An Improved Synthesis of 4-Chlorocoumarin-3-sulfonyl Chloride and Its Reactions with Different Bidentate Nucleophiles to Give Pyrido[1',2':2,3]- and Thiazino[3',2':2,3]-1,2,4-Thiadiazino[6,5-c]Benzopyran-6-one 7,7-Dioxides

Jashari, Ahmed; Hey‐Hawkins, Evamarie; Mikhova, B.M.; Draeger, Gerald; Popovski, Emil

doi:10.3390/12082017

Cited by 14 publications

(8 citation statements)

References 24 publications

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“…The synthetic procedure involved derivatization of the appropriate heterocyclic amines to obtain diazonium ions, which were further used as electrophiles to a ack the coumarine ring (29). This procedure has already been described in detail in a previous study (18).…”

Section: Synthetic Procedures and Characterization Of Synthesized Compmentioning

confidence: 99%

Potential antiproliferative effect of isoxazolo- and thiazolo coumarin derivatives on breast cancer mediated bone and lung metastases

et al. 2015

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Potential antiproliferative effect of isoxazolo-and thiazolo coumarin derivatives on breast cancer mediated bone and lung metastasesThe study highlights the current progress in the development of coumarin scaffolds for drug discovery as novel anticancer agents in metastatic breast cancer. Eight compounds, combining the coumarin core and five membered heterocycles (isoxazoles and thiazoles) in hydrazinyldiene--chroman-2,4-diones, were characterized in terms of a potential antiproliferative effect on bone (SCP1833) and lung (SCP4175) metastatic breast cancer cell lines using the 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide assay. Cell viability was evaluated after 48 and 72 h of treatment and the 50 % inhibitory concentrations were determined. The results demonstrated dose-and time-dependent activity, with the most potent molecules having a thiazole moiety, without or with additional methyl group(s) attached to the carbon(s) at position(s) 5 and/or 4 in the thiazole ring. These molecules possessed significantly higher potency against both test cell lines compared to 4-hydroxycoumarin.

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Section: Synthetic Procedures and Characterization Of Synthesized Compmentioning

confidence: 99%

Potential antiproliferative effect of isoxazolo- and thiazolo coumarin derivatives on breast cancer mediated bone and lung metastases

et al. 2015

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“…The ability to exert and manifest multiple anti-HIV activities as well as having the potential to overcome persistent resistance is a prominent property of coumarin and its derivatives [4,34]. Hybridization of molecules involves the combination of more than one pharmacophore to produce one hybrid compound that could inhibit HIV by single or multiple mechanisms and counterbalance the side effects that manifest because of the usage of a particular compound, or different hybrids that provide a novel anti-HIV activity with a much better result [4,36].…”

Section: Bibliometric Analysismentioning

confidence: 99%

Recent Progress in Synthesis, POM Analyses and SAR of Coumarin-Hybrids as Potential Anti-HIV Agents—A Mini Review

Suleiman,

Almalki,

Ben Hadda

et al. 2023

Pharmaceuticals

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The human immunodeficiency virus (HIV) is the primary cause of acquired immune deficiency syndrome (AIDS), one of the deadliest pandemic diseases. Various mechanisms and procedures have been pursued to synthesise several anti-HIV agents, but due to the severe side effects and multidrug resistance spawning from the treatment of HIV/AIDS using highly active retroviral therapy (HAART), it has become imperative to design and synthesise novel anti-HIV agents. Literature has shown that natural sources, particularly the plant kingdom, can release important metabolites that have several biological, mechanistic and structural representations similar to chemically synthesised compounds. Certainly, compounds from natural and ethnomedicinal sources have proven to be effective in the management of HIV/AIDS with low toxicity, fewer side effects and affordability. From plants, fungi and bacteria, coumarin can be obtained, which is a secondary metabolite and is well known for its actions in different stages of the HIV replication cycle: protease, integrase and reverse transcriptase (RT) inhibition, cell membrane fusion and viral host attachment. These, among other reasons, are why coumarin moieties will be the basis of a good building block for the development of potent anti-HIV agents. This review aims to outline the synthetic pathways, structure–activity relationship (SAR) and POM analyses of coumarin hybrids with anti-HIV activity, detailing articles published between 2000 and 2023.

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“…Table 3 shows fluorescent coumarin sulfonyl chlorides used for labelling biomolecules, as the corresponding values of maximal excitation (Ex) and emission (Em) wavelengths and their physicochemical features and biological applications. In addition to the coumarins presented in Table 3, new sulfonyl chloride coumarins have been developed, with high potential as fluorescent probes [100,101].…”

Section: Fluorescent Coumarin Sulfonyl Chloridesmentioning

confidence: 99%

Coumarins as Fluorescent Labels of Biomolecules

Pereira¹,

Martins²,

Caldeira³

2020

Phytochemicals in Human Health

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Important areas such as environmental sciences, medicine, pharmacy, and cellular biology are dependent on very sensitive analytical techniques. One of the most common methodologies used for their bioanalytical purposes is the fluorescent labelling. The synthesis of new fluorophores and the great development of fluorescent-labelling techniques combined with the enormous technological advances in the field of fluorescence microscopy allowed to deepen the structural knowledge of biomolecules. This new organic fluorophores form covalent bonds with the sample to be analyzed, producing stable bioconjugates that show fluorescence in a wide range of wavelengths, depending on the label used. Coumarin derivatives represent one of the most important chemical classes of organic fluorescent materials being one of the most extensively investigated and commercially significant groups of organic fluorescent materials. In this chapter, it is reviewed the use of fluorescent coumarin derivatives and their application to labelling biomolecules. These fluorescent labels allow researchers to study, and understand, biomolecular assemblies that exhibit complex sensitivity and selectivity. Reactive fluorescent coumarin derivatives are actually widely used in labelling biomolecules as peptides, proteins, oligonucleotides, nucleic acids, and carbohydrates, among other biological molecules.

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An Improved Synthesis of 4-Chlorocoumarin-3-sulfonyl Chloride and Its Reactions with Different Bidentate Nucleophiles to Give Pyrido[1',2':2,3]- and Thiazino[3',2':2,3]-1,2,4-Thiadiazino[6,5-c]Benzopyran-6-one 7,7-Dioxides

Cited by 14 publications

References 24 publications

Potential antiproliferative effect of isoxazolo- and thiazolo coumarin derivatives on breast cancer mediated bone and lung metastases

Potential antiproliferative effect of isoxazolo- and thiazolo coumarin derivatives on breast cancer mediated bone and lung metastases

Recent Progress in Synthesis, POM Analyses and SAR of Coumarin-Hybrids as Potential Anti-HIV Agents—A Mini Review

Coumarins as Fluorescent Labels of Biomolecules

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