N-(4-Hy­droxy­phen­yl)-3,4,5-trimeth­oxy­benzamide

Hyeong Choi; Yong Suk Shim; Byung Hee Han; Sung Kwon Kang; Chang Keun Sung

doi:10.1107/S1600536811040554

. 2011 Oct 8;67(Pt 11):o2865. doi: 10.1107/S1600536811040554

N-(4-Hydroxyphenyl)-3,4,5-trimethoxybenzamide

Hyeong Choi ^a, Yong Suk Shim ^a, Byung Hee Han ^a, Sung Kwon Kang ^a,^*, Chang Keun Sung ^b

PMCID: PMC3247600 PMID: 22219905

Abstract

In the title amide compound, C₁₆H₁₇NO₅, the dihedral angle between the benzene rings is 71.59 (4)°. In the crystal, intermolecular N—H⋯O and O—H⋯O hydrogen bonds link the molecules into a two-dimensional array parallel to the ab plane.

Related literature

For general background to tyrosinase and melanin, see: Kubo et al. (2000 ▶); Nerya et al. (2004 ▶). For the development of potent inhibitory agents of tyrosinase, see: Cabanes et al. (1994 ▶); Casanola-Martin et al. (2006 ▶); Thanigaimalai et al. (2010 ▶).

Experimental

Crystal data

C₁₆H₁₇NO₅
M _r = 303.31
Orthorhombic,
a = 10.4280 (5) Å
b = 13.4075 (6) Å
c = 21.5565 (8) Å
V = 3013.9 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.1 mm⁻¹
T = 296 K
0.23 × 0.16 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
14730 measured reflections
3459 independent reflections
2086 reflections with I > 2σ(I)
R _int = 0.130

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.134
S = 0.97
3459 reflections
207 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811040554/is2785sup1.cif

e-67-o2865-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040554/is2785Isup2.hkl

e-67-o2865-Isup2.hkl^{(166.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811040554/is2785Isup3.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
N9—H9⋯O17ⁱ	0.87 (2)	2.18 (2)	3.029 (2)	165.8 (17)
O16—H16⋯O8ⁱⁱ	0.88 (4)	1.84 (4)	2.710 (2)	172 (3)

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

Acknowledgments

We wish to thank the DBIO company for partial support of this work.

supplementary crystallographic information

Comment

Tyrosinase, a multi functional copper containing enzyme, is widely distributed in the plant and animal kingdom. It is responsible for catalyzing ortho-hydroxylation of phenols and ortho-phenol oxidation to corresponding quinones (Kubo et al., 2000). This enzyme was not only responsible for the browning of fruits and vegetables but also caused some dermatological problems such as flecks and melasma due to overproduction of melanin (Nerya et al., 2004). Numerous potential tyrosinase inhibitors have been discovered from natural and synthetic sources, such as a kojic acid (Cabanes et al., 1994), arbutin (Casanola-Martin et al., 2006) and phenylthiourea (Thanigaimalai et al., 2010). But some these inhibitors suffer from number of limitations, such as low activity and high toxicity. we have synthesized the title compound, (I), from the reaction of 3,4,5-trimethoxybenzoyl chloride and 4-aminophenol under ambient conditions. Herein, the crystal structure of (I) is described (Fig. 1).

The 3,4,5-trimethoxybenzoic acid moiety and 4-aminophenol group are essentially planar, with a mean deviation of 0.031 and 0.036 Å, respectively, from the corresponding least-squares plane defined by the ten and eight, respectively, constituent atoms. The dihedral angle between the benzene rings is 71.59 (4)°. The intermolecular N9—H9···O17ⁱ and O16—H16···O8ⁱⁱ [symmetry codes: (i) -x + 1/2, y - 1/2, z; (ii) -x - 1/2, y - 1/2, z; Table 1] hydrogen bonds allow to form an extensive two-dimensional network parallel to the ab plane (Fig. 2), which stabilizes the crystal structure.

Experimental

The 3,4,5-trimethoxybenzoyl chloride and 4-aminophenol were purchased from Sigma Chemical Co. Solvents for organic synthesis were redistilled before use. All other chemicals and solvents were of analytical grade and were used without further purification. The title compound was prepared from the reaction of 3,4,5-trimethoxybenzoyl chloride (0.5 g, 1.0 mmol) and 4-aminophenol (0.4 g, 1.2 mmol) by simple substitution in THF(6 ml) with triethylamine (0.22 g, 1.2 mmol). The solvent was removed under reduced pressure. The mixture compound were purified by column chromatography on silica gel (2:1 dichloromethane/ethylacetate) to give the title compound (69%, m.p. 504 K). Colourless crystals of (I) were obtained from its ethanolic solution by slow evaporation of the solvent at room temperature.