6.09 Synthesis of Esters and Lactones

Siengalewicz, Peter; Mulzer, Johann; Rinner, Uwe

doi:10.1016/b978-0-08-097742-3.00612-1

Cited by 21 publications

(19 citation statements)

References 320 publications

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“…First, lactones can be synthesized by the Baeyer–Villiger reaction, based on the exposure of ketones to peracids. The result is the inclusion of oxygen among alkyl or aryl substituents and carbonyl moieties, forming the corresponding ester [ 4 ]. Another method is halolactonization, where the ring is formed by the addition of oxygen and a halogen across a C=C double bond.…”

Section: Introductionmentioning

confidence: 99%

“…Another method is halolactonization, where the ring is formed by the addition of oxygen and a halogen across a C=C double bond. The halogen can then be removed by free radical hydrogenation [ 4 , 5 ]. The subsequent reaction that is applied in lactone synthesis is the Favorskii rearrangement [ 4 ].…”

Section: Introductionmentioning

confidence: 99%

“…The halogen can then be removed by free radical hydrogenation [ 4 , 5 ]. The subsequent reaction that is applied in lactone synthesis is the Favorskii rearrangement [ 4 ]. Additionally, there are a variety of microorganisms that can perform de novo biosynthesis of lactones, but enzymes are also known for the lactonization process [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

“…Additionally, there are a variety of microorganisms that can perform de novo biosynthesis of lactones, but enzymes are also known for the lactonization process [ 2 ]. Baeyer–Villiger oxidation has been applied in enzymatic protocols [ 4 ]. Two classes of enzymes are responsible for this reaction: Baeyer–Villiger monooxygenases (BVMOs) and hydrolases that follow the perhydrolase pathway.…”

Section: Introductionmentioning

confidence: 99%

“…In nature, cyclic esters are plant secondary metabolites that are connected with catabolic processes involving structurally related fatty acids and often possess low molecular weights [ 2 ]. They are responsible for the aroma of plants, among other features, and are often constituents of essential oils [ 3 , 4 ]. Natural lactones are mostly γ-lactones (in plants) and δ-lactones (in animals) [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

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Biological Activity of Selected Natural and Synthetic Terpenoid Lactones

Surowiak

Balcerzak

Lochyński

et al. 2021

IJMS

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Terpenoids with lactone moieties have been indicated to possess high bioactivity. Certain terpenoid lactones exist in nature, in plants and animals, but they can also be obtained by chemical synthesis. Terpenoids possessing lactone moieties are known for their cytotoxic, anti-inflammatory, antimicrobial, anticancer, and antimalarial activities. Moreover, one terpenoid lactone, artemisinin, is used as a drug against malaria. Because of these abilities, there is constant interest in new terpenoid lactones that are both isolated and synthesized, and their biological activities have been verified. In some cases, the activity of the terpenoid lactone is specifically connected to the lactone moiety. Recent works have revealed that new terpenoid lactones can demonstrate such functions and are thus considered to be potential active agents against many diseases.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Biological Activity of Selected Natural and Synthetic Terpenoid Lactones

Surowiak

Balcerzak

Lochyński

et al. 2021

IJMS

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Hybrid Compounds Containing a Ferrocene Scaffold as Potential Antimalarials

2021

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Malaria is an infectious disease, and it remains a serious health problem globally. The drugs developed for its treatment suffer from several shortcomings such as low water solubility, poor bioavailability, drug toxicity, and resistance. Molecular hybridization of different bioactive agents is a promising approach for developing hybrid compounds with improved therapeutic effects. Ferrocene, an organometallic, has been hybridized with several pharmacophores resulting in compounds with potent biological activities. In this research, a modified ferrocene scaffold was hybridized with selected pharmacophores. The synthesized compounds were characterized by Fourier‐Transform Infrared Spectroscopy (FTIR), Nuclear Magnetic Resonance Spectroscopy (NMR), and Liquid Chromatography‐Mass Spectroscopy. The hybrid compounds were obtained in good yields (53–76 %). In vitro evaluation against NF54 (drug‐sensitive) strain of Plasmodium falciparum parasites revealed the compounds, 16 and 19 (hybrids containing artesunate scaffold), together with 18 and 21 (hybrids containing oleanolic acid scaffold), as promising antimalarial agents. These compounds displayed IC50 values of 116.73±3.18, 56.33±15.20, 78.22±21.05, and 58.22±15.20 nM, respectively. These findings revealed the potency of ferrocene as a precursor for the development of promising antimalarials.

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An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate

Suchetti,

Foray,

Tempesti

et al. 2024

ChemistrySelect

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Hyperammonemia is a life‐threatening condition which can affect patients at any age. In pediatric patients, hyperammonemia can be caused by various acquired or inherited disorders such as urea cycle deficiencies or organic acidemias. Glycerol phenylbutyrate (GPB) is an orphan drug used in the treatment of hyperammonemia. GPB is a triglyceride composed of three phenylbutyric acid (PBA) molecules esterified to a glycerol molecule, which is synthesized through the acyl chloride route using thionyl chloride as an acylating agent. In this work we have developed an alternative synthesis method to obtain GPB directly under ambient conditions and avoiding the use of chlorinated solvents. Moreover, the use of carbodiimides as coupling agents, instead of thionyl chloride, allowed the conversion to the GPB in higher yields and with higher purity, without the need for column purification. We present a methodology that allows the production of GPB in a simple, efficient and environmentally and human health friendly way.

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6.09 Synthesis of Esters and Lactones

Cited by 21 publications

References 320 publications

Biological Activity of Selected Natural and Synthetic Terpenoid Lactones

Biological Activity of Selected Natural and Synthetic Terpenoid Lactones

Hybrid Compounds Containing a Ferrocene Scaffold as Potential Antimalarials

An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate

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