Skip to main content
SpringerLink
Log in

The synthesis of low molecular weight pyrrolo[2,3-c]pyridine-7-one scaffold

  • Full-Length Paper
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

A facile method for the synthesis of substituted pyrrolo[2,3-c]pyridine-7-ones is developed that applies an acid-promoted intramolecular cyclization of 2-pyrrolecarboxylic acid amidoacetals as key step. The synthesis is easily scaled up to 1.5 mol quantity with no yield decrease. The alkylation/arylation reaction of the pyrrolo[2,3-c]pyridine-7-ones proceeds regioselectively giving N6-substituted derivatives.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Rishton GM (2008) Molecular diversity in the context of leadlikeness: compound properties that enable effective biochemical screening. Curr Opin Chem Biol 12: 340–351. doi:10.1016/j.cbpa.2008.02.008

    Article  CAS  Google Scholar 

  2. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (1997) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliver Rev 23: 3–25. doi:10.1016/S0169-409X(96)00423-1

    Article  CAS  Google Scholar 

  3. Rishton GM (1997) Reactive compounds and in vitro false positives in HTS. Drug Discov Today 2: 382–384. doi:10.1016/S1359-6446(97)01083-0

    Article  CAS  Google Scholar 

  4. Roche O, Schneider P, Zuegge J, Guba W, Kansy M, Alanine A, Bleicher K, Danel F, Gutknecht EM, Rogers-Evans M (2002) Development of a virtual screening method for identification of “frequent hitters” in compound libraries. J Med Chem 45: 137–142. doi:10.1021/jm010934d

    Article  CAS  Google Scholar 

  5. Goetz GH, Harrigan GG, Likos J (2001) Ugibohlin: a new dibromo-seco-isophakellin from Axinella carteri. J Nat Prod 64: 1581–1582. doi:10.1021/np010202o

    Article  CAS  Google Scholar 

  6. Assmann M, van Soest RWM, Köck M (2001) New antifeedant bromopyrrole alkaloid from the caribbean sponge Stylissa caribica. J Nat Prod 64: 1345–1347. doi:10.1021/np000482s

    Article  CAS  Google Scholar 

  7. Travert N, Martin M-T, Bourguet-Kondracki M-L, Al-Mourabit A (2005) Regioselective intramolecular N1–C3 cyclizations on pyrrole–proline to ABC tricycles of dibromophakellin and ugibohlin. Tetrahedron Lett 46: 249–252. doi:10.1016/j.tetlet.2004.11.066

    Article  CAS  Google Scholar 

  8. Brimble MA, Brimble MT, Hodges R, Lane GA (1988) Synthesis of 2-methylpyrrolo[1,2-a]pyrazin-1(2H)-one. Aust J Chem 41: 1583–1590. doi:10.1071/CH9881583

    Article  CAS  Google Scholar 

  9. Dumas DJ (1988) Total synthesis of peramine. J Org Chem 53: 4650–4653. doi:10.1021/jo00255a002

    Article  CAS  Google Scholar 

  10. Yakushijin K, Horne D (2000) Controlling cyclizations of 2-pyrrolecarboxamidoacetals. Facile solvation of beta-amido aldehydes and revised structure of synthetic homolongamide. Tetrahedron Lett 41: 4295–4299. doi:10.1016/S0040-4039(00)00630-4

    Article  Google Scholar 

  11. Ducrocq C, Bisagni E, Lhoste J-M, Mispelter J, Defaye J (1976) Aza-indoles—III: synthese de l’amino-4-aza-5-indole et du N-5-ribonucleoside correspondant (iso-deaza-1-tubercidine). Tetrahedron 32: 773–780. doi:10.1016/0040-4020(76)80003-8

    Article  CAS  Google Scholar 

  12. Dzhavakhishvili SG, Gorobets NY, Shishkina SV, Shishkin OV, Desenko SM, Groth UM (2009) Diversification of a thieno[2,3-d]pyrimidin-4-one scaffold via regioselective alkylation reactions. J Comb Chem 11: 508–514. doi:10.1021/cc9000373

    Article  CAS  Google Scholar 

  13. Sirko SM, Gorobets NY, Musatov VI, Desenko SM (2009) Generation of 500-member library of 10-alkyl-2-R1,3-R2-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones. Molecules 14: 5223–5234. doi:10.3390/molecules14125223

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. National University of Pharmacy, Pushkinska Str. 53, Kharkiv, 61002, Ukraine

    Maxim A. Nechayev & Sergiy M. Kovalenko

  2. Laboratory for Physicochemical Processes, SSI ‘Institute for SingleCrystals’ of NAS of Ukraine, Lenina Ave 60, Kharkiv, 61001, Ukraine

    Nikolay Yu. Gorobets

  3. Enamine Ltd., Alexandra Matrosova Street, 23, Kiev, 01103, Ukraine

    Alexander V. Borisov & Andrey A. Tolmachev

Authors
  1. Maxim A. Nechayev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nikolay Yu. Gorobets
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Alexander V. Borisov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sergiy M. Kovalenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Andrey A. Tolmachev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nikolay Yu. Gorobets.

Electronic Supplementary Material

The Below is the Electronic Supplementary Material.

ESM 1 (PDF 4834 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nechayev, M.A., Gorobets, N.Y., Borisov, A.V. et al. The synthesis of low molecular weight pyrrolo[2,3-c]pyridine-7-one scaffold. Mol Divers 16, 749–757 (2012). https://doi.org/10.1007/s11030-012-9410-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-012-9410-1

Keywords

Search

Navigation