New 2-(aryl/heteroaryl)-6-(morpholin-4-yl/pyrrolidin-1-yl)-(4-trifluoromethyl)quinolines: synthesis via Buchwald–Hartwig amination, photophysics, and biomolecular binding properties

Abstract

New 6-(morpholino/pyrrolidino)quinolines displaying interesting photophysical and biomolecular binding properties achieved by Buchwald–Hartwig amination.

Hybridized 4‐Trifluoromethyl‐(1,2,3‐triazol‐1‐yl)quinoline System: Synthesis, Photophysics, Selective DNA/HSA Bio‐interactions and Molecular Docking

“…The 19 F‐NMR spectra of compounds 6 – 8 showed only one singlet with an average value of −60.78 ppm and corresponding to the CF 3 group, in which structural assignments are consistent with the spectral data described in the literature for similar compounds [25,27,30] . Figure 1 shows 1 H−, 13 C−, and 19 F NMR on average chemical shifts for compounds 6 – 8 , in which NMR data can be used to characterize all compounds of these series of compounds.…”

“…Therefore, molecular hybridization strategies based on combining quinoline and 1,2,3‐triazole heterocycles, such as bioactive pharmacophoric frameworks whose combination (fusion or conjugation) of the mentioned rings in a single hybrid molecule demonstrate enormous relevance in drug discovery given their broad coverage of pharmaceutical and therapeutic applications, including anti‐inflammatory and analgesic, [8] antimicrobial, [9,10] antifungal and antibacterial, [11–14] antitubercular, [15–18] antimalarial, [19] and antiviral [20] activities, strongly influence pharmacokinetics, drug targeting, and mechanisms of action [2,21] . Recent studies of compounds containing a conjugation of different types of aza‐heterocycles in the same molecule (e. g., quinoline and 1,2,3‐triazole) have also received considerable attention in therapeutic and anticancer applications [22–25] . The molecular binding studies of these compounds are important tool to understand the interaction mode of these compounds with different biomolecules [22,26] …”

Bromo‐Substituted Diazenyl‐pyrazolo[1,5‐a]pyrimidin‐2‐amines: Sonogashira Cross‐Coupling Reaction, Photophysical Properties, Bio‐interaction and HSA Light‐Up Sensor

“…No blue or red shifts were observed for all derivatives, indicating the non‐electrostatic interaction of the molecules and HSA (Figure 5). The increased intensity of the related transition bands could be accounted for by the interaction of the aromatic portion of the compounds, and this was likely via hydrophobic forces (van der Waals, H‐bonding, or p‐stacking) with the biomolecule [27,29] …”

“…In addition, the presence of the trifluoromethylated group (CF 3 ) in several organic compounds generates stereo‐electronic changes since this substituent has high electronegativity due to fluorine being a very electronegative atom. Given this scenario, inserting this group affects the electronic density of the heterocycles in which it is inserted, changing the electronic densities and affecting the biological and photophysical properties of the molecules [27–33] …”

“…Given this scenario, inserting this group affects the electronic density of the heterocycles in which it is inserted, changing the electronic densities and affecting the biological and photophysical properties of the molecules. [27][28][29][30][31][32][33] Thus, after synthesizing the series of diazenyl-pyrazolo[1,5a]pyrimidin-2-amine (DPPA) (1), [30] this study aimed to report the results of synthesizing a series of (E)-(alkyl/ heteroaryl)ethynyl)phenyl)diazenyl)-7-(trifluoromethyl)pyrazolo [1,5-a]pyrimidin-2-amines (2-4) using standard Sonogashira coupling reactions. Due to halogens at the 4-bromoaniline and/or 4-methoxy-4-(4-bromophenyl)-1,1,1-trifluorobut-3en-2-one of compounds 1, it was possible to promote these reactions using terminal alkynes and metal as catalysts (Scheme 1).…”