Download PDF
Synthesis 2010(16): 2749-2758  
DOI: 10.1055/s-0029-1218842
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

3-Formylchromones, Acylpyruvates, and Chalcone as Valuable Substrates for the Syntheses of Fused Pyridines

Viktor O. Iaroshenko*a,b, Satenik Mkrtchyanb, Dmitriy M. Volochnyuka,c, Peter Langer*b, Vyacheslav Ya. Sosnovskikh*d, Dmytro Ostrovskyia, Sergii Dudkinb, Anton V. Kotljarove, Mariia Miliutinaf, Iryna Savychf, Andrei A. Tolmacheva,c
a National Taras Shevchenko University, 62 Volodymyrska St., Kyiv-33, 01033, Ukraine
b Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: viktor.iaroshenko@uni-rostock.de; e-Mail: iva108@gmail.com;
c Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
d Department of Chemistry, Ural State University, 51 Lenina Ave., 620083 Ekaterinburg, Russian Federation
e-Mail: vyacheslav.sosnovskikh@usu.ru;
e Institute of Organic and Bioorganic Chemistry, University of Tartu, Jakobi 2, 51014 Tartu, Estonia
f Organic Chemistry Department, National Kharkiv V. N. Karazin University, sq. Svobody 4, Kharkiv-77, 61077, Ukraine
Further Information

Publication History

Received 9 April 2010
Publication Date:
29 June 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

The reaction of electron-rich aminoheterocycles with 1,3-CCC-dielectrophiles, such as 3-formylchromones, acylpyruvates, and chalcone, provided diversely fused pyridines. Starting from 5-amino-1-(2,3-O-isopropylidene-β-d-ribofuranosyl)-1H-pyrazole, nucleosides containing a pyrazolo[3,4-b]pyridine fragment were obtained, which can be considered as adenosine deaminase (ADA) inhibitors.

Key words

aminoheterocycles - 3-formylchromones - acylpyruvates - chalcone - fused pyridines - annulation reaction - nucleosides

