109402-17-7

Basic information

• Product Name: 6,7,8,9-TETRAHYDRO-2''H,5''H-SPIRO[BENZO[7]ANNULENE-5,4''-IMIDAZOLIDINE]-2'',5''-DIONE
• Synonyms: 6,7,8,9-TETRAHYDRO-2H,5H-SPIRO[BENZO[7]ANNULENE-5,4-IMIDAZOLIDINE]-2,5-DIONE(WX145596)
• CAS NO: 109402-17-7
• Molecular Formula: C13H14N2O2
• Molecular Weight: 230.266
• Mol File: 109402-17-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.3g/cm³
• CAS DataBase Reference: 6,7,8,9-TETRAHYDRO-2''H,5''H-SPIRO[BENZO[7]ANNULENE-5,4''-IMIDAZOLIDINE]-2'',5''-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7,8,9-TETRAHYDRO-2''H,5''H-SPIRO[BENZO[7]ANNULENE-5,4''-IMIDAZOLIDINE]-2'',5''-DIONE(109402-17-7)
• EPA Substance Registry System: 6,7,8,9-TETRAHYDRO-2''H,5''H-SPIRO[BENZO[7]ANNULENE-5,4''-IMIDAZOLIDINE]-2'',5''-DIONE(109402-17-7)

Safety Data

• Hazardous Substances Data: 109402-17-7(Hazardous Substances Data)

Upstream product

• 151-50-8 potassium cyanide 
• 826-73-3 1-Benzosuberone 
• 57-12-5 cyanide^(1-) 
• 506-87-6 ammonium carbonate 

Relevant articles and documents

Scaffold hybridization strategy towards potent hydroxamate-based inhibitors of: Flaviviridae viruses and Trypanosoma species

Infections with Flaviviridae viruses, such as hepatitis C virus (HCV) and dengue virus (DENV) pose global health threats. Infected individuals are at risk of developing chronic liver failure or haemorrhagic fever respectively, often with a fatal outcome if left untreated. Diseases caused by tropical parasites of the Trypanosoma species, T. brucei and T. cruzi, constitute significant socioeconomic burden in sub-Saharan Africa and continental Latin America, yet drug development is under-funded. Anti-HCV chemotherapy is associated with severe side effects and high cost, while dengue has no clinically approved therapy and antiparasitic drugs are outdated and difficult to administer. Moreover, drug resistance is an emerging concern. Consequently, the need for new revolutionary chemotherapies is urgent. By utilizing a molecular framework combination approach, we combined two distinct chemical entities with proven antiviral and trypanocidal activity into a novel hybrid scaffold attached by an acetohydroxamic acid group (CH2CONHOH), aiming at derivatives with dual activity. The novel spiro-carbocyclic substituted hydantoin analogues were rationally designed, synthesized and evaluated for their potency against three HCV genotypes (1b, 3a, 4a), DENV and two Trypanosoma species (T. brucei, T. cruzi). They exhibited significant EC50 values and remarkable selectivity indices. Several modifications were undertaken to further explore the structure activity relationships (SARs) and confirm the pivotal role of the acetohydroxamic acid metal binding group.

Spiro hydantoin aldose reductase inhibitors

Sorbitol formation from glucose, catalyzed by the enzyme aldose reductase, is believed to play a role in the development of certain chronic complications of diabetes mellitus. Spiro hydantoin derived from five- and six-membered ketones fused to an aromatic ring or ring system inhibit aldose reductase isolated from calf lens. In vivo these compounds are potent inhibitors of sorbitol formation in sciatic nerves of streptozotocinized rats. Optimum in vivo activity is reached in spiro hydantoins derived from 6-halogenated 2,3-dihydro-4H-1-benzopyran-4-ones (4-chromanones). In 2,4-dihydro-6-fluorospirol[4H-1-benzopyran-4,4'-imidazolidine]-2',5'- ione, the activity resides exclusively in the 4S isomer, compound 115 (CP-45,634, USAN: sorbinil). This compound is currently being used to test, in humans, the value of aldose reductase inhibitors in the therapy of diabetic complications.