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Serendipitous formation of novel class of dichromeno pyrano pyrimidinone derivatives possessing anti-tubercular activity against M. tuberculosis H37Rv

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Abstract

One pot three-component reaction of salicylaldehyde, barbituric acid, and 4-OH coumarin catalyzed by ionic liquid, 1-(ethylaceto acetate)-1-(2-hydroxyethyl) piperidinium tetrachloroaluminate [EAHEPiPY]+ [AlCl4] in water resulted into unexpected formation of a novel class of dichromeno pyrano pyrimidinone derivatives. Synthesized compounds exhibited excellent in vitro anti-tubercular activity against M. tuberculosis H37Rv.

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References

  • Abdolmohammadi S, Balalaie S (2007) Novel and efficient catalysts for the one-pot synthesisof 3,4-dihydropyrano[c]chromene derivatives in aqueous media. Tetrahedron Lett 48:3299–3303

    Article  CAS  Google Scholar 

  • Adib M, Sheikhi E, Kavoosi A, Bijanzadeh HR (2010) Synthesis of 2-(alkylamino)-5-{alkyl[(2-oxo-2H-chromen-3-yl)carbonyl]amino}-3,4-furandicarboxylates using a multi-component reaction in water. Tetrahedron 66:9263–9269

    Article  CAS  Google Scholar 

  • Chen WB, Wu ZJ, Pei QL, Cun LF, Zhang XM, Yuan WC (2010) Highly enantioselective construction of spiro[4H-pyran-3,3′-oxindoles] through a domino Knoevenagel/Michael/Cyclization sequence catalyzed by cupreine. Org Lett 12:3132–3135

    Article  CAS  PubMed  Google Scholar 

  • Dige NC, Korade SN, Pore DM (2017) Design of task-specific ionic liquid, 1-(ethylaceto acetate)-1-(2-hydroxyethyl) piperidinium tetrachloroaluminate for multicomponent synthesis of 3,3′-disubstituted oxindoles. Res Chem Intermed. http://doi.org/10.1007/s11164-017-3034-0

  • Domling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106:17–89

    Article  PubMed  Google Scholar 

  • Evdokimov NM, Kireev AS, Yakovenko AA, Antipin MY, Magedov IV, Kornienko A (2007) One-step synthesis of heterocyclic privileged medicinal scaffolds by a multicomponent reaction of malononitrile with aldehydes and thiols. J Org Chem 72:3443–3453

    Article  CAS  PubMed  Google Scholar 

  • Ghosh PP, Das AR (2013) Nanocrystalline and reusable ZnO catalyst for the assembly of densely functionalized 4H-chromenes in aqueous medium via one-pot three component reactions: a greener “NOSE” approach. J Org Chem 78:6170–6181

    Article  CAS  PubMed  Google Scholar 

  • Gong K, Wang H, Luo J, Liu ZJ (2009) One-pot synthesis of polyfunctionalized pyrans catalyzed by basic ionic liquid in aqueous media. Heterocycl Chem 46:1145–1150

    Article  CAS  Google Scholar 

  • Haveliwala DD, Kamdar NR, Mistry PT, Patel SKJ (2011) Synthesis of novel thiopyrimidines: an investigation of anti-tubercular and antimicrobial activity. Sulfur Chem 32:451–462

    Article  CAS  Google Scholar 

  • Heravi MM, Jani BA, Derikvand F (2008) Three component, one-pot synthesis of dihydropyrano[3,2-c]chromene derivatives in the presence of H6P2W18O62 • 18H2O as a green and recyclable catalyst. Catal Commun 10:272–275

    Article  CAS  Google Scholar 

  • Isambert N, Duque M, del MS, Plaquevent JC, Genisson Y, Rodriguez J, Constantieux T (2011) Multicomponent reactions and ionic liquids: a perfect synergy for eco-compatible heterocyclic synthesis. Chem Soc Rev 40:1347–1357

    Article  CAS  PubMed  Google Scholar 

  • Kalinski C, Umkehrer M, Weber L, Kolb J, Burdack C, Ross G (2010) On the industrial applications of MCRs: molecular diversity in drug discovery and generic drug synthesis. Mol Divers 14:513–522

    Article  CAS  PubMed  Google Scholar 

  • Kanizsai I, Gyaonfalvi S, Szadonyi Z, Sillanpa R, Fulop F (2007) Synthesis of bi- and tricyclic β-lactam libraries in aqueous medium. Green Chem 9:357–360

    Article  CAS  Google Scholar 

  • Karimi AR, Sedaghatpour F (2010) Novel Mono- and Bis(spiro-2-amino-4H-pyrans): Alum-catalyzed reaction of 4-hydroxycoumarin and malononitrile with isatins, quinones, or ninhydrin. Synthesis 10:1731–1735

    Article  Google Scholar 

  • Kasralikar HM, Jadhavar SC, Bhusare SR (2015) Synthesis and molecular docking study of novel chromeno-chromenones as Anti-HIV-1 NNRT inhibitors. Synlett 26:1969–1672

    Article  CAS  Google Scholar 

  • Khurana JM, Kumar S (2009) Tetrabutylammonium bromide (TBAB): a neutral and efficient catalyst for the synthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives in water and solvent-free conditions. Tetrahedron Lett 50:4125–4127

