Methyl 3-[(6-nitro-4-oxo-3-phenyl-3,4-di­hydro­quinazolin-2-yl)sulfan­yl]propano­ate

Ibrahim A Al-Suwaidan; Alaa A-M Abdel-Aziz; Adel S El-Azab; C S Chidan Kumar; Hoong-Kun Fun

doi:10.1107/S1600536813016127

. 2013 Jun 19;69(Pt 7):o1111. doi: 10.1107/S1600536813016127

Methyl 3-[(6-nitro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)sulfanyl]propanoate

Ibrahim A Al-Suwaidan ^a, Alaa A-M Abdel-Aziz ^a,^b, Adel S El-Azab ^a,^c, C S Chidan Kumar ^d,^‡, Hoong-Kun Fun ^d,^a,^*,^§

PMCID: PMC3770384 PMID: 24046669

Abstract

In the title compound, C₁₈H₁₅N₃O₅S, the approximately planar quinazoline ring system [maximum deviation = 0.097 (3) Å] forms a dihedral angle of 76.53 (19)° with the phenyl ring. The terminal -C(=O)—O—C group is disordered over two sets of sites with a site-occupancy ratio of 0.811 (17):0.189 (17). In the crystal, molecules are linked via weak C—H⋯O hydrogen bonds into sheets parallel to the ac plane.

Related literature

For background to quinazoline chemistry, see: El-Azab (2007 ▶); El-Azab et al. (2010 ▶, 2011 ▶); Alafeefy et al. (2008 ▶); Al-Suwaidan et al. (2013 ▶); El-Azab & ElTahir (2012a ▶,b ▶). For standard bond-length data, see: Allen et al. (1987 ▶). graphic file with name e-69-o1111-scheme1.jpg

Experimental

Crystal data

C₁₈H₁₅N₃O₅S
M _r = 385.39
Monoclinic,
a = 4.9146 (3) Å
b = 26.5065 (18) Å
c = 14.0900 (9) Å
β = 94.645 (4)°
V = 1829.5 (2) Å³
Z = 4
Cu Kα radiation
μ = 1.89 mm⁻¹
T = 296 K
0.32 × 0.26 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.583, T _max = 0.791
12669 measured reflections
3382 independent reflections
1861 reflections with I > 2σ(I)
R _int = 0.059

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.191
S = 1.03
3382 reflections
273 parameters
9 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016127/lh5622sup1.cif

e-69-o1111-sup1.cif^{(29KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016127/lh5622Isup2.hkl

e-69-o1111-Isup2.hkl^{(165.9KB, hkl)}

Click here for additional data file.^{(6.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813016127/lh5622Isup3.cml

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
C6—H6A⋯O2ⁱ	0.93	2.56	3.142 (5)	121
C10—H10A⋯O2ⁱⁱ	0.93	2.39	3.167 (5)	140

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

Acknowledgments

The authors thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University. CSC thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

supplementary crystallographic information

Comment

Quinazolines are considered to be important chemical synthons of physiological significance and pharmaceutical utility. They possess a variety of biological effects including antimicrobial (El-Azab et al., 2007), anti-inflammatory (Alafeefy et al., 2008), anticonvulsant, (El-Azab et al., 2011; El-Azab & ElTahir 2012a,b) and anticancer activities (El-Azab et al., 2010; El-Azab & ElTahir 2012b; Al-Suwaidan et al., 2013). These observations have been the guidelines for the development of new quinazolines which possess varied biological activities. Prompted by the potential biological activities of quinazolines, the title compound was synthesized and its crystal structure is reported herein.

The molecular structure of the title compound is shown in Fig. 1. The quinazoline ring (C1–C8/N1–N2; maximum deviation = 0.097 (3) Å at atom N2) makes a dihedral angle of 76.53 (19)° with the attached phenyl ring (C9–C14). The terminal C17(═O1)—O5—C18 group is disordered over two positions with a site-occupancy ratio of 0.811 (17): 0.189 (17). In the crystal structure (Fig. 2), the molecules are linked via weak intermolecular C6—H6A···O2ⁱ and C10—H10A···O2ⁱⁱ hydrogen bonds (see Table 1 for symmetry codes) into sheets parallel to the ac plane.

Experimental

A mixture of 3-phenyl-2-mercapto-6-nitro-quinazolin-4(3H)-one (2.99 g, 0.01 mol) and Et₃N (2 ml) in CH₂Cl₂ (30 ml) was stirred in an ice bath and acryloyl chloride (3.3 ml, 0.04 mol) was added dropwise over a period of 15 min. Stirring was performed in an ice bath for 1 h and then at room temperature overnight. Solvent was then removed under reduced pressure and the obtained residue was dissolved in CH₂Cl₂ and washed with 10% NaOH solution and water. The resultant was separated and dried over MgSO₄ then evaporated in vacuo. The obtained residue was chromatographed on silica gel using 10% EtOAc/hexane as eluant and recrystallized from hexane/CH₂Cl₂ (92%) (m.p:. 480 K) to yield X-ray quality crystals.