An Overview of Cinchona Alkaloids in Chemistry

Song, Choong Eui

doi:10.1002/9783527628179.ch1

Cited by 35 publications

(34 citation statements)

References 34 publications

(19 reference statements)

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“…35 Unlike other natural products employed herein, quinine is composed of two discrete ring systems; however, the stereochemical complexity and diverse functionality (a tertiary amine, a secondary alcohol, an olefin, and a quinoline) of quinine make it amenable to selective ring system distortion to create diverse molecular scaffolds (Figure 4, Q1–Q5 ).…”

Section: Resultsmentioning

confidence: 99%

A ring-distortion strategy to construct stereochemically complex and structurally diverse compounds from natural products

Huigens

Morrison²,

Hicklin³

et al. 2013

Nature Chem

281

248

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High-throughput screening is the dominant method to identify lead compounds in drug discovery. As such, the makeup of screening libraries will largely dictate the biological targets that can be modulated and the therapeutics that can be developed. Unfortunately, most compound screening collections consist principally of planar molecules with little structural or stereochemical complexity, compounds that do not offer the arrangement of chemical functionality necessary for modulation of many drug targets. Here we describe a novel, general, and facile strategy for the creation of diverse compounds with high structural and stereochemical complexity using readily available natural products as synthetic starting points. We show, through evaluation of chemical properties including fraction of sp3 carbons, ClogP, and the number of stereogenic centers, that these compounds are significantly more complex and diverse than those in standard screening collections, and guidelines are given for the application of this strategy to any suitable natural product.

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Section: Resultsmentioning

confidence: 99%

A ring-distortion strategy to construct stereochemically complex and structurally diverse compounds from natural products

Huigens

Morrison²,

Hicklin³

et al. 2013

Nature Chem

281

248

View full text Add to dashboard Cite

show abstract

“…QN, the active ingredient of antimalarial pharmaceuticals, was isolated in 1820 and, since then, has played a crucial role in medical treatment of malaria for over 300 years. [2] Later it was replaced by new compounds such as chloroquinine; however, it is again applied against resistant strains nowadays. QN has been also used in the food and beverages industry as a bitter additive (e.g.…”

Section: Introductionmentioning

confidence: 99%

Vibrational analysis of cinchona alkaloids in the solid state and aqueous solutions

Roman

Chruszcz‐Lipska

Barańska

2015

J Raman Spectroscopy

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Cinchona alkaloids are well-known antimalarial compounds also used in asymmetric synthesis in organic chemistry. In this work, vibrational spectra of quinine, quinidine, cinchonine, and cinchonidine were acquired and interpreted on the basis of theoretical calculations. Normal Raman spectra of the alkaloids in solution exhibit similar patterns and cannot be used for differentiation between the derivatives (e.g. quinine and cinchonidine) and corresponding pseudoenantiomers (e.g. quinine and quinidine). Thus, Raman Optical Activity (ROA) method was applied to show distinct differences related to the configuration of chiral atoms. ROA allowed unequivocal identification of the pseudoenantiomers based on the sign of the characteristic bands from a single measurement. The experiments were supported by the theoretical approach including conformational study followed by wavenumber calculations and Potential Energy Distribution (PED) analysis. For quinine, vibrational spectroscopy was additionally used to show its structural changes in aqueous solutions at various pH and its distribution in a pharmaceutical product. Spatial distribution of quinine in a drug was observed by the FT-Raman mapping technique.

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“…The drug is also used for the treatment of muscle cramps and reversal of multidrug resistance during chemotherapy. In food and beverage industries, it is applied as a bitter flavoring agent in tonic water or tonic-containing mixed beverages [1][2][3].…”

Section: Introductionmentioning

confidence: 99%

“…1) is an important plant alkaloid isolated from the bark of cinchona, a plant of South America. Historically, it has been used as an important antimalarial drug for more than 300 years [1]. The drug is also used for the treatment of muscle cramps and reversal of multidrug resistance during chemotherapy.…”

Section: Introductionmentioning

confidence: 99%

Polymer-modified glassy carbon electrode for the electrochemical detection of quinine in human urine and pharmaceutical formulations

et al. 2012

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An Overview of Cinchona Alkaloids in Chemistry

Cited by 35 publications

References 34 publications

A ring-distortion strategy to construct stereochemically complex and structurally diverse compounds from natural products

A ring-distortion strategy to construct stereochemically complex and structurally diverse compounds from natural products

Vibrational analysis of cinchona alkaloids in the solid state and aqueous solutions

Polymer-modified glassy carbon electrode for the electrochemical detection of quinine in human urine and pharmaceutical formulations

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