Literature DB >> 22347126

1-(3-Hy-droxy-phen-yl)-3-(3-meth-oxy-phenyl)thio-urea.

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

Abstract

In the title compound, C(14)H(14)N(2)O(2)S, the dihedral angles between the thio-urea group and the methoxyphenyl and hydroxyphenyl rings are 61.91 (4) and 76.90 (4)°, respectively. The benzene rings are twisted with respect to each other, making a dihedral angle of 71.03 (4)°. The H atoms of the thio-urea NH groups are positioned anti to each other. In the crystal, inter-molecular N-H⋯S, N-H⋯O and O-H⋯S hydrogen bonds link the mol-ecules into a three-dimensional network.

Entities: CellLine Chemical Disease Species

Year: 2012 PMID： 22347126 PMCID： PMC3275270 DOI： 10.1107/S1600536812002553

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For general background to tyrosinase, see: Kubo et al. (2000 ▶). For the development of tyrosinase inhibitors, see: Son et al. (2000 ▶); Iida et al. (1995 ▶); Kojima et al. (1995 ▶); Cabanes et al. (1994 ▶).

Experimental

Crystal data

C14H14N2O2S M = 274.33 Triclinic, a = 6.9925 (4) Å b = 9.8666 (6) Å c = 10.4238 (6) Å α = 103.055 (2)° β = 100.033 (1)° γ = 90.508 (1)° V = 688.99 (7) Å3 Z = 2 Mo Kα radiation μ = 0.23 mm−1 T = 296 K 0.2 × 0.17 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.956, T max = 0.975 26807 measured reflections 3419 independent reflections 2503 reflections with I > 2σ(I) R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.097 S = 1.01 3419 reflections 184 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.18 e Å−3 Δρmin = −0.20 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002553/bh2409sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002553/bh2409Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812002553/bh2409Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₄N₂O₂S	Z = 2
M_r = 274.33	F(000) = 288
Triclinic, P1	D_x = 1.322 Mg m⁻³
Hall symbol: -P 1	Melting point: 401 K
a = 6.9925 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8666 (6) Å	Cell parameters from 5768 reflections
c = 10.4238 (6) Å	θ = 2.6–27.4°
α = 103.055 (2)°	µ = 0.23 mm⁻¹
β = 100.033 (1)°	T = 296 K
γ = 90.508 (1)°	Block, colourless
V = 688.99 (7) Å³	0.2 × 0.17 × 0.08 mm

Bruker SMART CCD area-detector diffractometer	2503 reflections with I > 2σ(I)
graphite	R_int = 0.046
φ and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
T_min = 0.956, T_max = 0.975	k = −13→13
26807 measured reflections	l = −13→13
3419 independent reflections

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0503P)²] where P = (F_o² + 2F_c²)/3
3419 reflections	(Δ/σ)_max < 0.001
184 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³
0 constraints

