Novel enzymatic route for kinetic resolution of (±)1,4-benzodioxan-2-carboxylic acid

Kasture, Sangita M.; Varma, Rita; Kalkote, Uttam R.; Nene, Sanjay; Kulkarni, Bhaskar D.

doi:10.1016/j.bej.2005.06.014

Cited by 13 publications

(5 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, compared with R-(−)-doxazosin, S-(+)-doxazosin could offer reduced adverse effect including orthostatic hypotension, nausea, lethargy, fatigue and dizziness [6][7][8]. And the synthesis or biosynthesis of S-(+)-doxazosin and its intermediate have also been reported [9,10]. Stereoselective pharmacokinetics of the two enantiomers are still unclear.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective determination of doxazosin in human plasma by liquid chromatography–tandem mass spectrometry using ovomucoid chiral stationary phase

Liu

Zhong

Chen

2010

Journal of Chromatography B

View full text Add to dashboard Cite

Section: Introductionmentioning

confidence: 99%

Enantioselective determination of doxazosin in human plasma by liquid chromatography–tandem mass spectrometry using ovomucoid chiral stationary phase

Liu

Zhong

Chen

2010

Journal of Chromatography B

View full text Add to dashboard Cite

“…We earlier reported a transesterification method for synthesis of (S)-1 using ethyl acetate as solvent and acylating agent by Candida antartica, Novozyme A/S (Kasture et al 2005). In continuation of our effort to prepare enantiopure (S)-1 we studied the potential of various commercially available lipases of yeast and bacterial source, to selectively hydrolyze (±) 2, to give (S)-1 required for synthesis of the more effective (S)-doxazosin mesylate.…”

Section: Introductionmentioning

confidence: 99%

Lipases catalyzed enantioselective hydrolysis of (R,S)-methyl 1,4-benzodioxan-2-carboxylate intermediate for (S)-doxazosin mesylate

Varma

Kasture

Nene

et al. 2007

World J Microbiol Biotechnol

Self Cite

View full text Add to dashboard Cite

S)-1,4-benzodioxan-2-carboxylic acid-1 is used as starting compound for the production of the more effective (S) enantiomer of the drug doxazosin mesylate. The catalytic ability of some commercial lipases for preparations of (S) enantiomer of 1 from (±) methyl 1,4-benzodioxin-2-carboxylate-2 is reported. Lipases from bacterial sources were more successful in resolving the ester than those from the yeast lipases. About 85% enantiomerically pure ester was achieved by lipase from alcaligenes sp.

show abstract

“…Among them, optimal results were achieved via enzymatic resolutions of racemic 1,4‐benzodioxan‐2‐carboxylic acid or esters or by diastereomeric crystallization with the (+)‐dehydroabietylamine …”

Section: Introductionmentioning

confidence: 99%

“…Among them, optimal results were achieved via enzymatic resolutions of racemic 1,4-benzodioxan-2carboxylic acid or esters [20][21][22][23][24] or by diastereomeric crystallization with the (+)-dehydroabietylamine. 25 Pondering either yields and commercial availability, we followed the previously defined satisfactory method, in which the 1,4-benzodioxan-2-carboxylic acid was firstly resolved with the chiral dehydroabietylamine acetate and then converted into the methyl ester, affording crystallized (S)-II with high yield and high enantiomeric excess.…”

Section: Introductionmentioning

confidence: 99%

How do reaction conditions affect the enantiopure synthesis of 2‐substituted‐1,4‐benzodioxane derivatives?

et al. 2018

View full text Add to dashboard Cite

Several biologically active compounds structurally include the enantiopure 2-substituted-1,4-benzodioxane scaffold. The straightforward racemization that affects reactions involving most of the common chemical reactives is thus a crucial issue. The developing of a completely stereo-controlled synthetic route that does not affect the enantiomeric excess is consequently mandatory. It is also important to set up a reliable chiral HPLC method, able to follow the reaction, and to improve the synthetic performances. Here, we report the chiral investigation of two different synthons, we specifically evaluated the synthetic pathways that could be run in order to afford them, avoiding the racemization processes, which could normally occur in basic conditions. In addition, we developed peculiar chiral HPLC methods in order to resolve the enantiomers, define the enantiomeric excess, and fully characterize these compounds.

show abstract

Novel enzymatic route for kinetic resolution of (±)1,4-benzodioxan-2-carboxylic acid

Cited by 13 publications

References 11 publications

Enantioselective determination of doxazosin in human plasma by liquid chromatography–tandem mass spectrometry using ovomucoid chiral stationary phase

Enantioselective determination of doxazosin in human plasma by liquid chromatography–tandem mass spectrometry using ovomucoid chiral stationary phase

Lipases catalyzed enantioselective hydrolysis of (R,S)-methyl 1,4-benzodioxan-2-carboxylate intermediate for (S)-doxazosin mesylate

How do reaction conditions affect the enantiopure synthesis of 2‐substituted‐1,4‐benzodioxane derivatives?

Contact Info

Product

Resources

About