Reductive domino reaction to access chromeno[2,3-c]isoquinoline-5-amines with antiproliferative activities against human tumor cells.

Autor: Yue X; Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, Moscow, Russia., Festa AA; Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, Moscow, Russia., Storozhenko OA; Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, Moscow, Russia., Varlamov AV; Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, Moscow, Russia., Subramani K; Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, Moscow, Russia., Boccarelli A; Department of Biomedical Sciences and Human Oncology, University of Bari Aldo Moro, Piazza Giulio Cesare 11, 70124 Bari, Italy., Purgatorio R; Department of Pharmacy-Drug Sciences, University of Bari Aldo Moro, Via E. Orabona 4, 70125 Bari, Italy., Altomare CD; Department of Pharmacy-Drug Sciences, University of Bari Aldo Moro, Via E. Orabona 4, 70125 Bari, Italy., Voskressensky LG; Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st., 6, Moscow, Russia.
Jazyk: angličtina
Zdroj: Bioorganic chemistry [Bioorg Chem] 2020 Nov; Vol. 104, pp. 104169. Date of Electronic Publication: 2020 Aug 28.
DOI: 10.1016/j.bioorg.2020.104169
Abstrakt: An interaction of homophthalonitrile with salicylaldehydes proceeds as a novel domino reaction and results in the formation of nineteen 12H-chromeno[2,3-c]isoquinoline-5-amine derivatives. Four new bonds and two cycles are forged in a single synthetic operation, employing cheap and eco-friendly ammonium formate, acting both as a catalyst and a reducing agent. The in vitro cytotoxicity tests revealed antiproliferative activities against five human tumor cell lines, including the cisplatin-resistant ovarian carcinoma one (A2780cp8), with inhibitory potency data (IC 50 ) in the low micromolar range in most cases. Molecular docking calculations and fluorescence quenching studies revealed possible binding properties with DNA of the active compounds.
(Copyright © 2020 Elsevier Inc. All rights reserved.)
Databáze: MEDLINE
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