	x	y	z	U_iso*/U_eq
C1	0.24836 (18)	0.58574 (16)	0.14956 (13)	0.0403 (3)
H1	0.2357	0.6671	0.2123	0.048*
C2	0.23577 (19)	0.58682 (17)	0.01519 (14)	0.0438 (4)
C3	0.2516 (2)	0.46570 (19)	−0.07750 (15)	0.0501 (4)
H3	0.2405	0.4666	−0.1675	0.06*
C4	0.2838 (2)	0.34340 (19)	−0.03709 (16)	0.0544 (4)
H4	0.2945	0.2617	−0.1001	0.065*
C5	0.3005 (2)	0.34057 (17)	0.09647 (16)	0.0491 (4)
H5	0.3253	0.258	0.1239	0.059*
C6	0.28010 (19)	0.46141 (16)	0.18824 (13)	0.0395 (3)
N7	0.29788 (18)	0.46161 (13)	0.32718 (12)	0.0439 (3)
H7	0.387 (2)	0.5124 (16)	0.3796 (16)	0.053 (5)*
C8	0.19730 (19)	0.37739 (14)	0.37909 (13)	0.0359 (3)
S9	0.26879 (6)	0.36711 (4)	0.53992 (4)	0.04690 (14)
N10	0.04156 (17)	0.30682 (13)	0.29859 (12)	0.0412 (3)
H10	0.007 (2)	0.3295 (17)	0.2288 (16)	0.050 (5)*
C11	−0.07082 (19)	0.19821 (14)	0.32679 (13)	0.0376 (3)
C12	0.0066 (2)	0.07050 (14)	0.32391 (13)	0.0397 (3)
H12	0.1324	0.0564	0.3077	0.048*
C13	−0.1033 (2)	−0.03815 (15)	0.34530 (13)	0.0407 (3)
C14	−0.2904 (2)	−0.01681 (17)	0.36628 (16)	0.0530 (4)
H14	−0.366	−0.0894	0.3783	0.064*
C15	−0.3659 (2)	0.11175 (19)	0.3695 (2)	0.0643 (5)
H15	−0.4917	0.1257	0.3858	0.077*
C16	−0.2575 (2)	0.22180 (17)	0.34868 (17)	0.0542 (4)
H16	−0.3097	0.3083	0.3496	0.065*
O17	0.20472 (17)	0.70305 (13)	−0.03543 (11)	0.0593 (3)
C18	0.2042 (3)	0.8340 (2)	0.0567 (2)	0.0800 (6)
H18A	0.1815	0.9061	0.0082	0.12*
H18B	0.3277	0.8528	0.116	0.12*
H18C	0.1031	0.8313	0.1078	0.12*
O19	−0.01696 (17)	−0.16246 (11)	0.34188 (11)	0.0543 (3)
H19	−0.080 (3)	−0.213 (3)	0.385 (2)	0.110 (8)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0375 (7)	0.0498 (9)	0.0336 (7)	−0.0083 (6)	0.0027 (6)	0.0126 (6)
C2	0.0341 (7)	0.0620 (10)	0.0381 (8)	−0.0061 (6)	0.0013 (6)	0.0216 (7)
C3	0.0393 (8)	0.0787 (12)	0.0317 (8)	−0.0072 (7)	0.0041 (6)	0.0136 (8)
C4	0.0491 (9)	0.0648 (11)	0.0425 (9)	−0.0062 (8)	0.0096 (7)	−0.0022 (8)
C5	0.0487 (8)	0.0509 (9)	0.0470 (9)	−0.0063 (7)	0.0066 (7)	0.0121 (8)
C6	0.0344 (7)	0.0515 (9)	0.0319 (7)	−0.0131 (6)	0.0010 (5)	0.0127 (6)
N7	0.0487 (7)	0.0492 (8)	0.0318 (6)	−0.0212 (6)	−0.0042 (5)	0.0148 (6)
C8	0.0411 (7)	0.0333 (7)	0.0328 (7)	−0.0049 (6)	0.0015 (6)	0.0108 (6)
S9	0.0577 (2)	0.0490 (2)	0.0323 (2)	−0.02053 (17)	−0.00393 (16)	0.01601 (16)
N10	0.0430 (6)	0.0451 (7)	0.0356 (7)	−0.0136 (5)	−0.0051 (5)	0.0197 (6)
C11	0.0402 (7)	0.0392 (8)	0.0317 (7)	−0.0112 (6)	−0.0015 (6)	0.0116 (6)
C12	0.0420 (7)	0.0418 (8)	0.0348 (7)	−0.0067 (6)	0.0060 (6)	0.0092 (6)
C13	0.0525 (8)	0.0371 (8)	0.0303 (7)	−0.0087 (6)	0.0023 (6)	0.0077 (6)
C14	0.0492 (9)	0.0516 (10)	0.0594 (10)	−0.0168 (7)	0.0060 (7)	0.0193 (8)
C15	0.0391 (8)	0.0711 (12)	0.0908 (14)	−0.0043 (8)	0.0140 (8)	0.0339 (11)
C16	0.0448 (8)	0.0510 (10)	0.0710 (11)	0.0011 (7)	0.0076 (8)	0.0249 (8)
O17	0.0678 (7)	0.0717 (8)	0.0435 (6)	0.0008 (6)	0.0024 (5)	0.0301 (6)
C18	0.1086 (16)	0.0616 (13)	0.0721 (14)	−0.0002 (11)	0.0033 (12)	0.0304 (11)
O19	0.0752 (8)	0.0382 (6)	0.0528 (7)	−0.0032 (5)	0.0191 (6)	0.0121 (5)

