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Search Results (10)

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Authors = Cosimo Cardellicchio ORCID = 0000-0002-6830-1091

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10 pages, 1355 KiB  
Article
Alternative HPLC-DAD Direct-Phase Approach to Measurement of Enantiopurity of Lactic Acid Derivatives
by Maria Montrone, Cosimo Cardellicchio and Maria Annunziata M. Capozzi
Appl. Sci. 2025, 15(12), 6433; https://doi.org/10.3390/app15126433 - 7 Jun 2025
Viewed by 685
Abstract
Lactic acid (LA) is a natural organic acid that can be used in a wide variety of industries. Recently, the production of lactic acid by fermentation protocols has gained relevance. However, these biotechnological processes often encounter challenges in the production of enantiopure D- [...] Read more.
Lactic acid (LA) is a natural organic acid that can be used in a wide variety of industries. Recently, the production of lactic acid by fermentation protocols has gained relevance. However, these biotechnological processes often encounter challenges in the production of enantiopure D- or L-lactic acid. Thus, the measurement and control of the enantiopurity of lactic acid and its derivatives is a crucial step in these productions, especially when monomers have to be used to synthesize polymers, such as polylactic acid (PLA). In the present work, we propose a measurement of the enantiopurity of lactic acid mixtures with HPLC-DAD by using direct-phase conditions, which are mild, and a large set of different employable chiral columns. To this end, we report the synthesis of two new LA derivatives (2-nitrobenzyl 2-hydroxypropanoate and 2,4-dinitrobenzyl 2-hydroxypropanoate) and benzyl 2-hydroxypropanoate, with a selective and non-racemizing chemical functionalization. Then, three commercially available HPLC direct-phase chiral columns are tested to achieve a method for measuring the enantiomeric purity of lactic acid derivatives. The 2-nitrobenzyl lactate was chosen as the best lactic acid derivative and the Chiralpak IA column was chosen as the most effective chiral column to achieve a new and efficient protocol (Rs = 3.57 and α = 1.13) for the measurement of the enantiopurity of lactic acid. Full article
(This article belongs to the Section Chemical and Molecular Sciences)
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2 pages, 450 KiB  
Correction
Correction: Mallamaci et al. Antiproliferative Activity of Aminobenzylnaphthols Deriving from the Betti Reaction. Appl. Sci. 2022, 12, 7779
by Rosanna Mallamaci, Maria Annunziata M. Capozzi and Cosimo Cardellicchio
Appl. Sci. 2024, 14(24), 11615; https://doi.org/10.3390/app142411615 - 12 Dec 2024
Viewed by 510
Abstract
In the original publication [...] Full article
(This article belongs to the Special Issue Advances in the Synthesis of Biologically Important Intermediates/Drugs)
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8 pages, 2176 KiB  
Article
Synthesis and Preliminary Screening of the Biological Activity of Sulindac Sulfoximine Derivatives
by Cosimo Cardellicchio, Valentino Laquintana, Rosa Maria Iacobazzi, Nunzio Denora, Antonio Scilimati, Maria Grazia Perrone and Maria Annunziata M. Capozzi
Appl. Sci. 2023, 13(21), 12002; https://doi.org/10.3390/app132112002 - 3 Nov 2023
Viewed by 1933
Abstract
Sulindac is a well-known anti-inflammatory agent, sometimes employed as an adjuvant in antitumor therapy. Due to the recent interest in sulfoximine for its potential chemotherapeutics, we decided to transform sulindac and its methyl ester into the corresponding sulfoximines to test their antitumor activity. [...] Read more.
Sulindac is a well-known anti-inflammatory agent, sometimes employed as an adjuvant in antitumor therapy. Due to the recent interest in sulfoximine for its potential chemotherapeutics, we decided to transform sulindac and its methyl ester into the corresponding sulfoximines to test their antitumor activity. These compounds were fully characterized. Eventually, sulindac, sulindac methyl ester and the two novel corresponding sulfoximines were tested against malignant cells of U-87 glioblastoma, MCF-7 human breast cancer, HepG2 human liver hepatocellular carcinoma, CaCo-2 human colon cancer, and HeLa human cervical cancer. Interesting preliminary results were observed that encourage new investigations in this research theme. Full article
(This article belongs to the Section Chemical and Molecular Sciences)
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5 pages, 985 KiB  
Short Note
1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-trifluoromethanesulfonate
by Cosimo Cardellicchio and Maria Annunziata M. Capozzi
Molbank 2023, 2023(3), M1695; https://doi.org/10.3390/M1695 - 14 Jul 2023
Cited by 1 | Viewed by 1804
Abstract
The complex structure of aminobenzylnaphthols can be easily obtained with the useful Betti reaction. These valuable compounds can give rise to chiral intermediates, that found wide application in asymmetric synthesis. 1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-ol 1 was treated with triflic anhydride to yield [...] Read more.
