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Finding the Right Way to Prepare Enantiopure Compounds: A Focus on Biologically Active Compounds. A Themed Honorary Issue to Prof. Richard M. Kellogg

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (15 September 2021) | Viewed by 5685

Special Issue Editors


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Guest Editor
Department of Drug Sciences, Medicinal Chemistry and Pharmaceutical Technology Section, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy
Interests: rational drug design, synthesis and structure–activity relationships of biologically active compounds (small molecules and peptides); preparation and characterization of chiral compounds; discovery of new modulators of sigma receptors as well as of small molecules able to affect the protein kinase C (PKC)/ELAV proteins/mRNA system
Special Issues, Collections and Topics in MDPI journals

E-Mail Website
Guest Editor
Department of Drug Sciences, Medicinal Chemistry and Pharmaceutical Technology Section, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy
Interests: design, synthesis, and characterization of biologically active compounds; structure–activity relationship studies including the role of chirality in the biological activity, with a particular focus on sigma receptor modulators and compounds targeting the protein kinase C (PKC)/ELAV proteins/mRNA system
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

We had the great pleasure of meeting Prof. Richard M. Kellogg about 20 years ago, during a meeting on chiral drugs. After his exciting lecture, we had a scientific conversation. Since then, we have always been in contact, and on several occasions we have taken advantage of his expertise and suggestions concerning the preparation of biologically active compounds in enantiopure forms.

Prof. Richard M. Kellogg was born and educated in the United States. After his Ph.D. at the University of Kansas, he moved to the Netherlands as a postdoctoral fellow and has remained there since. He was professor of organic chemistry at the University of Groningen from 1975 to 2002, where he and his group published works focusing on photochemistry, reactive intermediates, and bio-organic chemistry. More recently, he has worked on chirality, in particular on deracemization methods.

This honorary issue focuses on recent successes in the preparation of biologically active molecules in homochiral forms (deracemization methodologies, fractional crystallization, enantioselective HPLC) and on the assignment of absolute configuration.

Prof. Dr. Simona Collina
Dr. Daniela Rossi
Guest Editors

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Keywords

  • Deracemization methodologies
  • Fractional crystallization
  • Enantioselective HPLC
  • Absolute configuration

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Published Papers (2 papers)

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Research

12 pages, 1910 KiB  
Article
Enantioselective Synthesis of a New Non-Natural Gabosine
by Maximiliano Colobbio, Enrique Pandolfi and Valeria Schapiro
Molecules 2021, 26(5), 1423; https://doi.org/10.3390/molecules26051423 - 6 Mar 2021
Cited by 1 | Viewed by 2037
Abstract
The preparation of a new non-natural gabosine is reported, in which the chirality is transferred from the toluene’s biotransformed metabolite (1R,2S)-3-methylcyclohexa-3.5-diene-1,2-diol. Further chemical transformations to introduce additional functionality and chirality to the molecule were also accomplished. Full article
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15 pages, 3343 KiB  
Article
Enantiomeric Resolution and Absolute Configuration of a Chiral δ-Lactam, Useful Intermediate for the Synthesis of Bioactive Compounds
by Roberta Listro, Giacomo Rossino, Serena Della Volpe, Rita Stabile, Massimo Boiocchi, Lorenzo Malavasi, Daniela Rossi and Simona Collina
Molecules 2020, 25(24), 6023; https://doi.org/10.3390/molecules25246023 - 19 Dec 2020
Cited by 5 | Viewed by 2925
Abstract
During the past several years, the frequency of discovery of new molecular entities based on γ- or δ-lactam scaffolds has increased continuously. Most of them are characterized by the presence of at least one chiral center. Herein, we present the preparation, isolation and [...] Read more.
During the past several years, the frequency of discovery of new molecular entities based on γ- or δ-lactam scaffolds has increased continuously. Most of them are characterized by the presence of at least one chiral center. Herein, we present the preparation, isolation and the absolute configuration assignment of enantiomeric 2-(4-bromophenyl)-1-isobutyl-6-oxopiperidin-3-carboxylic acid (trans-1). For the preparation of racemic trans-1, the Castagnoli-Cushman reaction was employed. (Semi)-preparative enantioselective HPLC allowed to obtain enantiomerically pure trans-1 whose absolute configuration was assigned by X-ray diffractometry. Compound (+)-(2R,3R)-1 represents a reference compound for the configurational study of structurally related lactams. Full article
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