4295-45-8Relevant academic research and scientific papers
A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities
Aksenov, Nicolai A.,Aksenov, Alexander V.,Kornienko, Alexander,De Carvalho, Annelise,Mathieu, Véronique,Aksenov, Dmitrii A.,Ovcharov, Sergei N.,Griaznov, Georgii D.,Rubin, Michael
, p. 36980 - 36986 (2018/11/23)
A second generation polyphosphoric acid-mediated one-pot three-component synthesis of indoloquinoline scaffold is developed. This improved version of the process involves electrophilically activated nitroalkanes for the installation of strategic C-C and C-N bonds and ring C assembly. This modification allows the elimination of unnecessary solvent change operations and all steps are carried out in a true, uninterrupted one-pot manner. A further improvement involves the possibility to install an ortho-amino group in situ. A synthetic application of this method is showcased by the concise synthesis of an isocryptolepine alkaloid and its synthetic analogs with potent anticancer activities.
One-Pot, Three-Component Assembly of Indoloquinolines: Total Synthesis of Isocryptolepine
Aksenov, Alexander V.,Aksenov, Dmitrii A.,Orazova, Naila A.,Aksenov, Nicolai A.,Griaznov, Georgii D.,De Carvalho, Annelise,Kiss, Robert,Mathieu, Véronique,Kornienko, Alexander,Rubin, Michael
, p. 3011 - 3018 (2017/03/23)
Indolo[3,2-c]quinolones have been efficiently synthesized via an acid-mediated, one-pot, three-component condensation of arylhydrazines, o-aminoacetophenones, and triazines or nitriles. The synthetic application of this method is showcased by the concise synthesis of isocryptolepine alkaloid and a series of its synthetic analogues with demonstrated cancer cell antiproliferative activities.
From biomass to medicines. A simple synthesis of indolo[3,2-c]quinolines, antimalarial alkaloid isocryptolepine, and its derivatives
Uchuskin, Maxim G.,Pilipenko, Arkady S.,Serdyuk, Olga V.,Trushkov, Igor V.,Butin, Alexander V.
supporting information; experimental part, p. 7262 - 7265 (2012/09/22)
Indolo[3,2-c]quinolines are pharmacologically attractive class of heterocyclic compounds. The method of their synthesis, based on transformation of furfural, which is a large-scale product of treatment of biomass including agricultural and forestry wastes, has been developed. This method was utilized for the total synthesis of antimalarial alkaloid isocryptolepine and its derivatives.
Design of antineoplastic agents based on the '2-phenylnaphthalene-type' structural pattern - Synthesis and biological activity studies of 11H-indolo[3.2-c]quinoline derivatives
He, Ling,Chang, He-Xi,Chou, Ting-Chao,Savaraj, Niramol,Cheng
, p. 101 - 107 (2007/10/03)
Designed as a new group of planar molecule containing the proposed 2-phenylnaphthalene-type structure, a number of 11H-indolo[3.2-c]quinoline derivatives were synthesized and evaluated biologically. Several compounds were found to possess cytotoxic activity against the growth of human promyelocytic leukemia cells (HL-60), against the small cell lung cancer (SCLC), and showed good response in the National Cancer Institute preclinical antitumor drug discovery 60-cell line panel.
Structure-activity relationships of antimalarial indoloquinolines
Werbel, L. M.,Kesten, S. J.,Turner, W. R.
, p. 837 - 852 (2007/10/02)
Structure-activity relationships have been ascertained and chemical metodology developed for a series of antimalarial 3-chloroindoloquinoline-5-oxides.The basic side chain as well as the ring N-oxide are critical for antimalarial activity as is a bromine or chlorine in position 3.Substitution at positions 7,8,9,10 in not essential, although the most potent analog in our studies was the 8-nitro compound 4vv. indoloquinolines / antimalarial agents
