New insight into the chemistry of selenoureas: synthesis and single crystal structural study of diverse derivatives

A series of new heteroatom derivatives of N-acylselenoureas was obtained through the reaction of KSeCN with acyl chloride and primary amines, followed by the cyclisation reaction with phenacyl bromides.

[1]  Xiao-ming Wu,et al.  Recent Advances for the Synthesis of Selenium-containing Small Molecules as Potent Antitumor Agents. , 2018, Current medicinal chemistry.

[2]  B. Banerjee,et al.  Recent developments in the synthesis of biologically relevant selenium-containing scaffolds , 2017 .

[3]  A. Slawin,et al.  Synthesis and Single Crystal Structures of Substituted-1,3-Selenazol-2-amines † , 2016, Molecules.

[4]  C. Sanmartín,et al.  Chalcogen containing heterocyclic scaffolds: New hybrids with antitumoral activity. , 2016, European journal of medicinal chemistry.

[5]  G. Sheldrick Crystal structure refinement with SHELXL , 2015, Acta crystallographica. Section C, Structural chemistry.

[6]  R. Butcher,et al.  Pyridoxine-derived organoselenium compounds with glutathione peroxidase-like and chain-breaking antioxidant activity. , 2014, Chemistry.

[7]  F. Mohr Old Selenium Heterocycles Revisited: Synthesis, Spectroscopic, and Structural Characterization of N‐Acyl‐1,3‐selenazol‐2(3H)‐imines and 5‐Acyl‐1,3‐selenazol‐2‐amines from Acylselenourea Derivatives , 2014 .

[8]  A. Linden,et al.  Intra- and intermolecular Se···X (X = Se, O) interactions in selenium-containing heterocycles: 3-benzoylimino-5-(morpholin-4-yl)-1,2,4-diselenazole. , 2014, Acta crystallographica. Section C, Structural chemistry.

[9]  L. Savegnago,et al.  Involvement of the dopaminergic and serotonergic systems in the antidepressant-like effect caused by 4-phenyl-1-(phenylselanylmethyl)-1,2,3-triazole. , 2013, Life sciences.

[10]  Yu-Guang Wang,et al.  Organic selenium resin in solid phase synthesis and its application in constructing medicinally relevant small organic molecules. , 2013, Mini reviews in medicinal chemistry.

[11]  M. Minoura,et al.  One-pot copper-catalyzed tandem addition-cyclization of 2-iodoanilines with isoselenocyanates for the practical preparation of 2-aminobenzoselenazoles , 2011 .

[12]  T. Wirth Organoselenium Chemistry: Modern Developments In Organic Synthesis , 2010 .

[13]  A. Slawin,et al.  Automated chemical crystallography. , 2010, Journal of the American Chemical Society.

[14]  A. Linden,et al.  Synthesis of 1,3‐Selenazol‐2(3H)‐imines , 2010 .

[15]  K. Kuča,et al.  Is it possible to guess potential drug activity from its crystal structure , 2009 .

[16]  M. Koketsu,et al.  Synthesis of selenium-containing bicyclic beta-lactams via alkene metathesis. , 2009, Organic & biomolecular chemistry.

[17]  G. Olah,et al.  Efficient green synthesis of a-aminonitriles, precursors of a-amino acids , 2008 .

[18]  A. Slawin,et al.  Synthesis and structure of eight-, nine-, and ten-membered rings with P-Se-Se-P linkages. , 2008, Angewandte Chemie.

[19]  M. Koketsu,et al.  Isoselenocyanates: a powerful tool for the synthesis of selenium-containing heterocycles. , 2007, Molecules.

[20]  M. Koketsu,et al.  The synthesis of 1-thia-6-oxa-6aλ4-seleno-3-azapentalene and a 3H-1,2,4-dithiazole , 2007 .

[21]  H. Aoki,et al.  The Preparation of Acylselenourea and Selenocarbamate Using Isoselenocyanate , 2006 .

[22]  M. Koketsu,et al.  Synthesis of 2-Selenoxoperhydro-1,3-selenazin-4-ones and 2-Selenoxo-1,3-selenazolidin-4-ones via Diselenocarbamate Intermediates , 2006 .

[23]  T. Sakai,et al.  Synthesis of 1,3-Selenazines and 1,3-Selenazolidines via Intramolecular Addition of N-Allylselenoureas , 2006 .

[24]  H. Hamana,et al.  Multicomponent Strecker Reaction under High Pressure , 2005 .

