66471-26-9Relevant academic research and scientific papers
Dearomative Photocatalytic Construction of Bridged 1,3-Diazepanes
Dixon, Darren J.,Duarte, Fernanda,Leitch, Jamie A.,Rogova, Tatiana
supporting information, p. 4121 - 4130 (2020/02/05)
The construction of diverse sp3-rich skeletal ring systems is of importance to drug discovery programmes and natural product synthesis. Herein, we report the photocatalytic construction of 2,7-diazabicyclo[3.2.1]octanes (bridged 1,3-diazepanes) via a reductive diversion of the Minisci reaction. The fused tricyclic product is proposed to form via radical addition to the C4 position of 4-substituted quinoline substrates, with subsequent Hantzsch ester-promoted reduction to a dihydropyridine intermediate which undergoes in situ two-electron ring closure to form the bridged diazepane architecture. A wide scope of N-arylimine and quinoline derivatives was demonstrated and good efficiency was observed in the construction of sterically congested all-carbon quaternary centers. Computational and experimental mechanistic studies provided insights into the reaction mechanism and observed regioselectivity/diastereoselectivity.
Synthesis and study of nucleic acids interactions of novel monomethine cyanine dyes
Kaloyanova, Stefka,Crnolatac, Ivo,Lesev, Nedyalko,Piantanida, Ivo,Deligeorgiev, Todor
scheme or table, p. 1184 - 1191 (2012/03/27)
Six asymmetric monomethine cyanine dyes have been synthesized and their spectral characteristics and interaction with double stranded (ds)DNA have been investigated for their prospective use as fluorescent markers in molecular biology. Therefore, the non-covalent binding of the compounds with dsDNA was explored. Apart from the fluorescence spectroscopy, the study includes UV/Vis spectrophotometry and circular dichroism spectroscopy, as well as the thermal melting experiments. Although the compounds show relatively low binding affinity toward dsDNA and do not have intrinsic fluorescence, in the presence of dsDNA they exhibited considerable enhancement in fluorescence intensity. Therefore the studied dyes show interesting platform for future modifications directed toward more sequence selective derivatives. The compound with the highest affinity toward dsDNA showed interesting anti-proliferative potential and specificity.
Synthesis and fluorescence characteristics of novel asymmetric cyanine dyes for DNA detection
Kaloyanova, Stefka,Trusova, Valeriya M.,Gorbenko, Galyna P.,Deligeorgiev, Todor
scheme or table, p. 147 - 156 (2011/10/08)
Sixteen new asymmetric monomethine cyanine dyes have been synthesized and their spectral characteristics and interaction with double stranded DNA have been investigated. The dyes absorb in the region 453-519 nm and have molar absorptivities in the range 3
Organocatalytic activity of cinchona alkaloids: Which nitrogen is more nucleophilic?
Baidya, Mahiuddin,Horn, Markus,Zipse, Hendrik,Mayr, Herbert
supporting information; experimental part, p. 7157 - 7164 (2009/12/09)
(Chemical Equation Presented) The cinchona alkaloids 1a-d react selectively at the quinuclidine ring with benzyl bromide and at the quinoline ring with benzhydrylium ions (diarylcarbenium ions). The kinetics of these reactions have been determined photometrically or conductimetrically and are compared with analogous reactions of quinuclidine and quinoline derivatives. Quantum chemical calculations [MP2/6-31+G(2d,p)//B3LYP/6-31G(d)] show that the products obtained by attack at the quinuclidine ring (Nsp3) of quinine are thermodynamically more stable when small alkylating agents (primary alkyl) are used, while the products arising from attack at the quinoline ring (N sp2) are more stable for bulkier electrophiles (Ar2CH). In some cases, rate and equilibrium constants for their reactions with benzhydrylium ions could be determined. These data gave access to the Marcus intrinsic barriers, which are approximately 20 kJ mol-1 lower for attack at the Nsp3-center than at the Nsp2-center.
A new enlargement methodology for the preparation of 2H-1- and 2H-3-benzazepin-2-one derivatives
Jean-Gérard, Ludivine,Pauvert, Micka?l,Collet, Sylvain,Guingant, André,Evain, Michel
, p. 11250 - 11259 (2008/03/12)
An investigation of the one-carbon homologation of some 1-tribromomethyl-isoquinoline and 2-tribromomethyl-quinoline derivatives was conducted. Under the influence of an aqueous solution of silver nitrate in the presence of a nucleophilic species (MeOH, H
