Production Method 1

21436-03-3

953805-46-4

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  cooled; heated; overnight, rt

Reference

Asymmetric Synthesis of Polysubstituted 4-Amino- and 3,4-Diaminochromanes with a Chiral Multifunctional Organocatalyst

Hou, Wenduan; Zheng, Bo; Chen, Jun; Peng, Yungui, Organic Letters, 2012, 14(9), 2378-2381

Production Method 2

1315305-97-5

953805-46-4

Reaction Conditions

1.1 Reagents: 2-Methoxy-4-morpholinoaniline Solvents: Isopropanol ;  6 h, 120 °C
1.2 Solvents: Dichloromethane ;  overnight, rt

Reference

Methanesulfonamido-cyclohexylamine derivatives of 2,4-diaminopyrimidine as potent ALK inhibitors

Zificsak, Craig A.; Theroff, Jay P.; Aimone, Lisa D.; Angeles, Thelma S.; Albom, Mark S.; et al, Bioorganic & Medicinal Chemistry Letters, 2011, 21(13), 3877-3880

N-[(1S,2S)-2-氨基環(huán)己基]甲磺酸酰胺 Raw materials

• N-[(1S,2S)-2-[(2,5-Dichloro-4-pyrimidinyl)amino]cyclohexyl]methanesulfonamide
• (1S,2S)-cyclohexane-1,2-diamine

N-[(1S,2S)-2-氨基環(huán)己基]甲磺酸酰胺 Preparation Products

• N-[(1S,2S)-2-氨基環(huán)己基]甲磺酸酰胺 (953805-46-4)

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N-[(1S,2S)-2-Aminocyclohexyl]methanesulfonamide: A Comprehensive Overview

N-[(1S,2S)-2-Aminocyclohexyl]methanesulfonamide (CAS No. 953805-46-4) is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, also known as (1S,2S)-N-(2-Aminocyclohexyl)methanesulfonamide, is characterized by its unique structural features and potential biological activities. In this comprehensive overview, we will delve into the chemical properties, synthesis methods, biological activities, and recent research advancements associated with this compound.

The molecular structure of N-[(1S,2S)-2-Aminocyclohexyl]methanesulfonamide consists of a cyclohexane ring with an amino group and a methanesulfonamide moiety. The presence of these functional groups imparts specific chemical and biological properties to the molecule. The amino group can participate in hydrogen bonding and other interactions, making it a valuable component in drug design. The methanesulfonamide group, on the other hand, is known for its ability to modulate various biological processes.

In terms of chemical synthesis, N-[(1S,2S)-2-Aminocyclohexyl]methanesulfonamide can be prepared through several routes. One common method involves the reaction of (1S,2S)-2-aminocyclohexanol with methanesulfonyl chloride in the presence of a base such as triethylamine. This reaction yields the desired product with high purity and yield. Another approach involves the use of transition metal-catalyzed reactions to achieve stereoselective synthesis, which is crucial for obtaining the (1S,2S) configuration.

The biological activities of N-[(1S,2S)-2-Aminocyclohexyl]methanesulfonamide have been extensively studied in recent years. One of its notable applications is in the field of neuropharmacology, where it has shown potential as a modulator of ion channels and receptors. For instance, research has demonstrated that this compound can interact with N-methyl-D-aspartate (NMDA) receptors, which are involved in synaptic plasticity and learning processes. This interaction could have implications for the treatment of neurological disorders such as Alzheimer's disease and Parkinson's disease.

Additionally, N-[(1S,2S)-2-Aminocyclohexyl]methanesulfonamide has been investigated for its anti-inflammatory properties. Studies have shown that it can inhibit the production of pro-inflammatory cytokines such as interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-α). These findings suggest that the compound may have therapeutic potential in inflammatory conditions such as rheumatoid arthritis and inflammatory bowel disease.

In the context of cancer research, N-[(1S,2S)-2-Aminocyclohexyl]methanesulfonamide has been explored for its ability to induce apoptosis in cancer cells. Preclinical studies have demonstrated that it can selectively target cancer cells while sparing normal cells, making it a promising candidate for cancer therapy. The mechanism by which it exerts these effects is not yet fully understood but may involve modulation of signaling pathways such as p53 and Bcl-2.

Recent advancements in computational chemistry have also contributed to our understanding of N-[(1S,2S)-2-Aminocyclohexyl]methanesulfonamide. Molecular docking studies have provided insights into its binding interactions with various protein targets. These computational models can help guide the design of more potent and selective analogs for therapeutic applications.

Clinical trials involving N-[(1S,2S)-2-Aminocyclohexyl]methanesulfonamide are currently underway to evaluate its safety and efficacy in human subjects. Early results from phase I trials have shown promising outcomes with regard to tolerability and pharmacokinetic properties. However, further studies are needed to fully assess its therapeutic potential across different indications.

In conclusion, N-[(1S,2S)-2-Aminocyclohexyl]methanesulfonamide (CAS No. 953805-46-4) is a multifaceted compound with diverse biological activities and potential therapeutic applications. Its unique chemical structure and functional groups make it an attractive candidate for drug development in areas such as neuropharmacology, inflammation, and cancer therapy. Ongoing research continues to uncover new insights into its mechanisms of action and clinical utility.

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