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

Jean Guillon (1) , Stéphane Moreau (1) , Vanessa Desplat (2) , Marian Vincenzi (1) , Noël Pinaud (3) , Solène Savrimoutou (1) , Sandra Rubio (1) , Luisa Ronga (1) , Filomena Rossi (4) , Mathieu Marchivie (5)

1 ARNA - Acides Nucléiques : Régulations Naturelle et Artificielle
2 Cellules souches hématopoïétiques normales et leucémiques
3 ISM - Institut des Sciences Moléculaires
4 University of Naples Federico II = Università degli studi di Napoli Federico II
5 ICMCB - Institut de Chimie de la Matière Condensée de Bordeaux

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).

Mots clés: Antileukemial; Pyrrolo[2; 3-c]quinoline; Heterocycle

Domaines: Chimie thérapeutique; Cristallographie

Jean Guillon, Stéphane Moreau, Vanessa Desplat, Marian Vincenzi, Noël Pinaud, 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. Journal of Chemical Crystallography, 2019, 49 (2), pp.106-112. ⟨10.1007/s10870-018-0734-2⟩. ⟨hal-02130098⟩