15945-75-2

Usage

Uses

Used in Organic Synthesis:
2-Chloro-5-methylsulfanyl-phenylamine is used as a building block in organic synthesis for its ability to contribute to the formation of a variety of organic compounds. Its presence in the molecular structure allows for the creation of diverse chemical entities with potential applications across different industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-chloro-5-methylsulfanyl-phenylamine is utilized as a key intermediate in the development of new drugs. Its unique properties and reactivity make it a valuable component in the synthesis of pharmaceuticals, potentially leading to the discovery of novel therapeutic agents.
Used in Chemical Production:
2-Chloro-5-methylsulfanyl-phenylamine is also used in the production of a wide range of chemical products. Its versatility in chemical reactions and compatibility with various organic solvents make it a valuable asset in the manufacturing process of different chemical entities.

Upstream product

• 1199-36-6 1-chloro-4-(methylthio)-2-nitrobenzene 
• 108-24-7 acetic anhydride 
• 51546-12-4 2-chloro-5-(methylthio)benzoic acid 

Downstream Products

• 342042-24-4 2-chloro-5-methanesulfinyl-phenyl-cyanamide 

Relevant academic research and scientific papers

N′-3-(Trifluoromethyl)phenyl Derivatives of N-Aryl-N′-methylguanidines as Prospective PET Radioligands for the Open Channel of the N-Methyl- d -aspartate (NMDA) Receptor: Synthesis and Structure-Affinity Relationships

N-Methyl-d-aspartate (NMDA) receptor dysfunction has been linked to several neuropsychiatric disorders, including Alzheimer's disease, epilepsy, drug addiction, and schizophrenia. A radioligand that could be used with PET to image and quantify human brain NMDA receptors in the activated "open channel" state would be useful for research on such disorders and for the development of novel therapies. To date, no radioligands have shown well-validated efficacy for imaging NMDA receptors in human subjects. In order to discover improved radioligands for PET imaging, we explored structure-affinity relationships in N′-3-(trifluoromethyl)phenyl derivatives of N-aryl-N′-methylguanidines, seeking high affinity and moderate lipophilicity, plus necessary amenability for labeling with a positron-emitter, either carbon-11 or fluorine-18. Among a diverse set of 80 prepared N′-3-(trifluoromethyl)phenyl derivatives, four of these compounds (13, 19, 20, and 36) displayed desirable low nanomolar affinity for inhibition of [3H](+)-MK801 at the PCP binding site and are of interest for candidate PET radioligand development.

Identification and characterization of a potential ischemia-selective N-methyl-D-aspartate (NMDA) receptor ion-channel blocker, CNS 5788

The identification and characterization of a potentially ischemia-selective and orally-active sulfoxide based NMDA ion-channel blocker showing good neuroprotective activity, (R)-(+)-N-(2-chloro-5-methylthiophenyl)-N′-(3-methylsulfinylphenyl)- N′-methylguanidine (CNS 5788), is described.

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.