Microwave-assisted synthesis and photophysical studies of novel fluorescent N-acylhydrazone and semicarbazone-7-OH-coumarin dyes

Pereira, Thiago Moreira; Vitório, Felipe; Amaral, Ronaldo C.; Zanoni, Kassio P. S.; Iha, Neyde Yukie Murakami; Kümmerle, Arthur Eugen

doi:10.1039/c6nj01532h

Cited by 37 publications

(16 citation statements)

References 42 publications

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“…The electronic spectra of the compounds (SI, Figures S8 and S9) displayed intense spin–allowed π → π* absorption features around 450 nm in phosphate buffer, with ε on the order of 10 4 L mol –1 cm –1 . Coumarin derivatives containing the 7–N(Et) 2 and 7‐OH groups displayed absorptions around 350–430 nm, attributed to π → π* . Previous studies of coumarin–N–acylhydrazone hybrids and their corresponding Co III complexes showed the same type of transition in the region of 405–470 nm in phosphate buffer.…”

Section: Resultsmentioning

confidence: 68%

Redox‐Activated Drug Delivery Properties and Cytotoxicity of Cobalt Complexes Based on a Fluorescent Coumarin‐β‐Keto Ester Hybrid

et al. 2019

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The search for new Co III -based drug delivery systems has attracted considerable attention in recent years. In this work, two cobalt complexes with general formula [Co(L)Am](ClO 4 ) n were synthesized, in which L -= (ethyl-3-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-3-oxopropanoate), a coumarin--keto ester ligand, and Am is the auxiliary amine TPA (tris-(2-pyridylmethyl)amine) or Py 2 en (2-pyridylmethyl)-1,2diamine). Complexation reactions yielded [Co II (L)TPA]ClO 4 (1) and [Co III (L)Py 2 en](ClO 4 ) 2 (2), and the Co III complex (2) was investigated as a potential hypoxia-activated prodrug prototype.[a]

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Section: Resultsmentioning

confidence: 68%

Redox‐Activated Drug Delivery Properties and Cytotoxicity of Cobalt Complexes Based on a Fluorescent Coumarin‐β‐Keto Ester Hybrid

et al. 2019

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“…Electronic spectral data for Hachbt and its complexes ( 1 – 5 ) in DMSO are listed in the Experimental section and are shown in Figure S3. The ligand exhibits three bands at 289, 365 and 546 nm due to intraligand π‐π* and n‐π* transitions 64, 65 . The UV–Vis spectra of the Zn (II) and Ag (1) complexes (d 10 configuration) show similar behavior to that of the ligand with slight red shifts to the higher wavelengths (~ 5 nm) owing to coordination to the metal ion 52, 66 .…”

Section: Resultsmentioning

confidence: 97%

Novel metal complexes of 3‐acetylcoumarin‐2‐hydrazinobenzothiazole Schiff base: Design, structural characterizations, DNA binding, DFT calculations, molecular docking and biological studies

Elsayed

El‐Gharabawy

Butler

et al. 2020

Applied Organom Chemis

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Five new Cu (II), Zn (II), Pd (II), Ru (III) and Ag(I) complexes, derived from the 3‐acetylcoumarin‐2‐hydrazinobenzothiazole Schiff base (Hachbt), have been synthesized and characterized. The structures were established with the aid of elemental analyses (C, H, N), FT‐IR, 1H‐NMR, ESR, UV–visible and ESI‐mass spectra. The complexes were also investigated by magnetic susceptibility, thermal gravimetric analysis (TG‐DTA) and cyclic voltammetry measurements. The results suggest that the Schiff base ligand behaves in two different ways: neutral mono/bidentate or mono‐negative bi/tridentate. The calf thymus DNA (CT DNA) binding affinities of Hachbt and its complexes have been examined by UV–visible spectroscopy. The antifungal activity of the compounds was also screened against two fungal species of wood‐decay basidiomycetes using the agar dilution method. Different complexes caused a reduction in the fungal colony diameters at a media concentration of 100 μg/ml. The best antifungal activity was observed for the Pd (II) and Ag(I) complexes with a 60% and 79% reduction, respectively. The effect of the complexes on the ability of the same fungi to decolorize poly‐R dye on agar plates was also tested. All of the complexes showed an enhanced effect on the decolorization ability and the Cu (II) and Ru (III) complexes exhibited the strongest effect at a media concentration of 5 μg/ml. Theoretical studies were performed for all the complexes using the DFT/B3LYP/6–31 + g(d) basis set for calculations on the ligand atoms and LAN2DZ for the Pd (II) complex. The optimized geometries were found to be in a good agreement with the proposed structures. The molecular docking calculations show that the binding affinity of the Pd (II) complex is −309.170‐309.2 kcal/mol, which suggests complexation with the DNA minor groove.

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“…In the mid-nineteenth century, the research and development of coumarin-based compounds and hybrid structures began via the famous Perkin condensation reaction between acetic anhydride and salicylaldehyde. The different synthetic classical techniques, such as Knoevenagel, Perkin and Pechmann reactions, are applied to achieve simple coumarins [ 5 , 6 , 7 ]. The rapid developments in the synthetic chemistry of coumarins have been made, due to their wide therapeutic potential as medicinal drugs.…”

Section: Introductionmentioning

confidence: 99%

An Update on Synthesis of Coumarin Sulfonamides as Enzyme Inhibitors and Anticancer Agents

et al. 2022

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Coumarin is an important six-membered aromatic heterocyclic pharmacophore, widely distributed in natural products and synthetic molecules. The versatile and unique features of coumarin nucleus, in combination with privileged sulfonamide moiety, have enhanced the broad spectrum of biological activities. The research and development of coumarin, sulfonamide-based pharmacology, and medicinal chemistry have become active topics, and attracted the attention of medicinal chemists, pharmacists, and synthetic chemists. Coumarin sulfonamide compounds and analogs as clinical drugs have been used to cure various diseases with high therapeutic potency, which have shown their enormous development value. The diversified and wide array of biological activities such as anticancer, antibacterial, anti-fungal, antioxidant and anti-viral, etc. were displayed by diversified coumarin sulfonamides. The present systematic and comprehensive review in the current developments of synthesis and the medicinal chemistry of coumarin sulfonamide-based scaffolds give a whole range of therapeutics, especially in the field of oncology and carbonic anhydrase inhibitors. In the present review, various synthetic approaches, strategies, and methodologies involving effect of catalysts, the change of substrates, and the employment of various synthetic reaction conditions to obtain high yields is cited.

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Microwave-assisted synthesis and photophysical studies of novel fluorescent N-acylhydrazone and semicarbazone-7-OH-coumarin dyes

Abstract: Emissive 7-OH-coumarins were synthesized by a microwave-assisted protocol and spectral changes were induced after conformational changes in low polarity media.

Cited by 37 publications

References 42 publications

Redox‐Activated Drug Delivery Properties and Cytotoxicity of Cobalt Complexes Based on a Fluorescent Coumarin‐β‐Keto Ester Hybrid

Redox‐Activated Drug Delivery Properties and Cytotoxicity of Cobalt Complexes Based on a Fluorescent Coumarin‐β‐Keto Ester Hybrid

Novel metal complexes of 3‐acetylcoumarin‐2‐hydrazinobenzothiazole Schiff base: Design, structural characterizations, DNA binding, DFT calculations, molecular docking and biological studies

An Update on Synthesis of Coumarin Sulfonamides as Enzyme Inhibitors and Anticancer Agents

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