The complex structure of aminobenzylnaphthols can be easily obtained with the useful Betti reaction. These valuable compounds can give rise to chiral intermediates, that found wide application in asymmetric synthesis. 1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-ol 1 was treated with triflic anhydride to yield the corresponding (S,S)-triflate 2, which is a valuable intermediate in the future synthesis of aminophosphine, to be used in asymmetric catalysis. Preliminarily structural considerations based upon H(1)-NMR spectroscopy are also reported. Full article
(This article belongs to the Collection Molecules from Catalytic Processes)
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1 pages, 422 KiB  
Correction
Correction: Capozzi, M.A.M.; Cardellicchio, C. (S,S)-2-(((Hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic Acid Methyl Ester. Molbank 2022, 2022, M1528
by Maria Annunziata M. Capozzi and Cosimo Cardellicchio
Molbank 2023, 2023(2), M1631; https://doi.org/10.3390/M1631 - 24 Apr 2023
Viewed by 991
Abstract
In the original publication [...] Full article
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4 pages, 642 KiB  
Short Note
(S,S)-2-(((Hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic Acid Methyl Ester
by Maria Annunziata M. Capozzi and Cosimo Cardellicchio
Molbank 2022, 2022(4), M1528; https://doi.org/10.3390/M1528 - 15 Dec 2022
Cited by 2 | Viewed by 1810 | Correction
Abstract
The solvent-free Betti reaction of 2-naphthol, 4-nitrobenzaldehyde and (S)-valine methyl ester gave the corresponding aminobenzylnaphthol of the (S,S)-2-(((hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic acid methyl ester in good yield (59%). This product was fully characterized. We observed that the racemization that occurs [...] Read more.
The solvent-free Betti reaction of 2-naphthol, 4-nitrobenzaldehyde and (S)-valine methyl ester gave the corresponding aminobenzylnaphthol of the (S,S)-2-(((hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic acid methyl ester in good yield (59%). This product was fully characterized. We observed that the racemization that occurs in some Betti reactions with (S)-valine methyl ester was absent in this reaction, and thus the predominant (S,S)-product was obtained. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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4 pages, 686 KiB  
Short Note
(S,S)-1-(Phenyl((1′-4-nitrophenyl-ethyl)amino)methyl)-2-naphthol
by Maria Annunziata M. Capozzi and Cosimo Cardellicchio
Molbank 2022, 2022(4), M1522; https://doi.org/10.3390/M1522 - 8 Dec 2022
Cited by 3 | Viewed by 1531
Abstract
The Betti reaction of 2-naphthol, benzaldehyde and (S)-1-(4-nitrophenyl)ethylamine without any solvent gave the corresponding aminobenzylnaphthol, that is the (S,S)-1-(phenyl((1′-4-nitrophenyl-ethyl)amino)methyl)-2-naphthol, in good yield (56%). The absolute configuration of the title compound was attributed by NMR analysis, a procedure [...] Read more.
The Betti reaction of 2-naphthol, benzaldehyde and (S)-1-(4-nitrophenyl)ethylamine without any solvent gave the corresponding aminobenzylnaphthol, that is the (S,S)-1-(phenyl((1′-4-nitrophenyl-ethyl)amino)methyl)-2-naphthol, in good yield (56%). The absolute configuration of the title compound was attributed by NMR analysis, a procedure that is reliable if compared with the data obtained by X-ray diffraction experiments. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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11 pages, 4133 KiB  
Article
Antiproliferative Activity of Aminobenzylnaphthols Deriving from the Betti Reaction
by Rosanna Mallamaci, Maria Annunziata M. Capozzi and Cosimo Cardellicchio
Appl. Sci. 2022, 12(15), 7779; https://doi.org/10.3390/app12157779 - 2 Aug 2022
Cited by 8 | Viewed by 2246 | Correction
Abstract
Two aminobenzylnaphthols, which are representative items of the family of compounds synthesized with the Betti reaction, were investigated as antiproliferative agents against adenocarcinoma human colorectal (Caco-2) and human neuroblastoma (SH-SY5Y) cell lines, using cisplatin as a positive control. A better antiproliferative activity was [...] Read more.
