66571-30-0Relevant academic research and scientific papers
Synthesis and DNA binding properties of γ-carbolinium derivatives and benzologues
Molina,Vaquero,Garcia-Navio,Alvarez-Builla,De Pascual-Teresa,Gago,Rodrigo,Ballesteros
, p. 5587 - 5599 (2007/10/03)
The 5H-pyrido[4,3-b]indole, 11H-indolo[3,2-c]quinoline, 5H-benzo[f]pyrido[4,3-b]indole, and 13H-benz[5,6]indolo[3,2-c]quinoline heteroaromatic nuclei have been synthesized by the Graebe-Ullmann method by classical heating or under microwave irradiation. These tri-, tetra-, and pentacyclic compounds were transformed into the corresponding cationic derivatives by N-alkylation, and the DNA-binding properties of the resulting cationic systems were examined using UV-vis spectroscopy, viscometric determinations, and molecular modeling techniques. The tetracyclic cations were transformed into bis-salts by means of a diethyl bispiperidine rigid chain and a more flexible polyamide linker, but the low solubility of these bis-salts made the study of their bisintercalating properties difficult.
Fluorescence Studies with Tryptophan Analogues: Excited State Interactions Involving the Side Chain Amino Group
Eftink, Maurice R.,Jia, Yiwei,Hu, Dana,Ghiron, Camillo, A.
, p. 5713 - 5723 (2007/10/02)
The fluorescence of a large set of tryptophan analogues, including several that are conformationally constrained, was studied.The constrained analogues include tetrahydrocarboline-3-carboxylic acid and 3-amino-3-carboxytetrahydrocarbazole.Steady state and time-resolved fluorescence measurements were made as a function of pH.The fluorescence quantum yields of the constrained analogues are higher than those for the unconstrained counterparts.The emission intensity of the constrained analogues, as well as 4-methyltryptophan, decreases with deprotonation of the side chain α-ammonium groups; this is in contrast to the increase in fluorescence of tryptophan with deprotonation of this group.These results are consistent with the existence of excited state proton transfer to carbon 4 of the indole ring as a quenching mechanism, which is sterically prohibited in the constrained analogues and 4-methyltryptophan.From quantum yield and lifetime data (most decays are nonexponential), the effective rate constant for nonradiative depopulation of the excited state was calculated.For tryptophan analogues having two side chain functional groups, there is a synergistic effect; the presence of two side chain groups causes more quenching than expected from the sum of the individual contributions.For analogues having an α-ammonium group, this synergism appears to be correlated with an induced change in the pKa of this group.Deprotonation of this α-ammonium group also caused a red shift in the emission of these compounds; this appears to be due to electrostatic repulsion between the α-NH3+ group and the excited indole dipole.
One-pot Graebe-Ullmann synthesis of γ-carbolines under microwave irradiation
Molina, Andres,Vaquero, Juan J.,Garcia-Navio, Jose L.,Alvarez-Builla, Julio
, p. 2673 - 2676 (2007/10/02)
One-pot efficient and simple synthesis of γ-carboline derivatives by the Graebe-Ullmann method was conducted in a commercial microwave oven in a few minutes at a low energy level and using erlenmeyer as adequate reaction vessels. Yields are similar to those obtained by conventional heating.
Synthetic Applications of N-N Linked Heterocycles. Part 9. Preparation of α-(4-Pyridyl)nitroalkanes and N-(4-Pyridyl)azoles by Regiospecific Attack of Nitroalkyl and Azolyl Anions on N-(2,6-Dimethyl-4-oxopyridin-1-yl)pyridinium Salts
Katritzky, Alan R.,Keay, James G.,Rogers, David N.,Sammes, Michael P.,Leung, Christopher W.F.
, p. 588 - 592 (2007/10/02)
Sodium salts of nitroalkanes and of azoles react with N-(2,6-dimethyl-4-oxopyridin-1-yl)pyridinium salts (1) - (3) to give regiospecifically 1,4-dihydropyridines (12) - (14), (15), and (16) in high yields.Photolysis of the dihydropyridines gives α-(4-pyri