[25]  Maria Cristina Burla,et al.  SIR2004: an improved tool for crystal structure determination and refinement , 2005 .

[26]  R. Gibbs,et al.  Bismuth trichloride catalyzed synthesis of α-aminonitriles , 2004 .

[27]  A. Linden,et al.  Synthesis of 4‐(Phenylamino)quinazoline‐2(1H)‐selones and Diselenides from Isoselenocyanates: Dimroth Rearrangement of an Intermediate , 2004 .

[28]  P. Whanger Selenium and its relationship to cancer: an update† , 2004, British Journal of Nutrition.

[29]  B. Ranu,et al.  Efficient microwave-assisted synthesis of quinolines and dihydroquinolines under solvent-free conditions , 2003 .

[30]  Yuehui Zhou,et al.  Synthesis and reactivity of subvalent compounds. Part 13: Reaction of triethyl orthoformate with amines and selenium: A convenient one-step three-component synthesis for selenoureas , 2003 .

[31]  P. Langer,et al.  Efficient Synthesis of Primary Selenocarboxylic Amides by Reaction of Nitriles with Phosphorous(V) Selenide , 2002 .

[32]  M. Koketsu,et al.  EFFICIENT SYNTHESIS OF SELENOUREAS FROM THE CORRESPONDING CARBODIIMIDES , 2002 .

[33]  K. Nicolaou,et al.  Total synthesis of everninomicin 13,384-1--Part 4: explorations of methodology; stereocontrolled synthesis of 1,1'-disaccharides, 1,2-seleno migrations in carbohydrates, and solution- and solid-phase synthesis of 2-deoxy glycosides and orthoesters. , 2000, Chemistry.

[34]  Yuehui Zhou,et al.  Selenium-Containing Heterocycles from Isoselenocyanates: Synthesis of 1,2,3-Selenadiazole Derivatives , 2000 .

[35]  I. Saiki,et al.  Induction of apoptosis in human gastric adenocarcinoma cells by two novel organoselenium compounds, TS-2 and TS-6. , 1999, Anticancer research.

[36]  H. Hartmann,et al.  PREPARATION AND CHARACTERISATION OF N,N-DISUBSTITUTED 2-AMINO-SELENAZOLES , 1999 .

[37]  M. Koketsu,et al.  Preparation of Isoselenocyanate and Synthesis of Carbodiimide by Oxidation of Selenourea , 1999 .

[38]  M. Hatsu,et al.  Novel compounds, 1,3-selenazine derivatives, as antibacterial agents against Escherichia coli and Staphylococcus aureus. , 1998, Research communications in molecular pathology and pharmacology.

[39]  M. Nishio,et al.  CH/π Interaction in the Crystal Structure of Organic Compounds. A Database Study , 1998 .

[40]  T. Nakajima,et al.  Synthesis and Structure of Telluroamides and Selenoamides. The First Crystallographic Study of Telluroamides , 1997 .

[41]  K. Shimada,et al.  Conversion of amides, N,N,N',N'-tetramethylurea, and esters to the corresponding selenoxo compounds by treatment with bis(trimethylsilyl) selenide and BF3.OEt2 , 1994 .

[42]  Y. Kumar,et al.  Synthesis of 2,4-disubstituted thiazoles and selenazoles as potential antitumor and antifilarial agents: 1. Methyl 4-(isothiocyanatomethyl)thiazole-2-carbamates, -selenazole-2- carbamates, and related derivatives. , 1993, Journal of medicinal chemistry.

[43]  R. Richter,et al.  3-Diethylamino-5-phenyl-1,2,4-diselenazolium-tetrachloroniccolat(II) : Synthese und Struktur , 1992 .

[44]  Jessica Daecher,et al.  Organoselenium Chemistry A Practical Approach , 2016 .

[45]  A. Spek PLATON SQUEEZE: a tool for the calculation of the disordered solvent contribution to the calculated structure factors. , 2015, Acta crystallographica. Section C, Structural chemistry.

[46]  A. Ramazani,et al.  Phosphorus, Sulfur, and Silicon and the Related Elements , 2014 .

[47]  G. Sheldrick A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[48]  M. Koketsu,et al.  A facile preparation of selenohydantoins using isoselenocyanate , 2007 .

[49]  L. Henriksen Preparation of Tetrasubstituted Selenoureas and Pentasubstituted Selenosemicarbazides from Carbon Diselenide , 1982 .