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D214256

Sigma-Aldrich

5,5-Diphenyl-2-thiohydantoin

99%

Sinónimos:

5,5-Diphenyl-2-thioxo-4-imidazolidinone, 5,5-Diphenylimidazolidine-4-one-2-thione, DPTH

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About This Item

Fórmula empírica (notación de Hill):
C15H12N2OS
Número de CAS:
21083-47-6
Peso molecular:
268.33
EC Number:
244-201-3
MDL number:
MFCD00005278
UNSPSC Code:
12352100
PubChem Substance ID:
24893640
NACRES:
NA.22

assay

99%

form

powder

mp

237-239 °C (lit.)

SMILES string

O=C1NC(=S)NC1(c2ccccc2)c3ccccc3

InChI

1S/C15H12N2OS/c18-13-15(17-14(19)16-13,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,16,17,18,19)

InChI key

AMDPNECWKZZEBQ-UHFFFAOYSA-N

Gene Information

human ... CNR1(1268) , CNR2(1269)
rat ... Faah(29347)

Application

Reactant for synthesis of:
  • Imidazole derivatives
  • Imidazothiazole and glycocyamidine derivatives for antimicrobial studies
  • Fatty acid amide hydrolase inhibitor templates
  • Anti-cancer agents
  • Hydantoins and thiohydantoins
  • Acyl CoA: cholesterol acyltransferase inhibitors

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
15613TE
S38253

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H Gerber et al.
Endocrinology, 135(6), 2688-2699 (1994-12-01)
Some years ago, we reported that colloid goiters could be produced experimentally in mice and rats by injection of TSH over a few days in the presence of ample iodine supply. This clearly showed that colloid accumulation and intense TSH
Yuan Liu et al.
Cancer letters, 271(2), 294-305 (2008-07-25)
Previously, we demonstrated that 5,5-diphenyl-2-thiohydantoin (DPTH) exerts an anti-proliferation effect on subcultured human umbilical vein endothelial cells (HUVEC). In the present study, we show that 2(naphthalen-2-ylmethylsulfanyl)-5,5-diphenyl-1,5-dihydro-imidazol-4-one (DPTH-N10), a derivative compound of DPTH, exerts a 5 times stronger inhibition of [3H]thymidine
Hitoshi Yoshino et al.
Bioorganic & medicinal chemistry, 18(23), 8150-8157 (2010-11-06)
A series of 5,5-dimethylthiohydantoin derivatives were synthesized and evaluated for androgen receptor pure antagonistic activities for the treatment of castration-resistant prostate cancer. Since CH4933468, which we reported previously, had a problem with agonist metabolites, novel thiohydantoin derivatives were identified by
Cheng-Kuo Cheng et al.
Vascular pharmacology, 48(2-3), 138-142 (2008-02-26)
Previously, we identified DPTH, an analogue of antiepileptic drug phenytoin (5,5-diphenylhydantoin, DPT), capable of retarding the cell cycle in the human vascular endothelial cells. Our data suggest that DPTH inhibits human umbilical venous endothelial cells (HUVEC) proliferation by increasing the
Naimeh Moshtael Arani et al.
Ultrasonics sonochemistry, 18(2), 640-643 (2010-10-06)
To obtain a rapid, efficient and mild synthesis of 5,5-diphenylhydantoin and 5,5-diphenyl-2-thiohydantoin derivatives, ultrasonic irradiation has been applied to the reaction mixtures containing substituted benzils and urea or thiourea derivatives catalyzed by KOH in DMSO/H(2)O, which allowed us to achieve
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