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European journal of medicinal chemistry v.143, 2018년, pp.1744 - 1756   SCI SCIE
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Green, unexpected synthesis of bis-coumarin derivatives as potent anti-bacterial and anti-inflammatory agents

Chougala, Bahubali M. (Department of Chemistry, Karnatak University, Dharwad, 580 003, Karnataka, India ) ; Samundeeswari, S. (Department of Chemistry, Karnatak University, Dharwad, 580 003, Karnataka, India ) ; Holiyachi, Megharaja (Department of Chemistry, Karnatak University, Dharwad, 580 003, Karnataka, India ) ; Naik, Nirmala S. (Department of Chemistry, Karnatak University, Dharwad, 580 003, Karnataka, India ) ; Shastri, Lokesh A. (Department of Chemistry, Karnatak University, Dharwad, 580 003, Karnataka, India ) ; Dodamani, Suneel (Dr. Prabhakar Kore Basic Science Research Center, KLE University, Belagavi, 590010, Karnataka, India ) ; Jalalpure, Sunil (Dr. Prabhakar Kore Basic Science Research Center, KLE University, Belagavi, 590010, Karnataka, India ) ; Dixit, Sheshagiri R. (Novel Drug Design and Discovery Laboratory, Department of Pharmaceutical Chemistry, S.E.T's College of Pharmacy, Sangolli Rayanna Nagar, Dharwad, 580002, Karnataka, India ) ; Joshi, Shrinivas D. (Novel Drug Design and Discovery Laboratory, Department of Pharmaceutical Chemistry, S.E.T's College of Pharmacy, Sangolli Rayanna Nagar, Dharwad, 580002, Karnataka, India ) ; Sunagar, Vinay A. (Department of Chemistry, G.S.S. C ) ;
  • 초록  

    Abstract A green and efficient protocol has been developed and a series of coumarin based pyrano[3,2- c ]chromene derivatives ( 2 ) have been synthesized using multi-component reaction (MCR) approach. Unexpected 3-coumarinyl-3-pyrazolylpropanoic acids ( 3 ) and C 4 -C 4 chromenes ( 5 ) have been isolated instead of expected product 4 by the reaction of compound ( 2 ) in formic acid at 90 °C for about 4–5 h and at 130 °C for about 8–10 h respectively. Further, C 4 -C 4 chromenes ( 5 ) formation was confirmed by intramolecular cyclization of compounds ( 3 ). These compounds were screened for their biological activities and most of them exhibited promising antibacterial activity. The anti-inflammatory assay was evaluated against HRBC membrane stabilization method and the compounds exhibit excellent anti-inflammatory activity. Molecular docking study has been performed for all the synthesized compounds with Klebsiella pneumoni ae acetolactate synthase and results obtained are quite promising. Highlights Synthesis of coumarin based pyrano[3,2- c ]chromene derivatives were achieved in good to excellent yields underone-pot three component green method. The unexpected 3-coumarinyl-3-pyrazolylpropanoic acids (3) and C 4 -C 4 chromene derivatives (5) have been isolated by the reaction of compound (2) in acidic conditions. All the newly synthesized polyfunctionalized coumarin based pyrano[3,2- c ]chromenes are potent antibacterial and anti-inflammatory agents compared to standard. The molecular docking study reveals that, all newly synthesized polyfunctionalized coumarin based pyrano[2,3- c ]pyrazoles are well supported for invitro antibacterial activity. Graphical abstract [DISPLAY OMISSION]


  • 주제어

    L-proline .   Pyrano[3,2-c]chromene .   Protein denaturation .   HRBC membrane.  

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