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Merck
CN

D214256

5,5-Diphenyl-2-thiohydantoin

99%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C15H12N2OS
CAS Number:
21083-47-6
Molecular Weight:
268.33
NACRES:
NA.22
PubChem Substance ID:
24893640
UNSPSC Code:
12352100
EC Number:
244-201-3
MDL number:
MFCD00005278
Assay:
99%
Form:
powder

Key Documents

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InChI key

AMDPNECWKZZEBQ-UHFFFAOYSA-N

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)

SMILES string

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

assay

99%

form

powder

mp

237-239 °C (lit.)

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
15613TE
S38253

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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
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
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
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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