Synthesis and fluorescence study of 6,7-diaminocoumarin and its imidazolo derivatives

Reddy, T. Sheshashena; Reddy, A. Ramachandra

doi:10.1016/j.dyepig.2012.08.021

Cited by 20 publications

(10 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Section: Resultsmentioning

confidence: 99%

“…Compound 7 was hydrolysed under standard acidic conditions to afford 6-nitro-7-amino-4-methylcoumarin 8 (80 % yield), which was reduced using tin/HCl as reported to give the key intermediate 6,7-diamino-4-methylcoumarin 9, in 36 % yield (Scheme 1). 21 Transporters 1, 2, and 4 were prepared by nucleophilic addition of the 6,7-diamino-4-methylcoumarin 9 with the corresponding aryl isocyanate in dichloromethane overnight at 45 °C under an inert atmosphere. Interestingly, attempts to prepare transporter 3 using the same procedure failed.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

A potent fluorescent transmembrane HCl transporter perturbs cellular pH and promotes cancer cell death

Farès

McNaughton

et al. 2023

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

A potent fluorescent transmembrane HCl transporter perturbs cellular pH and promotes cancer cell death

Farès

McNaughton

et al. 2023

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

“…The literature provides some information about the fluorescence mechanisms of DMACA alone, in the absence of PAs (Bangal et al, 2001). DMACA and its derivatives have also been used to create fluorescence probes by reacting with various compounds, which can form a double twistable ethylene structure with intramolecular charge transfer capabilities and hence, emit fluorescence in the red to infrared spectra upon photoexcitation (Chen et al, 2021;Gao et al, 2022;Sheshashena Reddy and Ram Reddy, 2013). However, further studies are needed to understand the chemistry and physics of We revealed that PA-specific DMACA fluorescence lies in the red light region of the spectrum, which we confirmed by in vitro determination using commercial and isolated PAs commonly present in plants and by in situ determination of hybrid aspen roots known to be rich in PAs (Dixon et al, 2005).…”

Section: Discussionmentioning

confidence: 99%

Fluorogenic properties of 4-dimethylaminocinnamaldehyde (DMACA) enable high resolution imaging of cell-wall-bound proanthocyanidins in plant root tissues

et al. 2023

View full text Add to dashboard Cite

Proanthocyanidins (PAs) are polymeric phenolic compounds found in plants and used in many industrial applications. Despite strong evidence of herbivore and pathogen resistance-related properties of PAs, their in planta function is not fully understood. Determining the location and dynamics of PAs in plant tissues and cellular compartments is crucial to understand their mode of action. Such an approach requires microscopic localization with fluorescent dyes that specifically bind to PAs. Such dyes have hitherto been lacking. Here, we show that 4-dimethylaminocinnamaldehyde (DMACA) can be used as a PA-specific fluorescent dye that allows localization of PAs at high resolution in cell walls and inside cells using confocal microscopy, revealing features of previously unreported wall-bound PAs. We demonstrate several novel usages of DMACA as a fluorophore by taking advantage of its double staining compatibility with other fluorescent dyes. We illustrate the use of the dye alone and its co-localization with cell wall polymers in different Populus root tissues. The easy-to-use fluorescent staining method, together with its high photostability and compatibility with other fluorogenic dyes, makes DMACA a valuable tool for uncovering the biological function of PAs at a cellular level in plant tissues. DMACA can also be used in other plant tissues than roots, however care needs to be taken when tissues contain compounds that autofluoresce in the red spectral region which can be confounded with the PA-specific DMACA signal.

show abstract

“…Subsequent alkaline hydrolysis of compound (77) yielded compound (78), which was then condensed with chloropropanone (4) to generate the pivotal intermediate (79). Leveraging the methyl substitution at C8 to prevent angular fusion, intermediate (79) underwent cyclization in an alkaline environment, leading to the formation of a linear fusion between thiophene and coumarin, thereby yielding compound (80). Finally, compound (80) underwent bromination by heating it to its boiling point in an acetic solution of hydrobromide and with the aid of an acetic anhydride, where the bromide substituent was replaced by an acetoxy moiety, resulting in the target compound (81) as depicted in Scheme 13.…”

Section: Thiopheno[g]coumarinsmentioning

confidence: 99%

Annulated Heterocyclic[g]Coumarin Composites: Synthetic Approaches and Bioactive Profiling

Mazin Zeki,

Fakri Mustafa

2024

Chemistry & Biodiversity

View full text Add to dashboard Cite

Coumarins, widely abundant natural heterocyclic compounds, are extensively employed in creating various biologically and pharmacologically potent substances. The hybridization of heterocycles presents a key opportunity to craft innovative multicyclic compounds with enhanced biological activity. Fusing different heterocyclic rings with the coumarin structure presents an intriguing method for crafting fresh hybrid compounds possessing remarkable biological effects. In the pursuit of creating heterocyclic‐fused coumarins, a wide range of annulated heterocyclic[g]coumarin composites has been introduced, displaying impressive biological potency. The influence of the linear attachment of heterocyclic rings to the coumarin structure on the biological performance of the resulting compounds has been investigated. This review centers on the synthetic methodologies, structural activity relationship investigation, and biological potentials of annulated heterocyclic[g]coumarin composites. We conducted searches across several databases, including Web of Science, Google Scholar, PubMed, and Scopus. After sieving, we ultimately identified and included 71 pertinent studies published between 2000 and the middle of 2023. This will provide valuable perspectives for medicinal chemists in the prospective design and synthesis of lead compounds with significant therapeutic effects, centered around heterocycle‐fused coumarin frameworks.

show abstract

Synthesis and fluorescence study of 6,7-diaminocoumarin and its imidazolo derivatives

Cited by 20 publications

References 44 publications

A potent fluorescent transmembrane HCl transporter perturbs cellular pH and promotes cancer cell death

A potent fluorescent transmembrane HCl transporter perturbs cellular pH and promotes cancer cell death

Fluorogenic properties of 4-dimethylaminocinnamaldehyde (DMACA) enable high resolution imaging of cell-wall-bound proanthocyanidins in plant root tissues

Annulated Heterocyclic[g]Coumarin Composites: Synthetic Approaches and Bioactive Profiling

Contact Info

Product

Resources

About