5-Benzylidenehydantoin

HCID 97857

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Basic information

CAS: 3775-01-7
Standard SMILES: O=C1NC(=O)C(=Cc2ccccc2)N1
InChIKey: UDTSPKADQGPZFS-UHFFFAOYSA-N
Molecular formula: C10H8N2O2
Average molar mass: 188.18 g/mol

Names & identifiers

Preferred name: 5-Benzylidenehydantoin
IUPAC: 5-benzylideneimidazolidine-2,4-dione
English name: 5-Benzylidenehydantoin
Molecular formula: C10H8N2O2
Molecular weight: 188.18

Names & synonyms

5-Benzylidenehydantoin5-benzylideneimidazolidine-2,4-dione3775-01-7MLS002667257TimTec1_005370benzalhydantoin5-benzalhydantoinbenzylidene hydantoin5-benzylidene hydantoin5-benzylidene-hydantoinAspartate Impurity 105-benzylidene-hydantoine

Show more names

RARECHEM AP KH 0029TIMTEC-BB SBB0078675-Benzylidendhydantoin5-phenylmethylenehydantoin5-Benzylidene-2,4-imidazolidinedione(5E)-5-Benzylidene-2,4-imidazolidinedione2,4-Imidazolidinedione, 5-(phenylmethylene)-

hydroxybenzylidene imidazoloneSCHEMBL1358078SCHEMBL1984968SCHEMBL5145065SCHEMBL8010088CHEMBL1725125SCHEMBL11851323UDTSPKADQGPZFS-UHFFFAOYSA-N

Database identifiers

CAS: 3775-01-7
PubChem CID: 97857
ChEMBL: CHEMBL1725125
EC Number: 609-473-3

Properties

Computed structural properties

XLogP: 1.1
Topological polar surface area: 58.2 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 14
Formal charge: 0
Complexity: 290

Physicochemical properties

Melting point: 220 °C · 220.00°C - 222.00°C
Density: 1.329 g/cm3 · 1.329g/cm3
InChI: InChI=1S/C10H8N2O2/c13-9-8(11-10(14)12-9)6-7-4-2-1-3-5-7/h1-6H,(H2,11,12,13,14)
InChIKey: UDTSPKADQGPZFS-UHFFFAOYSA-N
SMILES: C1(=O)NC(=CC2=CC=CC=C2)C(=O)N1

Chemistry & industry

Applications · 1 item

DescriptionDerivatives of 5-Benzylidenehydantoin are well known of their various attractive bioactivities such as anticancer, antimicrobial, antidiabetic and tyrosinase inhibitor. UPR1024 belongs to a new class of EGFR inhibitors characterized by a hydantoin nucleus and a 5-benzylidene substituent having a double bond conjugated with a carbonyl group on the hydantoin ring. The compound had antiproliferative and proapoptotic effects when tested on the non-small cell lung cancer cell line A549[1-2].