Download PDF
Synthesis 2011(3): 419-430  
DOI: 10.1055/s-0030-1258374
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Convenient Synthesis of a Library of Lactam-Fused β-Carbolines via the Ugi Reaction [¹]

Samiran Hutait, Maloy Nayak, Ashok Penta, Sanjay Batra*
Medicinal and Process Chemistry Division, Central Drug Research Institute (CSIR), PO Box 173, Lucknow 226 001, India
Fax: +91(522)2623405; Fax: +91(522)2623938; e-Mail: batra_san@yahoo.co.uk;
Further Information

Publication History

Received 2 November 2010
Publication Date:
20 December 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

We present a convenient synthesis of a chemical library of lactam-fused β-carbolines via a Ugi four-center three-component reaction employing [1-formyl-3-(methoxycarbonyl)-9H-pyrido[3,4-b]indol-9-yl]acetic acid or (1-formyl-9H-pyrido[3,4-b]indol-9-yl)acetic acid, amines and isonitriles.

Key words

Ugi reaction - multicomponent reactions - β-carbolines

1

CDRI Communication No. 7998.

    References

  • Selected references only:
  • 3a Cao R. Peng W. Wang Z. Xu A. Curr. Med. Chem.  2007,  14:  479 ; and references cited therein
    Google Scholar
  • 3b Cao R. Guan X. Shi B. Chen Z. Ren Z. Peng W. Song H. Eur. J. Med. Chem.  2010,  45:  2503 
    Google Scholar
  • 3c Ma C. Cao R. Shi B. Li S. Chen Z. Yi W. Peng W. Ren Z. Song H. Eur. J. Med. Chem.  2010,  45:  1515 
    Google Scholar
  • 3d Chen Z. Cao R. Shi B. Yi W. Yu L. Song H. Ren Z. Peng W. Bioorg. Med. Chem. Lett.  2010,  20:  3876 
    Google Scholar
  • 3e Wu Q. Cao R. Feng M. Guan X. Ma C. Liu J. Song H. Peng W. Eur. J. Med. Chem.  2009,  44:  533 
    Google Scholar
  • 3f Kumar R. Gupta L. Pal P. Khan S. Singh N. Katiyar SB. Meena S. Sarkar J. Sinha S. Kanaujiya JK. Lochab S. Trivedi AK. Chauhan PMS. Eur. J. Med. Chem.  2010,  45:  2265 
    Google Scholar
  • 3g Wu J. Zhao M. Qian K. Lee KH. Morris-Natschke S. Peng S. Eur. J. Med. Chem.  2009,  44:  4153 
    Google Scholar
  • 3h Rook Y. Schmidtke KU. Gaube F. Schepmann D. Wunsch B. Heilmann J. Lehmann J. Winckler T. J. Med. Chem.  2010,  53:  3611 
    Google Scholar
  • 3i Jiao WH. Gao H. Li CY. Zhao F. Jiang RW. Wang Y. Zhou GX. Yao XS. J. Nat. Prod.  2010,  73:  167 
    Google Scholar
  • 3j Inman WD. Bray WM. Gassner NC. Lokey RS. Tenney K. Shen YY. TenDyke K. Suh T. Crews P. J. Nat. Prod.  2010,  73:  255 
    Google Scholar
  • 3k Soriano-Agaton F. Lagoutte D. Poupon E. Roblot F. Fournet A. Gantier JC. Hocquemiller R. J. Nat. Prod.  2005,  68:  1581 
    Google Scholar
  • 3l Kuo PC. Shi LS. Damu AG. Su CR. Huang CH. Ke CH. Wu JB. Lin AJ. Bastow KF. Lee KH. Wu TS. J. Nat. Prod.  2003,  66:  1324 
    Google Scholar
  • 3m Anderson LA. Harris A. Phillipson JD. J. Nat. Prod.  1983,  46:  374 
    Google Scholar
  • 3n Rowinsky EK. Donehower RC. In Cancer Chemotherapy and Biotherapy   Chabner BA. Longo DL. Lippincott-Raven Publishers; Philadelphia: 1996.  p.263 
    Google Scholar
  • 4a Singh V. Hutait S. Batra S. Eur. J. Org. Chem.  2009,  6211 
    Google Scholar
  • 4b Singh V. Hutait S. Biswas S. Batra S. Eur. J. Org. Chem.  2010,  531 
    Google Scholar
  • 4c Singh V. Hutait S. Batra S. Eur. J. Org. Chem.  2010,  3684 
    Google Scholar
  • 4d Hutait S. Singh V. Batra S. Eur. J. Org. Chem.  2010,  6269 
    Google Scholar
  • 4e Hutait S. Batra S. Tetrahedron Lett.  2010,  51:  5781 
    Google Scholar
  • 5a Dömling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
    Google Scholar
  • 5b Nair V. Rajesh C. Vinod AU. Bindu S. Sreekanth AR. Mathen JS. Balagopal L. Acc. Chem. Res.  2003,  36:  899 
    Google Scholar
  • 5c Dömling A. Chem. Rev.  2006,  106:  17 
    Google Scholar
  • 5d Multicomponent Reactions   Zhu J. Bienaymé H. Wiley-VCH; Weinheim: 2005. 
    Google Scholar
  • 5e Lamberth C. Jeanguenat A. Cederbaum F. De Mesmaeker A. Zeller M. Kempf H.-J. Zeun R. Bioorg. Med. Chem.  2008,  16:  1531 
    Google Scholar
  • 5f Toure BB. Hall DG. Chem. Rev.  2009,  109:  4439 
    Google Scholar
  • 6 Zhang J. Jacobson A. Rusche JR. Herlihy W. J. Org. Chem.  1999,  64:  1074 
    CrossrefGoogle Scholar
  • 7a Potapov VV. Fetisova NA. Nikitin AV. Ivachtchenko AV. Tetrahedron Lett.  2009,  50:  2790 ; and references cited therein
    Google Scholar
  • 7b Ilyn AP. Trifilenkov AS. Kuzovkova JA. Kutepov SA. Nikitin AV. Ivachtchenko AV. J. Org. Chem.  2005,  70:  1478 
    Google Scholar
  • 8 Ghandi M. Zarezadeh N. Taheri A. Tetrahedron  2010,  66:  8231 
    CrossrefGoogle Scholar
  • 9a Nayak M. Kanojiya S. Batra S. Synthesis  2009,  431 
    Google Scholar
  • 9b Nayak M. Batra S. Tetrahedron Lett.  2010,  51:  510 
    Google Scholar
1

CDRI Communication No. 7998.

2

Graduate Trainee from the National Institute of Pharmaceutical Education and Research, Raebareli, India.