239-13-4Relevant academic research and scientific papers
Mapping the reactivity of the quinoline ring-system – Synthesis of the tetracyclic ring-system of isocryptolepine and regioisomers
H?heim, Katja S.,Urdal Helgeland, Ida T.,Lindb?ck, Emil,Sydnes, Magne O.
, p. 2949 - 2957 (2019/04/25)
Bromoquinolines (2-bromoquinoline – 8-bromoquinoline and 5-bromo-3-methoxyquinoline) and 2-aminophenylboronic acid hydrochloride were subjected to Suzuki-Miyaura cross-coupling conditions resulting in formation of the desired biaryl systems in good yields. The resulting biaryls were then subjected to palladium catalyzed C–H activation/C–N bond formation utilizing PdCl2(dppf). The reactions revealed large differences in reactivity depending on the attachment point for the 2-aminophenyl group on the quinoline. The variation in the reactivity was rationalized based on the electron distribution around the quinoline ring-system.
Synthesis of 11H-Pyridocarbazoles and Derivatives. Comparison of Their DNA Binding and Antitumor Activity with THose of 6H- and 7H-Pyridocarbazoles
Lescot, Elie,Muzard, Gabriel,Markovits, Judith,Belleney, Joeel,Roques, Bernard P.,et al.
, p. 1731 - 1737 (2007/10/02)
The 8-methoxy- and 8-hydroxy-11H-pyrido-, --, --, and carbazoles were synthetized as potential DNA intercalating antitumor drugs.The structure of these compounds was confirmed by 1H NMR study including NOE experiments.The DNA binding properties of substituted and unsubstituted (8-H) heterocycles were determined by using their hydrochlorides or methiodides.These derivatives are able to bind to DNA with on affinity varying from 2.0 * 104 to 1.0 * 106 M-1, but most of them are unable to intercalate in contrast with the behavior of 6H- and 7H-pyridocarbazole analogues.The cytotoxicity of 11H-pyridocarbazoles, measured on L1210 cells in vitro, is much lower than those of 6H- and 7H-pyridocarbazole analogues.
