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Synthesis, Crystal Structure and Anti-leukemic Activity of 4-{4-[(4-(2-Oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-3-phenyl-3H-pyrrolo[2,3-c]quinoline

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Abstract

The title compound 4-{4-[(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-3-phenyl-3H-pyrrolo[2,3-c]quinoline 1, a compound that showed cytotoxic potential against two leukemia cell lines, has been synthesized via a multi-step pathway. This compound was characterized by single-crystal X-ray diffraction, IR, MS, elemental analysis, 1H and 13C NMR. The crystal (C37H33H5O, Mr = 563.68) belongs to orthorhombic, space group Pbcn with cell parameters a = 30.198(2) Å, b = 12.5097(11) Å, c = 15.6648(13) Å, V = 5917.7(8) Å3, Z = 8, Dc = 1.265 g/cm3, CuKα radiation, λ = 1.54180 Å, µ = 0.611 mm−1, F(000) = 2384, the final R = 0.0491 and wR = 0.1585 for 5698 observed reflections with I > 2σ(I).

Graphical Abstract

The antileukemial 4-{4-[(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-3-phenyl-3H-pyrrolo[2,3-c]quinoline was synthesized and characterized by X-ray crystallography.

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References

  1. Lichtman MA (2008) Oncologist 13:126

    Article  PubMed  Google Scholar 

  2. Carroll AR, Duffy S, Avery VM (2010) J Org Chem 75:8291

    Article  CAS  PubMed  Google Scholar 

  3. Okanya PW, Mohr KI, Gerth K, Jansen R, Mueller R (2011) J Nat Prod 74:603

    Article  CAS  PubMed  Google Scholar 

  4. Mhaske SB, Lande JR (2013) WO 2013117986

  5. Campos Aguiar AC, Panciera M, Simao dos Santos EF, Singh MK, Garcia ML, Eduardo de Souza G, Nakabashi M, Costa JL, Garcia CRS, Oliva G, Roque Duarte Correia C, Carvalho Guido RV (2018) J Med Chem 61:5547

    Article  CAS  Google Scholar 

  6. Akula M, Sridevi JP, Yogeeswari P, Sriram D, Bhattacharya A (2014) Monatsh Chem 145:811

    Article  CAS  Google Scholar 

  7. Panarese JD, Lindsley CW (2012) Org Lett 14:5808

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Desplat V, Moreau S, Gay A, Belisle-Fabre S, Thiolat D, Massip S, Mossalayi D, Jarry C, Guillon J (2010) J Enzyme Inhib Med Chem 25:204

    Article  CAS  PubMed  Google Scholar 

  9. Desplat V, Moreau S, Belisle-Fabre S, Thiolat D, Uranga J, Lucas R, Massip S, de Moor L, Jarry C, Mossalayi D, Sonnet P, Déléris G, Guillon J (2011) J Enzyme Inhib Med Chem 26:657

    Article  CAS  PubMed  Google Scholar 

  10. Desplat V, Vincenzi M, Lucas R, Moreau S, Savrimoutou S, Pinaud N, Lesbordes J, Peyrilles E, Marchivie M, Routier S, Sonnet P, Rossi F, Ronga L, Guillon J (2016) Eur J Med Chem 113:214

    Article  CAS  PubMed  Google Scholar 

  11. Guillon J, Vincenzi M, Pinaud N, Ronga L, Rossi F, Savrimoutou S, Moreau S, Desplat V, Marchivie M (2016) Struct Chem Crystallogr Commun 2:18

    Google Scholar 

  12. Desplat V, Vincenzi M, Lucas R, Moreau S, Savrimoutou S, Rubio S, Pinaud N, Bigat D, Enriquez E, Marchivie M, Routier S, Sonnet P, Rossi F, Ronga L, Guillon J (2017) ChemMedChem 12:940

    Article  CAS  PubMed  Google Scholar 

  13. Barton DHR, Kervagoret J, Zard SZ (1990) Tetrahedron 46:7587

    Article  CAS  Google Scholar 

  14. Alazard JP, Boye O, Gillet B, Guenard D, Beloeil JC, Thal C (1993) Bull Soc Chim Fr 130:779

    CAS  Google Scholar 

  15. Sheldrick GM (2008) Acta Crystallogr Sect A 64:112

    Article  CAS  Google Scholar 

  16. Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H (2009) J Appl Crystallogr 42:339

    Article  CAS  Google Scholar 

  17. Inaba S, Akatsu M, Hirohashi T, Yamamoto H (1976) Chem Pharm Bull 24:1076

    Article  CAS  PubMed  Google Scholar 

  18. Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor R (1987) J Chem Soc Perkin Trans 2: S1

    Article  Google Scholar 

  19. Kanjana-opas A, Panphon S, Fun HK, Chantrapromma S (2006) Acta Crystallogr Sect E E62:o2728

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This publication was supported by a grant from Ligue Contre le Cancer (Comité Aquitaine-Charentes, Bordeaux, France).

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Authors and Affiliations

  1. Univ. Bordeaux, UFR des Sciences Pharmaceutiques, INSERM U1212 / CNRS UMR 5320, Laboratoire ARNA, 33076, Bordeaux Cedex, France

    Jean Guillon, Stéphane Moreau, Marian Vincenzi, Solène Savrimoutou, Sandra Rubio & Luisa Ronga

  2. Univ. Bordeaux, UFR des Sciences Pharmaceutiques, INSERM U1035, Cellules Souches Hématopoïétiques Normales et Leucémiques, 33076, Bordeaux Cedex, France

    Vanessa Desplat

  3. Univ. Bordeaux, ISM - CNRS UMR 5255, 33405, Talence Cedex, France

    Noël Pinaud

  4. Department of Pharmacy and CIRPeB, University of Naples “Federico II”, 80134, Naples, Italy

    Filomena Rossi

  5. Univ. Bordeaux, ICMCB CNRS-UPR 9048, 33608, Pessac Cedex, France

    Mathieu Marchivie

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  1. Jean Guillon
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  2. Stéphane Moreau
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  3. Vanessa Desplat
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  9. Filomena Rossi
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  10. Mathieu Marchivie
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Correspondence to Jean Guillon.

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Guillon, J., Moreau, S., Desplat, V. et al. Synthesis, Crystal Structure and Anti-leukemic Activity of 4-{4-[(4-(2-Oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-3-phenyl-3H-pyrrolo[2,3-c]quinoline. J Chem Crystallogr 49, 106–112 (2019). https://doi.org/10.1007/s10870-018-0734-2

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  • DOI: https://doi.org/10.1007/s10870-018-0734-2

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