29 publications

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“…In the literature, several approaches for the synthesis of florfenicol have been reported . But none of the reported procedures could be adopted as such because our requirement was for the [ S ‐methyl‐ 14 C]‐florfenicol.…”

Section: Resultsmentioning

confidence: 99%

A novel no‐carrier‐added submicromolar scale radiosynthesis of [S‐methyl‐¹⁴C]‐florfenicol

Srinivas

Prabhakar

Unny

et al. 2013

Labelled Comp Radiopharmac

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In this paper is reported a novel reaction scheme for the no-carrier-added submicromolar scale radiosynthesis of [S-methyl-(14)C]-florfenicol that has been newly designed, developed and employed by us successfully. The [(14)C]-product was obtained in an overall radiochemical yield of 30% based on [(14)C]-methyl iodide taken for the reaction with a radiochemical purity of more than 96%. The specific activity of the product was ~50 mCi (1.85 GBq)/mmol. Chlorosulfonation of compound I was followed by sodium salt formation in situ and it was succeeded by the introduction of [(14)C]-methyl group by coupling with [(14)C]-CH3 I. Subsequently, the oxazolidin-2-one protecting group was opened up by a reaction with sulfuric acid in dioxane and later, the amino group was dichloroacetylated with methyl-2,2-dichloroacetate in triethylamine to obtain [S-methyl-(14)C]-florfenicol.

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Section: Resultsmentioning

confidence: 99%

A novel no‐carrier‐added submicromolar scale radiosynthesis of [S‐methyl‐¹⁴C]‐florfenicol

Srinivas

Prabhakar

Unny

et al. 2013

Labelled Comp Radiopharmac

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“…Infrared spectroscopic analysis of the paeonol-β-CD complex was done, as per the literature [17]. Potassium bromide was used for tabletting.…”

Section: Methodsmentioning

confidence: 99%

Preparation of a Paeonol-Containing Temperature-Sensitive In Situ Gel and Its Preliminary Efficacy on Allergic Rhinitis

Chu

Chen

et al. 2013

IJMS

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In this paper, the optimal composition of a paeonol temperature-sensitive in situ gel composed of poloxamer 407 (P407) was determined, and a preliminary study of its effect on allergic rhinitis was performed. The optimal composition of the paeonol temperature-sensitive in situ gel included 2% paeonol inclusion, 22% P407, 2% poloxamer 188 (P188) and 2% PEG6000, as assessed by thermodynamic and rheological studies. The toad palate model was employed to study the toxicity of the paeonol temperature-sensitive in situ gel on the nasal mucosa. The result of this experiment showed low toxicity to cilia, which allows the gel to be used for nasal administration. The Franz diffusion cell method was used to study the in vitro release of paeonol and suggested that the in vitro release was in line with the Higuchi equation. This result suggests that the paeonol could be absorbed into the body through mucous membranes and had some characteristics of a sustained effect. Finally, the guinea pig model of ovalbumin sensitized allergic rhinitis was used to evaluate the preliminary efficacy of the gel, with the paeonol temperature-sensitive in situ gel showing a significant effect on the guinea pig model of sensitized allergic rhinitis (AR).

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“…[9][10][11] For example, the β-galactosyl ceramide, plakoside A, isolated from the marine sponge Plakortis simplex, was found to be a noncytotoxic immunosuppressant. [17][18][19][20][21][22][23][24][25][26][27] As part of our continuous work on the stereoselective synthesis of α-amino acid using chiral tricyclic iminolactone which is derived from natural (1R)-(＋)-camphor, [28][29][30][31][32][33][34][35][36][37] we successfully developed a concise and effective methodology to synthesize optically pure β-hydroxy-α-amino acid. [14,15] However, it is not an easy task to synthesize glycosphingolipids for extensive research purpose.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Synthesis of (−)‐Chloramphenicol, (+)‐Thiamphenicol and (+)‐Sphinganine via Chiral Tricyclic Iminolactone

2012

Chin. J. Chem.

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New stereoselective synthesis of thiamphenicol and florfenicol from enantiomerically pure cyanohydrin: a chemo-enzymatic approach

Cited by 57 publications

References 29 publications

A novel no‐carrier‐added submicromolar scale radiosynthesis of [S‐methyl‐¹⁴C]‐florfenicol

A novel no‐carrier‐added submicromolar scale radiosynthesis of [S‐methyl‐¹⁴C]‐florfenicol

Preparation of a Paeonol-Containing Temperature-Sensitive In Situ Gel and Its Preliminary Efficacy on Allergic Rhinitis

Stereoselective Synthesis of (−)‐Chloramphenicol, (+)‐Thiamphenicol and (+)‐Sphinganine via Chiral Tricyclic Iminolactone

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New stereoselective synthesis of thiamphenicol and florfenicol from enantiomerically pure cyanohydrin: a chemo-enzymatic approach

Cited by 57 publications

References 29 publications

A novel no‐carrier‐added submicromolar scale radiosynthesis of [S‐methyl‐14C]‐florfenicol

A novel no‐carrier‐added submicromolar scale radiosynthesis of [S‐methyl‐14C]‐florfenicol

Preparation of a Paeonol-Containing Temperature-Sensitive In Situ Gel and Its Preliminary Efficacy on Allergic Rhinitis

Stereoselective Synthesis of (−)‐Chloramphenicol, (+)‐Thiamphenicol and (+)‐Sphinganine via Chiral Tricyclic Iminolactone

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A novel no‐carrier‐added submicromolar scale radiosynthesis of [S‐methyl‐¹⁴C]‐florfenicol

A novel no‐carrier‐added submicromolar scale radiosynthesis of [S‐methyl‐¹⁴C]‐florfenicol