3-{[1-(2,3,5-Tri-O-benzoyl-β-d-ribofur­an­os-1-yl)-1H-1,2,3-triazol-4-yl]meth­yl}quin­a­zolin-4(3H)-one

Abdelaaziz Ouahrouch; Moha Taourirte; Mohamed El Azhari; Mohamed Saadi; Lahcen El Ammari

doi:10.1107/S1600536812042778

. 2012 Oct 20;68(Pt 11):o3166. doi: 10.1107/S1600536812042778

3-{[1-(2,3,5-Tri-O-benzoyl-β-d-ribofuranos-1-yl)-1H-1,2,3-triazol-4-yl]methyl}quinazolin-4(3H)-one

Abdelaaziz Ouahrouch ^a, Moha Taourirte ^a, Mohamed El Azhari ^b, Mohamed Saadi ^c, Lahcen El Ammari ^c,^*

PMCID: PMC3515260 PMID: 23284480

Abstract

In the compound, C₃₇H₂₉N₅O₈, the quinazoline residue forms a dihedral angle of 72.90 (9)° with the triazole ring. The furan ring adopts a twist conformation. In the crystal, the molecules are linked by non-classical C—H⋯N and C—H⋯O hydrogen bonds, building an infinite three-dimensional network.

Related literature

For details of the synthesis, see: Ines et al. (2008 ▶); Krim et al. (2009 ▶); Huisgen (1963 ▶), Wu et al. (2004 ▶). For background to the biological activity of quinazolines, see: Traxler (1998 ▶); Bridges (2001 ▶); Wakeling (2005 ▶); Diana & Nitz (1993 ▶); Chen et al. (2000 ▶); Manfredini et al. (2000 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₃₇H₂₉N₅O₈
M _r = 671.65
Monoclinic,
a = 11.2646 (2) Å
b = 5.6471 (1) Å
c = 25.7507 (4) Å
β = 99.595 (1)°
V = 1615.15 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.33 × 0.29 × 0.25 mm

Data collection

Bruker X8 APEXII diffractometer
26180 measured reflections
4490 independent reflections
3651 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.081
S = 1.03
4490 reflections
451 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia,1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(39.2KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812042778/bt6845sup1.cif

e-68-o3166-sup1.cif^{(39.2KB, cif)}

Click here for additional data file.^{(215.5KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042778/bt6845Isup2.hkl

e-68-o3166-Isup2.hkl^{(215.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O6ⁱ	0.93	2.57	3.483 (3)	168
C13—H13⋯O6ⁱⁱ	0.98	2.36	3.293 (3)	159
C6—H6⋯N1ⁱⁱⁱ	0.93	2.62	3.390 (3)	141

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

supplementary crystallographic information

Comment

Quinazoline and its derivatives are an interesting class of heterocyclic compounds that have drawn much attention because of their biological and pharmaceutical activities including a wide range of antitumor activity (Traxler, 1998; Bridges, 2001; Wakeling, 2005). Furthermore, triazole heterocycles are potent antiviral (Diana & Nitz, 1993), antimicrobial (Chen et al., 2000), and anti-proliferate agents (Manfredini et al., 2000). The pharmaceutical importance of triazoles has prompted the design and synthesis of various triazolonucleosides.

The most interesting method for the synthesis of triazoles is the Huisgen 1,3-dipolar cycloaddition of organic azides with alkynes (Huisgen, 1963). Copper-catalyzed click chemistry is an efficient method that uses azides and terminal acetylenes to have 1,4-disubstituted-1,2,3- triazole products with excellent selectivity and high yield (Wu et al., 2004). In connection to our studies on the synthesis of new nucleosides, we decided to explore the feasibility of the 'click' chemistry for the synthesis of novel 1,2,3-triazoles containing the quinazolinone moiety.

The molecule of the title compound contains a quinazolinone moiety linked to a furan ring through a triazole ring. As shown in Fig.1, the furan ring is also connected to three benzoyl rings. The furan ring which adopts a twist conformation as indicated by Cremer & Pople (1975) puckering parameters Q(2)= 0.365 (2) Å and the phase angle φ = 85.7 (3)°. The five-membered ring (O2 C12 C13 C22 C30) is nearly perpendicular to (N3 N4 N5 C10 C11), (C16 to C21), (C24 to C29) and to (C32 to C37) with the dihedral angles of 79.6 (2), 75.9 (2), 83.4 (2) and 88.2 (2)°, respectively.

An intermolecular C–H···N and C–H···O non classic hydrogen bonds, building an infinite three-dimensional network ensure the cohesion of the crystal structure (see Table 1).

Experimental

The title compound, 3-((2,3,5-tri-O-benzoyl-β-D-ribofuranosyl- 1H-1,2,3-τriazol-4-yl)methyl) quinazolin-4(3H)-one was achieved by cycloaddition of propargylated quinazolinone with 2,3,5-tri-O-benzoyl-β-D– ribofuranosyl azide under microwave conditions with CuI as catalyst and without solvent. The product was obtained with quantitative yield (84%) and short reaction time (Ines et al. (2008); Krim et al. (2009)). The crude product was purified passing through a column packed with silica gel. Crystal suitable for X-ray analysis was obtained by slow evaporation of a methanol.