Synthesis of Trifluoromethylated 3-(3-Pyrazolyl)indole-N-glycosides and their Cytotoxic Activity against Human Keratinocytes (HaCaT)

The first 3-(3-pyrazolyl)indole-N-glycosides were prepared starting from indole-N-glycosides by conversion with 4-ethoxy-1,1,1-trifluorobut-3-en-2-one and following cyclization with hydrazine. The cytotoxic activity of the products against human keratinocytes (HaCaT) was studied.

[1]  M. Hein,et al.  The First N-Glycosylated Indoxylsand Their Application to the Synthesis of Indirubin-N-glycosides (Purple Sugars) , 2009 .

[2]  M. Lalk,et al.  Synthesis of 6H-indolo[2,3-b]quinoxaline-N-glycosides and their cytotoxic activity against human ceratinocytes (HaCaT). , 2008, Organic & biomolecular chemistry.

[3]  D. Fabbro,et al.  In-vitro antiproliferative activities and kinase inhibitory potencies of glycosyl-isoindigo derivatives , 2007, Anti-cancer drugs.

[4]  C. Lamberth.  Pyrazole chemistry in crop protection , 2007 .

[5]  Qingmin Wang,et al.  Synthesis and bioassay evaluation of 1-(4-substitutedideneaminooxymethyl)-phenyl-3-(2,6-difluorobenzoyl)ureas. , 2007, Bioorganic & medicinal chemistry.

[6]  M. Hein,et al.  Fluorinated acyclo-C-nucleoside analogues from glycals in two steps. , 2006, Carbohydrate research.

[7]  W. Holzer,et al.  Synthesis of pyrazole-based hybrid molecules: search for potent multidrug resistance modulators. , 2006, Bioorganic & medicinal chemistry.

[8]  Yan Li,et al.  Stereoselective synthesis and antifungal activities of (E)-alpha-(methoxyimino)benzeneacetate derivatives containing 1,3,5-substituted pyrazole ring. , 2006, Journal of agricultural and food chemistry.

[9]  M. Prudhomme,et al.  Synthesis and antiproliferative activities of diversely substituted glycosyl-isoindigo derivatives. , 2006, European journal of medicinal chemistry.

[10]  S. Bekešová,et al.  Synthesis of 1-Glycosyl Derivatives of Benzocamalexin. , 2005 .

[11]  Paolo Piccardi,et al.  Synthesis and herbicidal activity of novel heterocyclic protoporphyrinogen oxidase inhibitors. , 2004, Pest management science.

[12]  Kathleen A. Durkin,et al.  GABA receptor antagonists and insecticides: common structural features of 4-alkyl-1-phenylpyrazoles and 4-alkyl-1-phenyltrioxabicyclooctanes. , 2004, Bioorganic & medicinal chemistry.

[13]  M. Prudhomme,et al.  Synthesis of glycosyl-isoindigo derivatives , 2004 .

[14]  R. Miethchen.  Modified natural substances—fluorinated and fluoroalkylated monosaccharides and inositols , 2004 .

[15]  S. Bekešová,et al.  Synthesis of 1-Glycosyl Derivatives of Benzocamalexin , 2004 .

[16]  Robert E. Johnson,et al.  Ethyl Pyrrole‐2‐Carboxylate , 2003 .

[17]  M. Preobrazhenskaya,et al.  Synthesis of 1-N-(β-D-Glucopyranosyl)- and 1-N-(1-Deoxy-2,3,4,5,6-penta-O-acetyl-D-galactit-1-yl)ascorbigens , 2002 .

[18]  Thomas Ryckmans,et al.  First dual NK(1) antagonists-serotonin reuptake inhibitors: synthesis and SAR of a new class of potential antidepressants. , 2002, Bioorganic & Medicinal Chemistry Letters.

[19]  J. A. Spicer,et al.  Structure-activity relationships for pyrido-, imidazo-, pyrazolo-, pyrazino-, and pyrrolophenazinecarboxamides as topoisomerase-targeted anticancer agents. , 2002, Journal of medicinal chemistry.

[20]  Miho Mori,et al.  Application of Phosphonium Salts to the Reactions of Various Kinds of Amides , 2001 .

[21]  M. Hein,et al.  Liquid crystals based on fluorinated carbohydrates. , 2000, Carbohydrate research.

[22]  M. Malamas,et al.  Novel benzofuran and benzothiophene biphenyls as inhibitors of protein tyrosine phosphatase 1B with antihyperglycemic properties. , 2000, Journal of medicinal chemistry.

[23]  V. Nenajdenko,et al.  Methods for the synthesis of α,β-unsaturated trifluoromethyl ketones and their use in organic synthesis , 1999 .

[24]  G. Perra,et al.  Antimicrobial and antineoplastic activities of new 4-diazopyrazole derivatives , 1998 .

[25]  M. A. McClinton,et al.  Trifluoromethylations and related reactions in organic chemistry , 1992 .

[26]  P. Ruminski,et al.  Specificity of pyridinemonocarboxylates and benzoic acid analogs as chemical hybridizing agents in wheat , 1991 .

[27]  P. Fischer,et al.  Trihaloacetylated enol ethers : general synthetic procedure and heterocyclic ring closure reactions with hydroxylamine , 1991 .

[28]  John T. Welch,et al.  Fluorine in bioorganic chemistry , 1991 .

[29]  J. Welch.  Advances in the Preparation of Biologically Active Organofluorine Compounds , 1987 .

[30]  R. Masuda,et al.  A Convenient Synthetic Method for β‐Alkoxy‐ and β‐Phenoxyacrylic Acids and 3,4‐Dihydro‐2H‐pyran‐5‐ and 2,3‐Dihydrofuran‐4‐carboxylic Acids. , 1987 .

[31]  J. Welch.  Tetrahedron report number 221 , 1987 .

[32]  R. Masuda,et al.  A Convenient Synthetic Method for β-Alkoxy- and β-Phenoxyacrylic Acids and 3,4-Dihydro-2H-pyran-5- and 2,3-Dihydrofuran-4-carboxylic Acids , 1986 .

[33]  E. Borenfreund,et al.  A simple quantitative procedure using monolayer cultures for cytotoxicity assays (HTD/NR-90) , 1985 .

[34]  B. Trost,et al.  A biomimetic approach to plumericin , 1983 .

[35]  T. Ziegler,et al.  ENOL ETHERS. XIII. ACYLATION OF ENOL ETHERS WITH REACTIVE CARBONYL CHLORIDES , 1982 .

[36]  R. Masuda,et al.  ELECTROPHILIC SUBSTITUTIONS OF OLEFINIC HYDROGENS II. ACYLATION OF VINYL ETHERS AND N-VINYL AMIDES , 1976 .

[37]  R. Davies,et al.  Substituted glycosylamines containing the indole nucleus—II , 1972 .

[38]  Carl Robert Noller,et al.  Chemistry of Organic Compounds , 1951 .