title: One-pot microwave assisted synthesis of new 2-alkoxycarbonylmethylene-4-oxo-1,5-benzo-, naphtho-, and pyridodiazepines and assessment of their cytogenetic activity.
abstract: 1,5-Benzo-, naphtho-, and pyridodiazepines 3 have been synthesized in excellent yields in one-step from the reaction of o-phenylenediamines with acetonedicarboxylates through microwave assisted acid catalysis. In order to ascertain their cytogenetic activity in vitro at doses equivalent to the per os doses of common 1,4-benzodiazepine drugs, Sister Chromatid Exchanges (SCEs) were employed, and for the determination of cytostaticity the Proliferation Rate Index (PRI) on lymphocytes of human whole blood cultures was estimated. It was found that benzodiazepines 3a, 3c, and 3e exhibit significant cytoprotection, but mild cytostatic effect (a statistically significant reduction of SCEs and a confined decrease of PRI values at similar concentrations). The most active compound was found to be 3e.
authors.affiliation: Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece.
authors.forename: Nicolaos
authors.initials: N
authors.lastname: Eleftheriadis
authors.forename: Constantinos G
authors.initials: CG
authors.lastname: Neochoritis
authors.forename: Constantinos A
authors.initials: CA
authors.lastname: Tsoleridis
authors.forename: Julia
authors.initials: J
authors.lastname: Stephanidou-Stephanatou
authors.forename: Zafiroula
authors.initials: Z
authors.lastname: Iakovidou-Kritsi
mesh_terms: D001381:Azepines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002478:Cells, Cultured; D004305:Dose-Response Relationship, Drug; D006801:Humans; D008214:Lymphocytes / Q000166:cytology / Q000187:drug effects*; D008872:Microwaves; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D012854:Sister Chromatid Exchange / Q000187:drug effects* / Q000235:genetics; D013329:Structure-Activity Relationship
chemical_list: D001381:Azepines; D011725:Pyridines
keywords: 1,5-Benzodiazepines; Cytogenetic activity; Microwave irradiation; Proliferation Rate Index; Sister Chromatid Exchanges