5-Benzylidenehydantoin Chemical Properties

Melting point:

220.00°C - 222.00°C

Density 

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

5-Benzylidenehydantoin Usage And Synthesis

Description

Derivatives 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].

Biological Activity

5-Benzylidenehydantoins inhibited the EGFR kinase and exhibited an antiproliferative action on A431 human epidermoid carcinoma cells. The conjugated exo-cyclic double bond at the C5 position appeared essential for both EGFR and cell growth inhibition, indicating that the 5-benzylidene hydantoin core would be a suitable scaffold for generating new antiproliferative compounds[3].

References

[1] Haq, K. U. et al. “Synthesis of 5-benzylidene-hydantoin and 5-benzylidene-creatinine derivatives under mixed catalyst systems of urea-p-toluenesulfonic acid (Urea-PTSA) and guanidine hydrochloride-triethylamine (GnHCl-TEA).”(2020).
[2] Andrea Cavazzoni. “Dual mechanisms of action of the 5-benzylidene-hydantoin UPR1024 on lung cancer cell lines.” Molecular Cancer Therapeutics 7 2 (2008): 361–70.

5-Benzylidenehydantoin(3775-01-7)Related Product Information

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