3-[4-(10H-Indolo[3,2-b]quinolin-11-yl)piperazin-1-yl]propan-1-ol

In the title compound, C22H24N4O, the aromatic moiety is essentially planar (r.m.s. deviation of a least-squares plane fitted through all non-H atoms = 0.0386 Å) and is rotated by 89.98 (4)° from the piperazine ring, which adopts the expected chair conformation. The propanol chain is not fully extended away from the piperazine ring. In the crystal, there are two unique hydrogen-bonding interactions. One is an O—H⋯N interaction which, together with an inversion-related symmetry equivalent, forms a ring motif. The second is an N—H⋯N interaction which links adjacent molecules by means of a chain motif which propagates in the c-axis direction. Overall, a two-dimensional hydrogen-bonded structure is formed.

In the title compound, C 22 H 24 N 4 O, the aromatic moiety is essentially planar (r.m.s. deviation of a least-squares plane fitted through all non-H atoms = 0.0386 Å ) and is rotated by 89.98 (4) from the piperazine ring, which adopts the expected chair conformation. The propanol chain is not fully extended away from the piperazine ring. In the crystal, there are two unique hydrogen-bonding interactions. One is an O-HÁ Á ÁN interaction which, together with an inversion-related symmetry equivalent, forms a ring motif. The second is an N-HÁ Á ÁN interaction which links adjacent molecules by means of a chain motif which propagates in the c-axis direction. Overall, a two-dimensional hydrogen-bonded structure is formed.
Ou, T. M., Lu, Y. J., Zhang, C., Huang, Z. S., Wang, X. D., Tan  We have used quindoline as a scaffold for lead modification and synthesis of c-Myc G-quadruplex stabilizing compounds. We postulated that the addition of piperazine ring would provide steric bulk to the planar quindoline ring resulting in increased selectivity for G-quadruplex binding over duplex DNA. The title compound was synthesized starting from 11-chloroquindoline and tested for its ability to interact with c-Myc G-quadruplex. Anthranilic acid and aniline were used in a multistep procedure to synthesize 11-chloroquindoline as reported in literature (Bierer et al., 1998;Takeuchi et al., 1997).
The molecular structure of (I) is shown in Figure 1. Molecular dimensions are unexceptional. The aromatic moiety of the structure is essentially planar (a mean plane fitted through all non-hydrogen atoms of the moiety has an r.m.s. deviation of 0.0386 Å). This plane is rotated by 89.98 (4)° from the piperazine ring, which adopts an expected chair conformation.
The propanol chain is not fully extended away from the piperazine ring.
The compound has a two-dimensional hydrogen-bonded structure ( Figure 2). Two O-H···N interactions, which are symmetry related by an inversion centre, form an R 2 2 (12)motif (Bernstein et al., 1995) while further N-H···N interactions link adjacent molecules into by means of a C(5) motif in the c-axis direction.