Two aminobenzylnaphthols, which are representative items of the family of compounds synthesized with the Betti reaction, were investigated as antiproliferative agents against adenocarcinoma human colorectal (Caco-2) and human neuroblastoma (SH-SY5Y) cell lines, using cisplatin as a positive control. A better antiproliferative activity was recorded after 24 h of incubation for the first tested molecule, whereas the other one was more effective after 72 h of incubation. These results support the hypothesis that both of the tested aminobenzylnaphthols could potentially be endowed with a biological activity. Full article
(This article belongs to the Special Issue Advances in the Synthesis of Biologically Important Intermediates/Drugs)
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Graphical abstract

13 pages, 1316 KiB  
Communication
Stereoselective Chemoenzymatic Synthesis of Optically Active Aryl-Substituted Oxygen-Containing Heterocycles
by Paola Vitale, Antonia Digeo, Filippo Maria Perna, Gennaro Agrimi, Antonio Salomone, Antonio Scilimati, Cosimo Cardellicchio and Vito Capriati
Catalysts 2017, 7(2), 37; https://doi.org/10.3390/catal7020037 - 25 Jan 2017
Cited by 15 | Viewed by 5863
Abstract
A two-step stereoselective chemoenzymatic synthesis of optically active α-aryl-substituted oxygen heterocycles was developed, exploiting a whole-cell mediated asymmetric reduction of α-, β-, and γ-chloroalkyl arylketones followed by a stereospecific cyclization of the corresponding chlorohydrins into the target heterocycles. Among the various whole cells [...] Read more.
A two-step stereoselective chemoenzymatic synthesis of optically active α-aryl-substituted oxygen heterocycles was developed, exploiting a whole-cell mediated asymmetric reduction of α-, β-, and γ-chloroalkyl arylketones followed by a stereospecific cyclization of the corresponding chlorohydrins into the target heterocycles. Among the various whole cells screened (baker’s yeast, Kluyveromyces marxianus CBS 6556, Saccharomyces cerevisiae CBS 7336, Lactobacillus reuteri DSM 20016), baker’s yeast was the one providing the best yields and the highest enantiomeric ratios (up to 95:5 er) in the bioreduction of the above ketones. The obtained optically active chlorohydrins could be almost quantitatively cyclized in a basic medium into the corresponding α-aryl-substituted cyclic ethers without any erosion of their enantiomeric integrity. In this respect, valuable, chiral non-racemic functionalized oxygen containing heterocycles (e.g., (S)-styrene oxide, (S)-2-phenyloxetane, (S)-2-phenyltetrahydrofuran), amenable to be further elaborated on, can be smoothly and successfully generated from their prochiral precursors. Full article
(This article belongs to the Special Issue Asymmetric and Selective Biocatalysis)
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Graphical abstract

12 pages, 353 KiB  
Article
Bioactivity of a Family of Chiral Nonracemic Aminobenzylnaphthols towards Candida albicans
by Maria Annunziata M. Capozzi, Cosimo Cardellicchio, Angela Magaletti, Antonio Bevilacqua, Marianne Perricone and Maria Rosaria Corbo
Molecules 2014, 19(4), 5219-5230; https://doi.org/10.3390/molecules19045219 - 23 Apr 2014
Cited by 12 | Viewed by 5538
Abstract
Chiral nonracemic aminobenzylnaphthols were obtained by a Betti multi-component reaction between 2-naphthol, aryl aldehydes and enantiopure arylethylamine. Moreover, some new aminobenzylnaphthols were synthesized by a similar reaction between 2-naphthol, aryl aldehydes and prolinol. These aminobenzylnaphthols, synthesized from different components and thus having different [...] Read more.
Chiral nonracemic aminobenzylnaphthols were obtained by a Betti multi-component reaction between 2-naphthol, aryl aldehydes and enantiopure arylethylamine. Moreover, some new aminobenzylnaphthols were synthesized by a similar reaction between 2-naphthol, aryl aldehydes and prolinol. These aminobenzylnaphthols, synthesized from different components and thus having different structural features, were tested as anti-yeast agents inhibiting Candida albicans. The effect towards the test strain was studied with a microdilution approach and three different concentrations (150, 300 and 450 µg/mL) were tested. The best results were found for the aminobenzylnaphthols obtained from 1-naphthylethylamine and from natural prolinol. The use of the two-way ANOVA highlighted the better performances of the prolinol derivative among the differently structured aminobenzylnaphthols that were screened. The activity towards C. albicans of this prolinol derivative resulted to be interesting and could represent a promising alternative to overcome the problem of the strains resistant to the traditional antifungals. Full article
(This article belongs to the Special Issue Parallel Synthesis)
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