1251738-89-2

Basic information

• Product Name: 2-cyclohexyl-4H-benzo[h]chromen-4-one
• Synonyms: 2-cyclohexyl-4H-benzo[h]chromen-4-one
• CAS NO: 1251738-89-2
• Molecular Weight: 278.351
• Mol File: 1251738-89-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-cyclohexyl-4H-benzo[h]chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-cyclohexyl-4H-benzo[h]chromen-4-one(1251738-89-2)
• EPA Substance Registry System: 2-cyclohexyl-4H-benzo[h]chromen-4-one(1251738-89-2)

Safety Data

• Hazardous Substances Data: 1251738-89-2(Hazardous Substances Data)

Upstream product

• 711-79-5 1-hydroxy-2-acetonaphthone 
• 3528-23-2 4H-benzo[h]chromen-4-one 
• 110-82-7 cyclohexane 

Relevant articles and documents

Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone

Selective cytochrome P450 (CYP) 1B1 inhibition has potential as an anticancer strategy that is unrepresented in the current clinical arena. For development of a selective inhibitor, we focused on the complexity caused by sp3-hybridized carbons and synthesized a series of benzo[h]chromone derivatives linked to a non-aromatic B-ring using α-naphthoflavone (ANF) as the lead compound. Ring structure comparison suggested compound 37 as a suitable cyclohexyl-core with improved solubility. Structural evolution of 37 produced the azide-containing cis-49a, which had good properties in three important respects: (1) selectivity for CYP1B1 over CYP1A1 and CYP1A2 (120-times and 150-times, respectively), (2) greater inhibitory potency of >2 times that of ANF, and (3) improved solubility. The corresponding aromatic B-ring compound 59a showed low selectivity and poor solubility. To elucidate the binding mode, we performed X-ray crystal structure analysis, which revealed the interaction mode and explained the subtype selectivity of cis-49a.

New synthetic flavone derivatives induce apoptosis of hepatocarcinoma cells

Natural flavonoids have broad biological activity, including anticancer. In this study, a series of novel flavone derivatives were synthesized with the substitutions of chlorine, isopropyl, methoxy, and nitro groups on the benzene ring of flavone skeleton to develop effective anticancer agents. Antiproliferative assays showed that the synthesized chemicals possess notable activity against hepatocarcinoma cells (HepG-2); in particular, the compound 6f with chlorine and dimethoxy modifications at the two benzene rings showed an IC50 at 1.1 μM to HepG-2. The 6f also displayed marked anticancer activity towards a panel of cancer cells, including nasopharyngeal carcinoma cells (CNE-2 and CNE-1), breast adenocarcinoma cell (MCF-7), and epithelial carcinoma cells (Hela). Exposing HepG-2 cells to compound 6f at 10 μM induced chromatin condensation, nuclear disassembly, and DNA fragmentation. In 6f-treated HepG-2 cells, the sub-G0 population was remarkably increased; and in these cells, both caspase-8 and caspase-9 activity was significantly increased, which in turn activated caspase-3. In addition, proapoptotic Bax was upregulated by compound 6f while the antiapoptotic Bcl-2 was downregulated. Taken together, our data suggest that the new flavonoid derivative 6f triggers apoptosis through both death-receptor and mitochondria-dependent intrinsic pathways, being a potent therapeutic agent against hepatocarcinoma.