    Article  CAS  Google Scholar 

  • Khurana JM, Nand B, Saluja P (2010) DBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b]pyranes, 2-amino-4H-benzo[h]chromenes and 2-amino-4H benzo[g]chromenes in aqueous medium. Tetrahedron 66(30):5637–5641

  • Laxmi SV, Reddy YT, Kuarm BS, Reddy PN, Crooks PA, Rajitha B (2011) Synthesis and evaluation of chromenyl barbiturates and thiobarbiturates,as potential antitubercular agents. Bioorg Med Chem Lett 21:4329–4332

    Article  Google Scholar 

  • Lindstrom UM (2007) Organic reactions in water: principles, strategies and applications. Blackwell, Oxford, UK

    Book  Google Scholar 

  • Lourenco MCS, deSouza MVN, Pinheiro AC, Ferreira M, de L, Goncalves RB, Nogneira TCM, Peralta MA (2007) Evaluation of anti-tubercular activity of nicotinic and isoniazidanalogues. ARKIVOC xv:181–19

    Google Scholar 

  • Majumdar N, Paul ND, Mandal S, Bruin B, de, Wulf WD (2015) Catalytic synthesis of 2H-chromenes. ACS Catal 5:2329–2366

    Article  CAS  Google Scholar 

  • Mane MM, Pore DM (2016) Synthesis of 2-Amino-4-(3-amino-5-hydroxy-4H-pyrazol-4-ylidene)-4H-chromene-3-carbonitriles. Synlett 27:1720–1724

    Article  CAS  Google Scholar 

  • Muller FL, Constantieux T, Rodriguez JJ (2005) Multicomponent domino reaction from β-ketoamides: highly efficient access to original polyfunctionalized 2,6-diazabicyclo[2.2.2]octane cores. Am Chem Soc 127:17176–17177

    Article  Google Scholar 

  • Pratap R, Ram VJ (2014) Natural and synthetic chromenes, fused chromenes, and versatility of dihydrobenzo[h]chromenes in organic synthesis. Chem Rev 114:10476–10526

    Article  CAS  PubMed  Google Scholar 

  • Pore PM, Hegade PG, Mane MM, Patil JD (2013) The unprecedented synthesis of novel spiro-1,2,4-triazolidinones. RSC Advances 3(48):25723

  • Reddy DS, Hosamani KM, Devarajegowd HC (2015) Design, synthesis of benzocoumarin-pyrimidine hybrids as novel class of antitubercular agents, their DNA cleavage and X-ray studies. Eur J Med Chem 101:705–715

    Article  CAS  PubMed  Google Scholar 

  • Sameem B, Saeedi M, Mahdavi M, Nadri H, Moghadam FH, Edraki N, Khan MI, Amini M (2017) Synthesis, docking study and neuroprotective effects of some novel pyrano[3,2-c]chromene derivatives bearing morpholine/ phenylpiperazine moiety. Bioorg Med Chem 25:3980–3988

    Article  CAS  PubMed  Google Scholar 

  • Seifi M, Sheibani H (2008) Highly effective heterogeneous base catalyst for three-component synthesis of tetrahydrobenzopyran and 3,4-dihydropyrano[c]chromene derivatives in aqueous media. Catal Lett 126:275–279

    Article  CAS  Google Scholar 

  • Shaabani A, Samadi S, Badri Z, Rahmati A (2005) Ionic liquid promoted efficient and rapid one-pot synthesis of pyranannulated heterocyclic systems. Catal Lett 104:39–43

    Article  CAS  Google Scholar 

  • Singh MS, Chowdhury S (2012) Recent developments in solvent-free multicomponent reactions: a perfect synergy for eco-compatible organic synthesis. RSC Adv 2:4547–4592

    Article  CAS  Google Scholar 

  • Undale K, Park Y, Park K, Dagade D, Pore D (2011) A Revisit to the Hantzsch Reaction: Unexpected Formation of Tetrahydro-benzo[b]pyrans beyond Polyhydroquinolines. Synlett 2011(6):791–796

  • Weber L (2002) Multi-component reactions and evolutionary chemistry. Drug Discov Today 7:143–147

    Article  CAS  PubMed  Google Scholar 

  • Willy B, Muller TJJ (2008) Regioselective three-component synthesis of highly fluorescent 1,3,5-trisubstituted pyrazoles. Eur J Org Chem 2008:4157–4168

  • World Health Organization (WHO) Global tuberculosis report 2015. http://www.who.int/tb/publications/global_report/en/

  • World Health Organization (2008) Guidelines for the programmatic management of drug resistant tuberculosis: emergency update 2008. World Health Organization, Geneva, (WHO/HTM/TB/2008.402)

    Google Scholar 

  • World Health Organization (2009) Treatment of tuberculosis, Guidelines for National Programs. WHO/HTM/TB/2009.420, 4th edn. English

Download references

Acknowledgements

One of the authors NCD is grateful to the University Grants Commission (UGC), New Delhi for providing financial assistance in the form of UGC-BSR-SAP fellowship (F.25–1/2014-15(BSR)/7-183/2009(BSR)–5 November 2015).

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Correspondence to Dattaprasad M. Pore.

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Dige, N.C., Mahajan, P.G. & Pore, D.M. Serendipitous formation of novel class of dichromeno pyrano pyrimidinone derivatives possessing anti-tubercular activity against M. tuberculosis H37Rv. Med Chem Res 27, 224–233 (2018). https://doi.org/10.1007/s00044-017-2062-z

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