Multinuclear NMR spectroscopy, photophysical, electrochemical and DNA-binding properties of fluorinated 1,8-naphthyridine-based boron heterocycles

Bonacorso, Hélio G.; Calheiro, Tainara P.; Iglesias, Bernardo A.; Silveira, Carolina Hahn da; Júnior, Eufrânio N. da Silva; Ketzer, Alex; Bublitz, Fabrício; Zanatta, Nilo; Martins, Marcos A. P.

doi:10.1016/j.jfluchem.2017.11.006

Cited by 15 publications

(4 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…shift in some cases was also observed, indicating a weak or nonelectrostatic interaction observed between the cited compounds and CT-DNA (Table 4). The transition change of the derivatives may be a result of the interaction of the BF 2 moiety with the nucleobase residues of the DNA (Figure 3), which are possible via hydrophobic forces, as previously in the literature (Bonacorso et al, 2018b).…”

Section: Solventmentioning

confidence: 56%

Novel Alkyl(aryl)-Substituted 2,2-Difluoro-6-(trichloromethyl)-2H-1,3,2-oxazaborinin-3-ium-2-uides: Synthesis, Antimicrobial Activity, and CT-DNA Binding Evaluations

et al. 2020

Self Cite

View full text Add to dashboard Cite

The synthesis, antimicrobial activity evaluations, biomolecule-binding properties (DNA), and absorption and emission properties of a new series of (Z)-1,1,1-trichloro-4-alkyl(aryl) amino-4-arylbut-3-en-2-ones (4, 5) and 2,2-difluoro-3-alkyl(aryl)amino-4-aryl-6-(trichloromethyl)-2H-1,3,2-oxazaborinin-3-ium-2-uides (6, 7) in which 3(4)-alkyl(aryl) = H, Me, iso-propyl, n-butyl, C 6 H 5 , 4-CH 3 C 6 H 4 , 4-CH 3 OC 6 H 4 , 4-NO 2 C 6 H 4 , 4-FC 6 H 4 , 4-BrC 6 H 4 , 2-naphthyl, is reported. A series of b-enaminoketones (4, 5) is synthesized from the O,N-exchange reaction of some amines (3) with (Z)-1,1,1-trichloro-4-methoxy-4-arylbut-3-en-2-ones (1, 2) at 61-90% yields. Subsequently, reactions of the resulting benaminoketones with an appropriate source of boron (BF 3 .OEt 2) gave the corresponding oxazaborinine derivatives (6, 7) at 50-91% yields. UV-Vis and emission properties of biomolecule-binding properties for the DNA of these new BF 2-b-enamino containing CCl 3 units were also evaluated. Some compounds from the present series also exhibited potent antimicrobial effects on various pathogenic microorganisms at concentrations below those that showed cytotoxic effects. Compounds 4d, 4e, 6e, and 6f showed the best results and are very significant against P. zopfii, which causes diseases in humans and animals.

show abstract

Section: Solventmentioning

confidence: 56%

Novel Alkyl(aryl)-Substituted 2,2-Difluoro-6-(trichloromethyl)-2H-1,3,2-oxazaborinin-3-ium-2-uides: Synthesis, Antimicrobial Activity, and CT-DNA Binding Evaluations

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

“…The type of aryl group, spacers and mode of coordination had influence on the photophysical properties of the resultant products. 135–169 The Lu group 142,149 synthesized N,O-chelated BF 2 compounds 138–142 (Fig. 17).…”

Section: No-chelate B–n Coordinated Compoundsmentioning

confidence: 99%

Recent advances in the synthesis of luminescent tetra-coordinated boron compounds

2022

View full text Add to dashboard Cite

show abstract

“… [124] The amino moiety was reacted with acyl chlorides to furnish amides 130 , at 65–95 % yields (Et 3 N, refluxing CH 2 Cl 2 , 16 h). Lastly, 130 was reacted with boron trifluoride etherate, which furnished BF 2 ‐containing heterocycles 131 at 50–65 % yields (CHCl 3 , Et 3 N, 18 h) [125,126] . Compounds 131 showed low inhibition of the AChE enzyme (8–26 %) and activation of tyrosinase activity (1–14 %).…”

Section: Synthesis Of Other Heterocyclic Systems With Promising Biological Activitymentioning

confidence: 99%

Haloacetylated Enol Ethers: a Way Out for the Regioselective Synthesis of Biologically Active Heterocycles

2021

Self Cite

View full text Add to dashboard Cite

This review describes advances in the synthesis of heterocyclic scaffolds (associated with their biological activity), using haloacetylated enol ethers as precursors. The wide variety of heterocycles that can be prepared using these precursors, together with the high regioselectivity they usually provide, in [3+2] and [3+3] cyclocondensation reactions, make these starting materials powerful tools. The biological evaluation is also highlighted, given that several analogues of commercially available drugs can be easily accessed.

show abstract

Multinuclear NMR spectroscopy, photophysical, electrochemical and DNA-binding properties of fluorinated 1,8-naphthyridine-based boron heterocycles

Cited by 15 publications

References 17 publications

Novel Alkyl(aryl)-Substituted 2,2-Difluoro-6-(trichloromethyl)-2H-1,3,2-oxazaborinin-3-ium-2-uides: Synthesis, Antimicrobial Activity, and CT-DNA Binding Evaluations

Novel Alkyl(aryl)-Substituted 2,2-Difluoro-6-(trichloromethyl)-2H-1,3,2-oxazaborinin-3-ium-2-uides: Synthesis, Antimicrobial Activity, and CT-DNA Binding Evaluations

Recent advances in the synthesis of luminescent tetra-coordinated boron compounds

Haloacetylated Enol Ethers: a Way Out for the Regioselective Synthesis of Biologically Active Heterocycles

Contact Info

Product

Resources

About