Fluorescent 2,7-Dialkylamino-[1,8]-Naphthyridines: Preparation and Spectroscopic Properties

Abstract

Substitution of 4-methyl-[1,8]-naphthyridine in 2 and 7 position by alkylamines leads to highly fluorescent compounds. The arrangement of hydrogen donor and acceptor groups of these naphthyridines allows interactions with guanine and guanine cytosine base pairs. The described synthesis offers easy access to these small and stable fluorescent probes.

7-Chloro-2,4-dimethyl-1,8-naphthyridin-1-ium nitrate

“…They can act as monodinucleating ligands (Gavrilova & Bosnich, 2004) for the preparation of multinuclear complexes, as molecular recognition receptors for urea, carboxylic acids and guanine (Goswami & Mukherjee, 1997;Nakatani et al, 2000), as medicines (Stuk et al, 2003;Ferrarini et al, 2004), and as antimycobacterial and antimicrobial agents (Badawneh et al, 2002;Badawneh et al, 2003). Recently, 1,8-naphthyridine derivatives have been reported to be excellent fluorescent markers of nucleic acids (Hoock et al, 1999) and probe molecules (Nakatani et al, 2001). We report here the structure of the title compound, (I).…”

7-[4-(5,7-Dimethyl-1,8-naphthyridin-2-yloxy)phenoxy]-2,4-dimethyl-1,8-naphthyridine methanol disolvate

“…For related literature, see: Ferrarini et al (2004); Goswami & Mukherjee (1997); Hoock et al (1999); Jin, Liu & Chen (2007); Jin, Chen & Wang (2007); Nabanita et al (2006); Nakatani et al (2000); Nakataniz et al (2001); Newkome et al (1981); Stuk et al (2003); Gavrilova & Bosnich (2004).…”

Synthesis of benzopyran[2,3‐b]quinolinone derivatives

“…They have been widely used in the medical and molecular biology [6]. Nitrogen-containing V C 2010 HeteroCorporation heterocyclic compounds have shown a strong trend of development and broad application prospects in the fields of sterilization, anti-malaria, and anti-malignant tumor [7].…”

“…The intermediate enamines 3 were obtained by condensation reaction of compounds 2 with 5-substituted-1,3-cyclohexanedione using p-toluenesulfonic acid as catalyst in toluene. 4,7,8,9,quinoline-1,10-dione derivatives 4 were synthesized by cyclization of the intermediate enamines 3 in the presence of K 2 CO 3 and Cu 2 Cl 2 [9,10]. Meanwhile, these series of novel compounds 4 could also be obtained via a one-step reaction by 4-aryl-4H-benzopyran 2 with 5-substituted-1,3-cyclohexanedione, using p-toluenesulfonic acid as catalyst in toluene.…”

“…3,4,7,8,9,10,quinoline-1-one derivatives have been synthesized by 4-aryl-4H-chromenes and cyclohexanone using AlCl 3 as catalyst in 1,2-dicholonethane [2]. Pyrano [2,3-b]pyridines were achieved by the Friedlander reaction of 2-amino-3-cyano-4H-pyrans with cyclopentanone/cyclohexanone using SnCl 2 Á2H 2 O under solvent-free condition [8].…”