Chiral Pharmaceuticals

Tiritan, Maria Elizabeth; Ribeiro, Ana R.; Fernandes, Carla; Pinto, Madalena

doi:10.1002/0471238961.1608011823092009.a01.pub2

Cited by 19 publications

(20 citation statements)

References 181 publications

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“…Despite the fact that natural compounds possess pharmacological applications, their structures are limited to their production, and sometimes, comprise high levels of complexity, making them difficult to extract and purify, and even harder to synthesize. SAR studies are meant to determine the important moieties of natural compounds in order to improve their pharmacological/biological properties with smaller and simple molecules [88,89,90].…”

Section: Synthetic Cdxsmentioning

confidence: 99%

Chiral Derivatives of Xanthones with Antimicrobial Activity

et al. 2019

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According to the World Health Organization, the exacerbated use of antibiotics worldwide is increasing multi-resistant infections, especially in the last decade. Xanthones are a class of compounds receiving great interest in drug discovery and development that can be found as natural products or obtained by synthesis. Many derivatives of xanthones are chiral and associated with relevant biological activities, including antimicrobial. The aim of this review is to compile information about chiral derivatives of xanthones from natural sources and their synthesized examples with antimicrobial activity.

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Section: Synthetic Cdxsmentioning

confidence: 99%

Chiral Derivatives of Xanthones with Antimicrobial Activity

et al. 2019

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“…The chiral analysis by HPLC is based on a formation of transient diastereomeric complexes between the amino acids present in the hydrolysates and the chiral stationary phase (CSP) employed, being the less stable complex the first to elute [ 32 ]. There are several types of CSPs, such as polysaccharide-based, Pirkle-type, protein-based, macrocyclic antibiotic-based, crown ether-based, ligand exchange type, among others [ 33 , 34 , 35 ]; however, the last three types are the most used for the separation of primary amine-containing compounds and amino acids [ 36 , 37 ].…”

Section: Introductionmentioning

confidence: 99%

Marine Natural Peptides: Determination of Absolute Configuration Using Liquid Chromatography Methods and Evaluation of Bioactivities

et al. 2018

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Over the last decades, many naturally occurring peptides have attracted the attention of medicinal chemists due to their promising applicability as pharmaceuticals or as models for drugs used in therapeutics. Marine peptides are chiral molecules comprising different amino acid residues. Therefore, it is essential to establish the configuration of the stereogenic carbon of their amino acid constituents for a total characterization and further synthesis to obtain higher amount of the bioactive marine peptides or as a basis for structural modifications for more potent derivatives. Moreover, it is also a crucial issue taking into account the mechanisms of molecular recognition and the influence of molecular three-dimensionality in this process. In this review, a literature survey covering the report on the determination of absolute configuration of the amino acid residues of diverse marine peptides by chromatographic methodologies is presented. A brief summary of their biological activities was also included emphasizing to the most promising marine peptides. A case study describing an experience of our group was also included.

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“…In chiral drugs, knowledge about the stereochemistry is crucial and accompanies several steps of drug discovery and development. Thus, it can influence absorption, distribution, metabolism and excretion, as well as the molecular mechanism of action, through the phenomenon of chiral molecular recognition [2,4].…”

Section: Introductionmentioning

confidence: 99%

Chiral Separations in Preparative Scale: A Medicinal Chemistry Point of View

2020

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Enantiomeric separation is a key step in the development of a new chiral drug. Preparative liquid chromatography (LC) continues to be the technique of choice either during the drug discovery process, to achieve a few milligrams, or to a scale-up during the clinical trial, needing kilograms of material. However, in the last few years, instrumental and technical developments allowed an exponential increase of preparative enantioseparation using other techniques. Besides LC, supercritical fluid chromatography (SFC) and counter-current chromatography (CCC) have aroused interest for preparative chiral separation. This overview will highlight the importance to scale-up chiral separations in Medicinal Chemistry, especially in the early stages of the pipeline of drugs discovery and development. Few examples within different methodologies will be selected, emphasizing the trends in chiral preparative separation. The advantages and drawbacks will be critically discussed.

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Chiral Pharmaceuticals

Cited by 19 publications

References 181 publications

Chiral Derivatives of Xanthones with Antimicrobial Activity

Chiral Derivatives of Xanthones with Antimicrobial Activity

Marine Natural Peptides: Determination of Absolute Configuration Using Liquid Chromatography Methods and Evaluation of Bioactivities

Chiral Separations in Preparative Scale: A Medicinal Chemistry Point of View

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