title: Efficient one-pot synthesis of 5-perfluoroalkylpyrazoles by cyclization of hydrazone dianions.
abstract: A highly selective and efficient method for the synthesis of 5-trifluoromethylated and 5-perfluoroalkylated pyrazoles has been developed which relies on the cyclization of hydrazine dianions with ethyl perfluorocarboxylates. The pyrazoles prepared were evaluated as potential inhibitors of alkaline phosphatases, namely human tissue non-specific alkaline phosphatase (h-TNAP) and tissue specific intestinal alkaline phosphatase (IAP). Most pyrazole derivatives inhibited h-IAP more markedly than h-TNAP and had minor effects on nucleotide pyrophosphatase/phosphodiesterases. Therefore, the compounds appear as potential selective inhibitors of h-IAP.
authors.affiliation: Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany. peter.langer@uni-rostock.de thanhtuandang@hotmail.com.
authors.forename: Thang Ngoc
authors.initials: TN
authors.lastname: Ngo
authors.forename: Syeda Abida
authors.initials: SA
authors.lastname: Ejaz
authors.forename: Tran Quang
authors.initials: TQ
authors.lastname: Hung
authors.forename: Tuan Thanh
authors.initials: TT
authors.lastname: Dang
authors.forename: Jamshed
authors.initials: J
authors.lastname: Iqbal
authors.forename: Joanna
authors.initials: J
authors.lastname: Lecka
authors.forename: Jean
authors.initials: J
authors.lastname: Sévigny
authors.forename: Peter
authors.initials: P
authors.lastname: Langer
mesh_terms: D016573:Agrochemicals / Q000737:chemistry; D000469:Alkaline Phosphatase / Q000037:antagonists & inhibitors / Q000378:metabolism; D000818:Animals; D000838:Anions; D019556:COS Cells; D002625:Chemistry, Organic / Q000379:methods*; D002522:Chlorocebus aethiops; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000494:pharmacology; D006801:Humans; D006835:Hydrazones / Q000737:chemistry*; D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry; D004364:Pharmaceutical Preparations / Q000737:chemistry; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry; D011755:Pyrophosphatases / Q000037:antagonists & inhibitors / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D016573:Agrochemicals; D000838:Anions; D004791:Enzyme Inhibitors; D006835:Hydrazones; D007555:Isoxazoles; D004364:Pharmaceutical Preparations; D011720:Pyrazoles; C031280:pyrazole; D000469:Alkaline Phosphatase; D011755:Pyrophosphatases; C021899:nucleotide pyrophosphatase