title: Synthesis and antiproliferative activity of aromatic and aliphatic bis[aminomethylidene(bisphosphonic)] acids.
abstract: A series of aromatic and aliphatic bis[aminomethylidene(bisphosphonic)] acids was synthesized in the reaction of triethylphosphite with isonitriles followed by hydrolysis or dealkylation. The in vitro anti-proliferative effect of all synthesized tetraphosphonic acids against MCF-7 breast cancer cells, J774E macrophages and HL-60 promyelocytic leukemia cells was determined. Three aromatic derivatives (5a, 5f and 5j) showed a similar or higher anti-proliferative activity than zoledronic acid.
authors.affiliation: Wrocław University of Technology, Department of Organic Chemistry, Wybrzeże Wyspiańskiego 27, Wrocław 50-370, Poland. Electronic address: waldemar.goldeman@pwr.wroc.pl.
authors.forename: Waldemar
authors.initials: W
authors.lastname: Goldeman
authors.affiliation: Polish Academy of Sciences, Institute of Immunology and Experimental Therapy, Rudolfa Weigla 12, Wrocław 53-114, Poland.
authors.forename: Anna
authors.initials: A
authors.lastname: Nasulewicz-Goldeman
mesh_terms: D015057:1-Naphthylamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004164:Diphosphonates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D061986:MCF-7 Cells; D008264:Macrophages / Q000187:drug effects*; D015394:Molecular Structure; D010655:Phenylenediamines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000814:Aniline Compounds; D000970:Antineoplastic Agents; D004164:Diphosphonates; D010655:Phenylenediamines; C000595744:benzene-1,4-bis(aminomethylidene(bisphosphonic)) acid; C000595746:naphthalene-1,5-bis(aminomethylidene(bisphosphonic)) acid; C000595745:sulfonyldiphenyl-4,4'-bis(aminomethylidene(bisphosphonic)) acid; D015057:1-Naphthylamine
keywords: Anti-proliferative activity; Bisphosphonate; Bisphosphonic acid; Isocyanide; Isonitrile; Osteoclasts; Tetraphosphonate; Tumor cells