Methods and approaches for determination and enantioseparation of (<i>RS</i>)‐propranolol

Batra, Sonika; Bhushan, Ravi

doi:10.1002/bmc.4370

Cited by 16 publications

(11 citation statements)

References 58 publications

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“…In 2021, Yang et al, listed [9] historically 70 β-adrenolytics (mostly with one stereogenic center) and presented a review for the enantioseparation of a few of them by supercritical fluid chromatography (SFC), simulated moving bed chromatography (SMB) and HPLC (mainly using eight types of CSPs) with no coverage of TLC. During 2018-19, Batra and Bhushan reviewed enantioseparation methods related only to atenolol [29] and only to propranolol [30] which covered direct approach using chiral columns, and TLC, and LC separation of their diastereomeric derivatives prepared by using different CDRs based on Marfey's reagent (MR) and CC.…”

Section: Application Of Hplcmentioning

confidence: 99%

′Ab Ovo′ Chiral Phases and Chiral Reagents for Liquid Chromatographic Separation and Isolation of Enantiomers

Bhushan

2022

The Chemical Record

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The de-novo approach of mixing chirally pure reagents or Cu(II)-L-amino acid complexes in the slurry of silica gel for preparing TLC plates was reported from author's laboratory and was successful for separation and isolation of enantiomers. Using high molar absorptivity molecules, e. g., 1,5-difluoro-2,4-dinitrobenzene and cyanuric chloride, more than 38 new chiral derivatizing reagents were synthesized in our laboratory by straightforward nucleophilic substitution with simple chiral auxiliaries. Besides, (S)-naproxen, (S)-ketoprofen, and (S)-levofloxacin were used as chiral platforms. A conceptual approach using both achiral phases in chromatography for enantioseparation was also adopted. 1 H NMR and DFT based software were used to explain structures of non-covalent and covalent diastereomeric pairs and determination of configuration and separation mechanism. The methods can be easily used to determine and control enantiomeric purity with advantages over a variety of commercial chiral phases.

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Section: Application Of Hplcmentioning

confidence: 99%

′Ab Ovo′ Chiral Phases and Chiral Reagents for Liquid Chromatographic Separation and Isolation of Enantiomers

Bhushan

2022

The Chemical Record

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“…Besides the formation of propranolol, two intermediate compounds 1a and 1b also were found. From the pristine propranolol, seven new derivatives have been synthesized from the compound (2) to (8), in which every compound of 3, 4, 5, and 6 produced only two isomers, different from the theory of 3 isomers (as shown in Table 1).…”

Section: Reaction Mechanisms Propranolol Has Been Synthesizedmentioning

confidence: 99%

“…Methods for the synthesis of propranolol were investigated by using enzymes to resolve intermediate compounds [8][9][10]. However, the enzyme strategy did not show effective manufacturing because of several limitations, i.e., multistep, low overall yields (lower than 30%), and use of hazardous and costly reagents [10,11].…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Propranolol and Novel Derivatives

Tran

Bạch

et al. 2020

Journal of Chemistry

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Propranolol is one of the first medications of the beta-blocker used for antihypertensive drugs. This study reports the facile route for the synthesis of propranolol and its novel derivatives. Herein, propranolol synthesis proceeded from 1-naphthol and isopropylamine under mild and less toxic conditions. Novel propranolol derivatives were designed by reactions of propranolol with benzoyl chloride, pyridinium chlorochromate, and n-butyl bromide through esterification, oxidation reduction, and alkylation, respectively. The isolation and purity of compounds were conducted using column chromatography and thin-layer chromatography. Mass spectrometry and 1H-NMR spectroscopy were applied to identify new compounds structure. Propranolol derivatives from 2-chlorobenzoyl chloride (compound 3), 2-fluorobenzoyl chloride (compound 5), and especially acetic anhydride (compound 6) manifested high yields and significantly increased water solubility. Six semisynthetic propranolol derivatives promise to improve antioxidative and biological activities.

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“…There is a numerically large number of molecules having a broad range of clinical applications occurring on a regular basis, under the group β ‐adrenolytics, which are sold under different brand names in different countries. There have appeared review articles on LC separation and determination and bioassay of enantiomers of atenolol (Batra & Bhushan, 2018) and propranolol (Batra & Bhushan, 2019). Enantioseparation of the two drugs by both direct and indirect approaches has been discussed, involving practical applications and assessment of several CSPs, CDRs, the use of chiral mobile phase additives and ligand exchange and impregnation methods.…”

Section: Case Studiesmentioning

confidence: 99%

Assessment and application of Marfey’s reagent and analogs in enantioseparation: a decade’s perspective

Sethi

Martens

Bhushan

2020

Biomedical Chromatography

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Of the various methods available for high-performance liquid chromatography separation of enantiomers (of e.g. amino acids and amino group containing compounds) by the pre-column derivatization approach, use of Marfey's reagent has been most successful with continued application since its introduction in 1984. The reagent is prepared from difluoro dinitro benzene by nucleophilic substitution of one of its F atoms by L-alanine amide. There is flexibility to prepare several chiral variants (by substituting the F atom with different chiral auxiliaries) and to tailor the hydrophobicity and resolution, ultimately, of the diastereomeric derivatives. The present paper assesses and reviews applications of Marfey's reagent and its chiral variants (i.e. other FDNP reagents) for enantioseparation of certain amino group containing drugs/amino acids, and to provide some case studies on enantiomeric separations that are important for the pharmaceutical industry. Various explanations for separation mechanism and elution order using FDNP reagents are included and the question of the configuration of the corresponding enantiomer using an indirect approach has also been addressed.

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Methods and approaches for determination and enantioseparation of (RS)‐propranolol

Cited by 16 publications

References 58 publications

′Ab Ovo′ Chiral Phases and Chiral Reagents for Liquid Chromatographic Separation and Isolation of Enantiomers

′Ab Ovo′ Chiral Phases and Chiral Reagents for Liquid Chromatographic Separation and Isolation of Enantiomers

Facile Synthesis of Propranolol and Novel Derivatives

Assessment and application of Marfey’s reagent and analogs in enantioseparation: a decade’s perspective

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