Synthesis and Chemical Properties of 3-Phosphono-coumarins and 1,2-Benzoxaphosphorins as Precursors for Bioactive Compounds

Koleva, Ana I.; Petkova, Nevena I.

doi:10.3390/molecules24112030

Cited by 13 publications

(16 citation statements)

References 82 publications

(123 reference statements)

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“…Recently, the synthesis of a large spectrum of coumarins and their derivatives has attracted attention in research and development to both medicinal and organic chemists due to their various biological activities like antitumor, antimicrobial, anti-HIV, serine protease inhibition, anti-cancer, antioxidant activity and vasorelaxant effect (Koleva et al 2019). Different pharmacological activities of coumarins mainly depend on the type of coumarin nucleus.…”

Section: Natural Antioxidantsmentioning

confidence: 99%

Antioxidants and antioxidant methods: an updated overview

2020

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Antioxidants had a growing interest owing to their protective roles in food and pharmaceutical products against oxidative deterioration and in the body and against oxidative stress-mediated pathological processes. Screening of antioxidant properties of plants and plant-derived compounds requires appropriate methods, which address the mechanism of antioxidant activity and focus on the kinetics of the reactions including the antioxidants. Many studies evaluating the antioxidant activity of various samples of research interest using different methods in food and human health have been conducted. These methods are classified, described, and discussed in this review. Methods based on inhibited autoxidation are the most suited for termination-enhancing antioxidants and for chain-breaking antioxidants, while different specific studies are needed for preventive antioxidants. For this purpose, the most common methods used in vitro determination of antioxidant capacity of food constituents were examined. Also, a selection of chemical testing methods was critically reviewed and highlighted. In addition, their advantages, disadvantages, limitations and usefulness were discussed and investigated for pure molecules and raw extracts. The effect and influence of the reaction medium on the performance of antioxidants are also addressed. Hence, this overview provides a basis and rationale for developing standardized antioxidant methods for the food, nutraceuticals, and dietary supplement industries. In addition, the most important advantages and shortcomings of each method were detected and highlighted. The chemical principles of these methods are outlined and critically discussed. The chemical principles of methods of 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulphonate) radical (ABTS •+ ) scavenging, 1,1-diphenyl-2-picrylhydrazyl (DPPH•) radical scavenging, Fe 3+ -Fe 2+ transformation assay, ferric reducing antioxidant power (FRAP) assay, cupric ions (Cu 2+ ) reducing power assay (Cuprac), Folin-Ciocalteu reducing capacity (FCR assay), peroxyl radical (ROO•), superoxide radical anion (O 2•− ), hydrogen peroxide (H 2 O 2 ) scavenging assay, hydroxyl radical (OH•) scavenging assay, singlet oxygen ( 1 O 2 ) quenching assay, nitric oxide radical (NO•) scavenging assay and chemiluminescence assay are outlined and critically discussed. Also, the general antioxidant aspects of main food components were discussed by a number of methods, which are currently used for the detection of antioxidant properties of food components. This review consists of two main sections. The first section is devoted to the main components in the food and pharmaceutical applications. The second general section comprises some definitions of the main antioxidant methods commonly used for the determination of the antioxidant activity of components. In addition, some chemical, mechanistic and kinetic basis, and technical details of the used methods are given.

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Section: Natural Antioxidantsmentioning

confidence: 99%

Antioxidants and antioxidant methods: an updated overview

2020

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“…This bond is reactive and chemically available; hence, it is possible to obtain coumarins modified at C-3 and C-4 and even larger fused coumarin heterocyclic derivatives. The Kumada, Stille, Heck, Sonogashira, Negishi, Suzuki, or Buchwald-Hartwig coupling reactions are most often used for this purpose [55][56][57][58][59][60][61][62][63]. The substrates in the abovementioned reactions are mostly coumarin derivatives such as vinyl coumarin, bromocoumarin, coumarin-3-carboxylic acid, or triflate-substituted coumarin.…”

Section: Scheme 3 Direct Synthesis Of Coumarins By C-h Bond Activatio...mentioning

confidence: 99%

Coumarins Synthesis and Transformation via C–H Bond Activation—A Review

Szwaczko

2022

Inorganics

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For several decades, coumarins have attracted considerable attention due to the fact of their application in diverse fields such as medical science and biomedical research as well as several industrial branches. Recently, many compounds containing the coumarin moiety have been intensively studied, mainly due to the fact of their biological activities such as antitumor, antioxidative, anti-HIV, vasorelaxant, antimicrobial, and anticancer. They are also widely used as fluorescent dyes and probes because of their great structural flexibility and large fluorescent quantum yields. For this reason, numerous attempts have been made to develop new and more practical methods for the synthesis of these compounds. This review aims at providing a comprehensive overview of coumarin synthesis methods by direct C–H bond activation in order to demonstrate the current state-of-the-art methods as well as the current limitations.

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“…The presence of the coumarin structure in natural products and biologically active molecules has promoted considerable interest toward their synthesis [ 1 , 2 , 3 ]. The coumarin framework is widely used as a building block for obtaining derivatives that exhibit a wide variety of biological properties [ 4 ], especially anti-HIV, antitumor, anticoagulant, and antibiotic activities [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions

Lyapchev

Koleva

et al. 2022

Molecules

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Quantum-chemical calculations on the spectral properties of some aryl substituted 3-phosphonocoumarins were performed, and the effect of the substituents in the aryl moiety was evaluated. The structures possessing promising fluorescent properties were successfully synthesized via Suzuki and Sonogashira cross-coupling. The synthetic protocol was also applied for the phosphorous chemoisomer of 3-phosphonocoumarin, 1,2-benzoxaphosphorin, and their carboxylate analogues. The optical properties of the arylated and alkynylated products were experimentally determined. The obtained quantum-chemical and experimental results give the possibility for a fine tuning of the optical properties of phosphorous-containing coumarin systems by altering the substituent at its C-6 position.

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Synthesis and Chemical Properties of 3-Phosphono-coumarins and 1,2-Benzoxaphosphorins as Precursors for Bioactive Compounds

Cited by 13 publications

References 82 publications

Antioxidants and antioxidant methods: an updated overview

Antioxidants and antioxidant methods: an updated overview

Coumarins Synthesis and Transformation via C–H Bond Activation—A Review

Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions

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