156461-79-9

Usage

Uses

Used in Pharmaceutical Industry:
(3-Methanesulfonyl-phenyl)-methyl-amine is used as a building block for the production of various pharmaceuticals and agrochemicals. Its unique chemical structure allows it to be a versatile component in the synthesis of a wide range of compounds with potential therapeutic applications.
Used in Organic Synthesis:
(3-Methanesulfonyl-phenyl)-methyl-amine is used as a key intermediate in the synthesis of complex organic molecules. Its presence in the molecule can influence the reactivity and selectivity of the reactions, making it a valuable component in the development of new synthetic routes.
Used in Neurological Disorders Research:
(3-Methanesulfonyl-phenyl)-methyl-amine is used as a potential treatment for neurological disorders due to its pharmacological properties. Its role as a monoamine oxidase inhibitor suggests that it may have therapeutic potential in the treatment of conditions such as depression, anxiety, and Parkinson's disease.
Used in Monoamine Oxidase Inhibition:
(3-Methanesulfonyl-phenyl)-methyl-amine is used as a monoamine oxidase inhibitor, which can help regulate the levels of monoamines in the brain. This property makes it a promising candidate for the development of drugs targeting neurological disorders associated with monoamine imbalances.
Used in Precursor Synthesis:
(3-Methanesulfonyl-phenyl)-methyl-amine is used as a precursor in the synthesis of pharmaceutically active compounds. Its unique structure and reactivity make it a valuable starting material for the development of new drugs with improved efficacy and selectivity.

Upstream product

• 52960-99-3 N-methyl-3-methylthioaniline 
• 1783-81-9 3-methylmercaptoaniline 

Downstream Products

• 156461-84-6 3-methanesulfonyl-N-methylphenylnitramine 

Relevant academic research and scientific papers

Synthesis and pharmacological evaluation of N-(2,5-disubstituted phenyl)-N'-(3-substituted phenyl)-N'-methylguanidines as N-methyl-D-aspartate receptor ion-channel blockers

In the mammalian central nervous system, the N-methyl-D-aspartate (NMDA) subclass of glutamate receptors may play an important role in brain diseases such as stroke, brain or spinal cord trauma, epilepsy, and certain neurodegenerative diseases. Compounds which specifically antagonize the actions of the neurotransmitter glutamate at the NMDA receptor ion-channel site offer a novel approach to treating these disorders. CERESTAT (4, aptiganel CNS 1102) is currently undergoing clinical trial for the treatment of traumatic brain injury and stroke. Previously, we reported that analogues of N-1-naphthyl-N'-(3-ethylphenyl)-N'-methylguanidine (4) bound to the NMDA receptor ion-channel site with high potency and selectivity. Recently, molecules active at both σ receptors and NMDA receptor sites were investigated. A series of substituted diphenylguanidines 6 which are structurally related to N-1-naphthyl-N'-(3-ethylphenyl)-N'-methylguanidine was prepared. Compounds containing appropriate substitution/pattern in one of the phenyl rings of diphenylguanidines displayed high affinity. For example, N-(2,5-dibromophenyl)-N'-(3-ethylphenyl)-N'-methylguanidine (27b, R2 = R5 = Br, R3 = C2H5) exhibited potency at both 5 receptors and NMDA receptor sites; 27b also showed high efficacy in vivo in a neonatal rat excitotoxicity model. Further studies indicated that substituent effects were important in this compound series, and 2,5-disubstituted phenyl was the preferred substitution pattern for high-affinity binding at NMDA receptor sites. Bromo and methylthio were the optimal substituents for the R2 and R5 positions of the 2,5-disubstituted phenyl group, respectively. N-(2-Bromo-5- (methylthio)phenyl)-N'-(3-ethylphenyl)-N'-methylguanidine (34b, R2 = Br, R5 = SMe, R3 = C2H5) was highly active at NMDA receptor sites. We found that the binding affinity of guanidines of type 6 could be further enhanced with the appropriate substitution at R3. Optimal activity in this series are afforded by 43b and 44b (R2 = Cl or Br, R5 = R3 = SCH3). Both 43b and 44b bound to NMDA receptor sites with high potency and selectivity (K(i) vs [3H]MK-801: 1.87 and 1.65 nM, respectively); these compounds are active in vivo in various animal models of neuroprotection. The structure-activity relationships for these compounds at the NMDA receptor ion-channel site are discussed.