243984-25-0

Basic information

• Product Name: 2-(ethoxycarbonyl)cyclohex-1-ene-1-sulfonic acid
• Synonyms: 2-(ethoxycarbonyl)cyclohex-1-ene-1-sulfonic acid
• CAS NO: 243984-25-0
• Molecular Weight: 234.273
• Mol File: 243984-25-0.mol

Chemical Properties

• CAS DataBase Reference: 2-(ethoxycarbonyl)cyclohex-1-ene-1-sulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(ethoxycarbonyl)cyclohex-1-ene-1-sulfonic acid(243984-25-0)
• EPA Substance Registry System: 2-(ethoxycarbonyl)cyclohex-1-ene-1-sulfonic acid(243984-25-0)

Safety Data

• Hazardous Substances Data: 243984-25-0(Hazardous Substances Data)

Upstream product

• 54928-91-5 ethyl 2-mercaptocyclohex-1-ene-1-carboxylate 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 

Downstream Products

• 243984-26-1 ethyl 2-(chlorosulfonyl)cyclohex-1-ene-1-carboxylate 
• 243983-44-0 d-ethyl 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate 
• 243983-42-8 ethyl 6-[N-(4-chloro-2-fluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate 
• 243984-11-4 ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate 
• 243984-10-3 ethyl (6S)-6-[N-(2-chloro-4-fluoro-phenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate 
• 243983-70-2 ethyl (6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate 

Relevant articles and documents

Synthesis and rational design of anti-inflammatory compounds: N-phenyl-cyclohexenyl sulfonamide derivatives

The synthesis of (±)-ethyl 6-[N-(2-chloro-4-fluorophenyl)sulfamoyl] cyclohex-1-ene-1-carboxylate (5n) has been reproduced from a method previously described and served as the background for the preparation of a nitro derivative, potentially useful as an a

Discovery of novel and potent small-molecule inhibitors of NO and cytokine production as antisepsis agents: Synthesis and biological activity of alkyl 6-(N-substituted sulfamoyl)cyclohex-1-ene-1-carboxylate

To develop a new therapeutic agent for sepsis, screening of the Takeda chemical library was carried out using mouse macrophages stimulated with lipopolysaccharide (LPS) to identify a new class of small-molecule inhibitors of inflammatory mediator production. The lead compound 5a was discovered, from which a series of novel cyclohexene derivatives I bearing a sulfamoyl and ester group were designed, synthesized and tested for their inhibitory activity against nitric oxide (NO) production. Derivatives I were synthesized by the coupling of sulfonyl chlorides and anilines with concomitant double bond migration in the presence of triethylamine, and phenyl ring substitution and modification of the ester and cyclohexene moieties were carried out. Among the compounds synthesized, ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]- cyclohex-1-ene-1-carboxylate [(R)-(+)-5n, TAK-242] was found to exhibit the most potent suppressive activity for the production of not only NO but also inflammatory cytokines, such as tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) induced by LPS-stimulated mouse macrophages with IC 50 values of 1.8, 1.9 and 1.3 nM, respectively. It shows marked beneficial effects in vivo also. Intravenous administration of (R)-(+)-5n at doses of 0.1 mg/kg or more suppressed the production of NO and various cytokines [TNF-α, IL-6 and IL-1β] in the mouse endotoxin shock model. Furthermore, it protected mice from death dose-dependently and all mice survived at a dose of 3 mg/kg. The minimum effective dose to protect mice from lethality in this model was 0.3 mg/kg, which was consistent with those for inhibitory effects on the production of NO and cytokines. Compound CR)-(+)-5n is currently undergoing clinical trials for the treatment of sepsis.

Cycloalkene derivatives, process for producing the same, and use

The present invention provides a compound represented by the formula: wherein R represents an aliphatic hydrocarbon group optionally having substituents, an aromatic hydrocarbon group optionally having substituents, a heterocyclic group optionally having