C1—C6	1.3834 (19)	N10—H10	0.807 (16)
C1—C2	1.3904 (18)	C11—C12	1.3721 (19)
C1—H1	0.93	C11—C16	1.376 (2)
C2—O17	1.3706 (18)	C12—C13	1.3938 (18)
C2—C3	1.376 (2)	C12—H12	0.93
C3—C4	1.373 (2)	C13—O19	1.3677 (17)
C3—H3	0.93	C13—C14	1.374 (2)
C4—C5	1.383 (2)	C14—C15	1.374 (2)
C4—H4	0.93	C14—H14	0.93
C5—C6	1.376 (2)	C15—C16	1.397 (2)
C5—H5	0.93	C15—H15	0.93
C6—N7	1.4314 (17)	C16—H16	0.93
N7—C8	1.3429 (17)	O17—C18	1.425 (2)
N7—H7	0.832 (16)	C18—H18A	0.96
C8—N10	1.3338 (16)	C18—H18B	0.96
C8—S9	1.6900 (13)	C18—H18C	0.96
N10—C11	1.4353 (16)	O19—H19	0.90 (2)

C6—C1—C2	118.81 (14)	C12—C11—C16	121.41 (13)
C6—C1—H1	120.6	C12—C11—N10	119.07 (12)
C2—C1—H1	120.6	C16—C11—N10	119.42 (13)
O17—C2—C3	115.33 (13)	C11—C12—C13	119.98 (13)
O17—C2—C1	124.32 (15)	C11—C12—H12	120
C3—C2—C1	120.35 (14)	C13—C12—H12	120
C4—C3—C2	119.98 (14)	O19—C13—C14	123.60 (13)
C4—C3—H3	120	O19—C13—C12	117.00 (13)
C2—C3—H3	120	C14—C13—C12	119.40 (14)
C3—C4—C5	120.59 (15)	C15—C14—C13	120.02 (14)
C3—C4—H4	119.7	C15—C14—H14	120
C5—C4—H4	119.7	C13—C14—H14	120
C6—C5—C4	119.14 (15)	C14—C15—C16	121.26 (15)
C6—C5—H5	120.4	C14—C15—H15	119.4
C4—C5—H5	120.4	C16—C15—H15	119.4
C5—C6—C1	121.10 (13)	C11—C16—C15	117.91 (15)
C5—C6—N7	120.30 (14)	C11—C16—H16	121
C1—C6—N7	118.56 (13)	C15—C16—H16	121
C8—N7—C6	126.11 (12)	C2—O17—C18	118.09 (13)
C8—N7—H7	116.8 (11)	O17—C18—H18A	109.5
C6—N7—H7	116.7 (11)	O17—C18—H18B	109.5
N10—C8—N7	116.72 (12)	H18A—C18—H18B	109.5
N10—C8—S9	123.46 (10)	O17—C18—H18C	109.5
N7—C8—S9	119.81 (10)	H18A—C18—H18C	109.5
C8—N10—C11	125.96 (12)	H18B—C18—H18C	109.5
C8—N10—H10	116.2 (11)	C13—O19—H19	108.9 (15)
C11—N10—H10	117.9 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···S9ⁱ	0.832 (16)	2.588 (16)	3.3683 (12)	156.8 (14)
N10—H10···O17ⁱⁱ	0.807 (16)	2.239 (16)	2.9547 (16)	148.0 (15)
O19—H19···S9ⁱⁱⁱ	0.90 (2)	2.35 (3)	3.2424 (12)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯S9ⁱ	0.832 (16)	2.588 (16)	3.3683 (12)	156.8 (14)
N10—H10⋯O17ⁱⁱ	0.807 (16)	2.239 (16)	2.9547 (16)	148.0 (15)
O19—H19⋯S9ⁱⁱⁱ	0.90 (2)	2.35 (3)	3.2424 (12)	170 (2)

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

6 in total

6. Inhibitory effect of sodium 5,6-benzylidene ascorbate (SBA) on the elevation of melanin biosynthesis induced by ultraviolet-A (UV-A) light in cultured B-16 melanoma cells.

Authors: S Kojima; H Yamaguchi; K Morita; Y Ueno
Journal: Biol Pharm Bull Date: 1995-08 Impact factor: 2.233

6 in total

1-(3-Hy-droxy-phen-yl)-3-(3-meth-oxy-phenyl)thio-urea.

Related literature

Experimental

Crystal data

Data collection

Refinement

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5. Kojic acid, a cosmetic skin whitening agent, is a slow-binding inhibitor of catecholase activity of tyrosinase.

6. Inhibitory effect of sodium 5,6-benzylidene ascorbate (SBA) on the elevation of melanin biosynthesis induced by ultraviolet-A (UV-A) light in cultured B-16 melanoma cells.