| Identification | Back Directory | [Name]
5-Benzylidenehydantoin | [CAS]
3775-01-7 | [Synonyms]
TIMTEC-BB SBB007867
RARECHEM AP KH 0029
Benzylidene hydantoin
5-Benzylidendhydantoin
5-BENZYLIDENEHYDANTOIN
5-phenylmethylenehydantoin
5-Benzylidene-2,4-imidazolidinedione
5-Benzylideneimidazolidine-2,4-dione
(5E)-5-Benzylidene-2,4-imidazolidinedione
2,4-Imidazolidinedione, 5-(phenylmethylene)-
5-BENZYLIDENEHYDANTOIN ---YELLOWISH POWDER--- | [Molecular Formula]
C10H8N2O2 | [MDL Number]
MFCD00014494 | [MOL File]
3775-01-7.mol | [Molecular Weight]
188.18 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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.
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