306935-59-1

Basic information

• Product Name: 5-NITROSPIRO[BENZIMIDAZOLE-2,1'-CYCLOPENTANE] 1,3-DIOXIDE
• Synonyms: 5-NITROSPIRO[BENZIMIDAZOLE-2,1'-CYCLOPENTANE] 1,3-DIOXIDE;5-NITRO-2-SPIROCYCLOPENTANE-2H-BENZIMIDAZOLE-1 3-DIOXIDE;5-nitro-2-spirocyclopentane-2H-benzimidazol-1,3-dioxide;5-Nitro-spiro[benzoimidazole-2,1'-cyclopentane] 1,3-dioxide
• CAS NO: 306935-59-1
• Molecular Formula: C11H11N3O4
• Molecular Weight: 249.22
• Mol File: 306935-59-1.mol

Chemical Properties

• Melting Point: 148-150
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• PKA: -6.03±0.20(Predicted)
• CAS DataBase Reference: 5-NITROSPIRO[BENZIMIDAZOLE-2,1'-CYCLOPENTANE] 1,3-DIOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NITROSPIRO[BENZIMIDAZOLE-2,1'-CYCLOPENTANE] 1,3-DIOXIDE(306935-59-1)
• EPA Substance Registry System: 5-NITROSPIRO[BENZIMIDAZOLE-2,1'-CYCLOPENTANE] 1,3-DIOXIDE(306935-59-1)

Safety Data

• Hazard Codes: Xi
• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 306935-59-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H11N3O4/c15-12-9-4-3-8(14(17)18)7-10(9)13(16)11(12)5-1-2-6-11/h3-4,7H,1-2,5-6H2

Upstream product

• 96-41-3 Cyclopentanol 
• 3702-88-3 5-nitrobenzofuroxane 
• 14208-17-4 o-benzoquinone-1,2-dioxime 
• 120-92-3 cyclopentanone 
• 38629-55-9 spiro(2H-benzimidazole-2-cyclopentane) 1,3-dioxide 

Relevant articles and documents

Synthesis of 2H-benzimidazole 1,3-dioxides, separase inhibitors, by reaction of o-benzoquinone dioximes with ketones

The synthesis of novel 2H-benzimidazole 1,3-dioxides on the basis of o-benzoquinone dioximes interaction with ketones in the presence of acids is described. Nitration of these compounds by nitric acid in acetic acid yields the 5-nitro derivatives of 2H-benzimidazole 1,3-dioxide.

Synthesis and activity of benzimidazole-1,3-dioxide inhibitors of separase

Due to the oncogenic activity of cohesin protease, separase in human cancer cells, modulation of separase enzymatic activity could constitute a new therapeutic strategy for targeting resistant, separase-overexpressing aneuploid tumors. Herein, we report the synthesis, structural information, and structure–activity relationship (SAR) of separase inhibitors based on modification of the lead molecule 2,2-dimethyl-5-nitro-2H-benzimidazole-1,3-dioxide, named Sepin-1, (1) identified from a high-throughput-screen. Replacement of –NO2at C5 with other functional groups reduce the inhibitory activity in separase enzymatic assay. Substitution of the two methyl groups with other alkyl chains at the C2 moderately improves the effects on the inhibitory activity of those compounds. Modifications on 2H-benzimidazole-1,3-dioxide or the skeleton have variable effect on inhibition of separase enzymatic activity. Density-functional theory (DFT) calculations suggest there may be a correlation between the charges on the oxide moieties on these compounds and their activity in inhibiting separase enzyme.