    References

  • 1a Ealick SE, Parker WB, Seerist JA, and Sorscher EJ. inventors; WO  2003,035,012. 
  • 1b Matulic-Adamic J. Takahashi K. Chou TC. Gadler H. Price RW. Watanabe KA. Reddy ARV. Kalman TI. J. Med. Chem.  1988,  31:  1642 
    Google Scholar
  • 1c Hackova D. Hocek M. Dvorakova H. Votruba I. Tetrahedron  1999,  55:  11109 
    Google Scholar
  • 1d Koch M, Den H, Jacobus A, Koomen J, Wanner G.-J, Martinus J, and Roelof FW. inventors; WO  2006,027,365. 
  • 1e Erion MDM. Reddy R. J. Am. Chem. Soc.  1998,  120:  3295 
    Google Scholar
  • 1f Veliz EA. Stephens OM. Beal PA. Org. Lett.  2001,  3:  2969 
    Google Scholar
  • 1g Lee S. Park SB. Org. Lett.  2009,  11:  5214 
    Google Scholar
  • 2 Misra RN. Rawlins DB. Xiao H. Shan W. Bursuker I. Kellar KA. Mulheron JG. Sack JS. Tokarski JS. Kimball SD. Webster KR. Bioorg. Med. Chem. Lett.  2003,  13:  1133 
    CrossrefGoogle Scholar
  • 3a Lin R. Connolly PJ. Lu Y. Chiu G. Li S. Yu Y. Huang S. Li X. Emanuel SL. Middleton SA. Gruninger RH. Adams M. Fuentes-Pesquera AR. Greenberger LM. Bioorg. Med. Chem. Lett.  2007,  17:  4297 
    Google Scholar
  • 3b Witherington J. Bordas V. Gaiba A. Garton NS. Naylor A. Rawlings AD. Slingsby BP. Smith DG. Takle AK. Ward RW. Bioorg. Med. Chem. Lett.  2003,  13:  3055 
    Google Scholar
  • 4a Goda FE. Abdel-Azizb AA.-M. Attef OA. Bioorg. Med. Chem.  2004,  12:  1845 
    Google Scholar
  • 4b Foks H. Pancechowska-Ksepko D. Kvdzia A. Zwolska Z. Janowiec M. Augustynowicz-Kopec E. Farmaco  2005,  60:  513 
    Google Scholar
  • 5 Dias LRS. Santos MB. de Albuquerque S. Castro HC. de Souza AMT. Freitas ACC. DiVaio MAV. Cabral LM. Rodriguese CR. Bioorg. Med. Chem.  2007,  15:  211 
    CrossrefPubMedGoogle Scholar
  • 6a de Mello H. Echevarria A. Bernardino AM. Canto-Cavalheiro M. Leon LL. J. Med. Chem.  2004,  47:  5427 
    Google Scholar
  • 6b Bharate SB. Mahajan TR. Gole YR. Nambiar M. Matan TT. Kulkarni-Almeida A. Balachandran S. Junjappa H. Balakrishnan A. Vishwakarma RA. Bioorg. Med. Chem.  2008,  16:  7167 
    Google Scholar
  • 7a Haas G. Stanton JL. von Sprecher A. Wenk P.
    J. Heterocycl. Chem.  1981,  18:  607 
    Google Scholar
  • 7b Quiroga J. Mejía D. Insuasty B. Abonía R. Nogueras M. Sánchez A. Cobo J. Low JN. J. Heterocycl. Chem.  2002,  39:  51 
    Google Scholar
  • 7c Ghosh T. Bandyopadhyay C. J. Heterocycl. Chem.  2006,  43:  1431 
    Google Scholar
  • 7d Stankovičová H. Gáplovský A. Lácová M. Chovancová J. Puchaa A. J. Heterocycl. Chem.  2006,  43:  843 
    Google Scholar
  • 7e Chebanov VA. Sakhno YI. Desenko SM. Chernenko VN. Musatov VI. Shishkina SV. Shishkin OV. Kappe CO. Tetrahedron  2007,  63:  1229 
    Google Scholar
  • 8a Ryabukhin SV. Plaskon AS. Volochnyuk DM. Pipko SE. Tolmachev AA. Heterocycles  2008,  75:  583 
    Google Scholar
  • 8b Randhavane PV. Kale SB. Jagdhani SG. Karale BK. Indian J. Heterocycl. Chem.  2007,  17:  153 
    Google Scholar
  • 8c Sonawane SA. Karale BK. Shingare MS. Indian J. Heterocycl. Chem.  2004,  14:  155 
    Google Scholar
  • 9a Plaskon AS. Ryabukhin SV. Volochnyuk DM. Gavrilenko KS. Shivanyuk AN. Tolmachev AA. J. Org. Chem.  2008,  73:  6010 
    Google Scholar
  • 9b Ryabukhin SV. Plaskon AS. Volochnyuk DM. Tolmachev AA. Synthesis  2007,  1861 
    Google Scholar
  • 10a Sosnovskikh VYa. Irgashev RA. Kodess MI. Tetrahedron  2008,  64:  2997 
    Google Scholar
  • 10b Sosnovskikh VYa. Khalymbadzha IA. Irgashev RA. Slepukhin PA. Tetrahedron  2008,  64:  10172 
    Google Scholar
  • 11a Wang X.-S. Zhang M.-M. Li Q. Yao C.-S. Tu S.-J. Synth. Commun.  2008,  38:  1896 
    Google Scholar
  • 11b Shi D.-Q. Ni S.-N. Yang F. Shi J.-W. Dou G.-L. Li X.-Y. Wang X.-S. Ji S.-J. J. Heterocycl. Chem.  2008,  45:  693 
    Google Scholar
  • 12 Goswami S. Jana S. Hazra A. Adak AK. J. Heterocycl. Chem.  2007,  44:  1191 
    CrossrefGoogle Scholar
  • 13 Cho CS. Kim JU. Tetrahedron Lett.  2007,  48:  3775 
    CrossrefGoogle Scholar
  • 14a Iaroshenko VO. Wang Y. Sevenard DV. Volochnyuk DM. Synthesis  2009,  1851 
    Google Scholar
  • 14b Iaroshenko VO. Volochnyuk DM. Kryvokhyzha NV. Martyloga A. Sevenard DV. Groth U. Brand J. Chernega AN. Shivanyuk AN. Tolmachev AA. Synthesis  2008,  2337 
    Google Scholar
  • 15a Iaroshenko VO. Sevenard DV. Volochnyuk DM. Wang Y. Martiloga A. Tolmachev AA. Synthesis  2009,  1865 
    Google Scholar
  • 15b Volochnyuk DM. Pushechnikov AO. Krotko DG. Sibgatulin DA. Kovalyova SA. Tolmachev AA. Synthesis  2003,  1531 
    Google Scholar
  • 15c Iaroshenko VO. Sevenard DV. Kotljarov AV. Volochnyuk DM. Tolmachev AA. Sosnovskikh VYa. Synthesis  2009,  731 
    Google Scholar
  • 16 Iaroshenko VO. Groth U. Kryvokhyzha NV. Obeid S. Tolmachev AA. Wesch T. Synlett  2008,  343 
    Article in Thieme ConnectGoogle Scholar
  • 17 Easterwood LM. Véliz EA. Beal PA. J. Am. Chem. Soc.  2000,  122:  11537 
    CrossrefGoogle Scholar
  • 18a Véliz EA. Easterwood LM. Beal PA. J. Am. Chem. Soc.  2003,  125:  10867 
    Google Scholar
  • 18b Cristalli G. Eleuteri A. Vittori S. Volpini R. Camaioni E. Lupidi G. Drug Dev. Res.  1993,  28:  253 
    Google Scholar
  • 18c Lupidi G. Marmocchi F. Cristalli G. Biochem. Mol. Biol.  1998,  46:  1071 
    Google Scholar
  • 18d Lupidi G. Cristalli G. Marmocchi F. Riva F. Grifantini M.
    J. Enzyme Inhib. Med. Chem.  1985,  1:  67 
    Google Scholar
  • 18e Okamoto A. Tanaka K. Saito I. Bioorg. Med. Chem. Lett.  2002,  12:  97 
    Google Scholar