Green synthesis aspects of (R)-(-)-mandelic acid; a potent pharmaceutically active agent and its future prospects

Singh, Rahul Vikram; Sambyal, Krishika

doi:10.1080/07388551.2022.2109004

Cited by 10 publications

(3 citation statements)

References 57 publications

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“…31,41,47−51 In particular, (R)-mandelic acid is employed in the synthesis of antitumor and antiobesity drugs. 52,53 In this work, we have not only attempted to visually discriminate the enantiomeric pair of mandelic acid using a chiral organic receptor but have also been able to differentiate between them through morphological changes of the chiral composite, unveiling the ability of our material to distinguish at multiple platforms. Additionally, the critical role of intermolecular interactions was established through NMR, XPS, FTIR, and CD analysis, which, on collaborating with the DFT calculations, helped to clearly visualize the selective interactions that assisted in attaining the enantiomeric discrimination.…”

Section: ■ Introductionmentioning

confidence: 99%

Amino Acid-Based Molecular and Membranous Chiral Tools for Enantiomeric Recognition

Gambhir,

Kumar,

Murugesan

et al. 2024

Langmuir

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Given the need, both academic and industrial, for new approaches and technologies for chiral discrimination of enantiomers, the present work demonstrates the development through rational design and integration of two new chiral platforms (molecular and membranous) for enantioselective recognition through visual as well as microscopic observation. The molecular platform (TPT) is based on the tryptophan derivative developed through the condensation of two tryptophan units with terepthaloyl chloride. While TPT based on l-tryptophan recognizes R-mandelic acid over the S-isomer, the host with reverse chirality (TPDT) recognizes S-mandelic acid over R-isomer. The role of chemical functionality in this sensitive recognition process was established experimentally by developing an analogue of TPT and by judiciously using different chiral analytes. Importantly, a detailed theoretical study at the molecular level revealed the U-shaped conformation of TPT, creating a cavity for accommodating a chiral guest with selective functional interaction resulting in the discrimination of enantiomers. Finally, a chiral polymeric mat of poly(methyl methacrylate) (PMMA)/polyacrylonitrile (PAN) (2:3) impregnated with TPT was developed via electrospinning. The resulting fibrous mat was successfully utilized for chiral recognition through microscopic and architectural observation. Hence, the present work reports simple chiral tools for enantiomeric recognition.

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Section: ■ Introductionmentioning

confidence: 99%

Amino Acid-Based Molecular and Membranous Chiral Tools for Enantiomeric Recognition

Gambhir,

Kumar,

Murugesan

et al. 2024

Langmuir

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“…As one of the most important α-hydroxycarboxylic acids, mandelic acid (MA) extracted from almonds in the form of a racemic mixture, and enantioenriched mandelate and its derivatives are of particular interest due to their multipurpose applications and different biological performances. − For instance, ( S )-mandelate is often used as a chiral resolving or auxiliary reagent, while ( R )-mandelate is used for the production of antibiotics such as cephalosporins and semisynthetic penicillins (Figure , I and II). Meanwhile, cyclandelate and homatropine are used as anticoagulation and anticholinergic medications, respectively (Figure , III and IV). − Besides, mandelate derivatives can be readily transformed into other functionalized molecules, such as 1,2-diols, β-amino alcohols, and α-amino acid derivatives. Therefore, the use of pure enantiomeric mandelic acid and its derivatives in the study of their biofunctions and pharmacokinetics is critical in the organic and pharmaceutical industries. , …”

Section: Introductionmentioning

confidence: 99%

Enantiospecific Analysis of Carboxylic Acids Using Cinchona Alkaloid Dimers as Chiral Solvating Agents

Mo,

Wang,

Shen

et al. 2024

Anal. Chem.

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Cinchona alkaloid derivatives as Brønsted base catalysts have attracted considerable attention in the field of asymmetric catalysis. However, their potential application as chiral solvating agents has not been described. In this research, we investigated the use of the Cinchona alkaloid dimer, namely, (DHQ) 2 PHAL, as a chiral solvating agent for discerning various mandelic acid derivatives through 1 H NMR spectroscopy. The addition of catalytic amounts of DMAP facilitated this process. Our experimental results demonstrate that dimeric (DHQ) 2 PHAL exhibits remarkable chiral discrimination properties regarding the diagnostic split protons of 1 H NMR signals (including 24 examples, up to 0.321 ppm). Furthermore, it serves as an excellent chiral discriminating agent and provides good resolution for racemic chiral phosphoric acid as determined by 31 P NMR spectroscopy. The quality of enantiodifferentiation has also been evaluated by means of the parameter "resolution (R s )". Significantly, this class of CSAs based on (alkaloid) 2 linker systems with an azaaromatic linker can be directly employed, which is commercially available in an enantiopure form at very low cost and exhibits promising potential in determining the enantiopurity of α-hydroxy acids by chemoselective and biocatalytic reactions.

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“…(S)-mandelic acid (S-MA) is used for the synthesis of substituted cyclopentenones and commercial drugs, including non-steroidal anti-inflammatory drugs celecoxib and deracoxib [ 11 ], anticancer drugs, or anticoagulants [ 12 ]. Mandelic acid and its hydroxy derivatives have been quite well described in the literature [ 13 , 14 , 15 ]. However, there are few reports on mandelic acid salts and complexes with metals.…”

Section: Introductionmentioning

confidence: 99%

Research on the Electron Structure and Antimicrobial Properties of Mandelic Acid and Its Alkali Metal Salts

Świsłocka

Świderski

Nasiłowska

et al. 2023

IJMS

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This article investigated the structure, and the spectroscopic and antimicrobial properties of mandelic acid and its alkali metal salts. The electron charge distribution and aromaticity in the analyzed molecules were investigated using molecular spectroscopy methods (FT-IR, FT-Raman, 1H NMR, and 13C NMR) and theoretical calculations (structure, NBO, HOMO, LUMO, energy descriptors, and theoretical IR and NMR spectra). The B3LYP/6-311++G(d,p) method was used in the calculations. The antimicrobial activities of mandelic acid and its salt were tested against six bacteria: Gram-positive Listeria monocytogenes ATCC 13932, Staphylococcus aureus ATCC 25923, Bacillus subtilis ATCC 6633, and Loigolactobacillus backii KKP 3566; Gram-negative Escherichia coli ATCC 25922 and Salmonella Typhimurium ATCC 14028, as well as two yeast species, Rhodotorulla mucilaginosa KKP 3560 and Candida albicans ATCC 10231.

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Green synthesis aspects of (R)-(-)-mandelic acid; a potent pharmaceutically active agent and its future prospects

Cited by 10 publications

References 57 publications

Amino Acid-Based Molecular and Membranous Chiral Tools for Enantiomeric Recognition

Amino Acid-Based Molecular and Membranous Chiral Tools for Enantiomeric Recognition

Enantiospecific Analysis of Carboxylic Acids Using Cinchona Alkaloid Dimers as Chiral Solvating Agents

Research on the Electron Structure and Antimicrobial Properties of Mandelic Acid and Its Alkali Metal Salts

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