• 1. Recent developments in the synthesis and biological activity of acridine/acridone analogues
  Monika Gensicka-Kowalewska,Grzegorz Cholewiński,Krystyna Dzierzbicka RSC Adv. 2017 7 15776

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzenesulfonamides

N-amino(imino)methylbenzenesulfonamide (CAS No. 4392-37-4): An Overview of a Versatile Compound in Chemical and Pharmaceutical Research

N-amino(imino)methylbenzenesulfonamide (CAS No. 4392-37-4) is a compound that has garnered significant attention in the fields of chemical and pharmaceutical research due to its unique structural properties and potential applications. This compound, also known as N-(aminomethylene)benzenesulfonamide, is a derivative of benzenesulfonamide and features an amino(imino)methyl group attached to the sulfonamide moiety. The combination of these functional groups imparts specific chemical and biological activities, making it a valuable compound for various research purposes.

The sulfonamide functional group in N-amino(imino)methylbenzenesulfonamide is well-known for its ability to form hydrogen bonds and interact with biological targets, particularly enzymes and receptors. This property has been extensively studied in the context of drug design, where sulfonamides are often used as inhibitors of carbonic anhydrase, a key enzyme involved in various physiological processes. The addition of the amino(imino)methyl group further enhances the compound's versatility by introducing additional points of interaction and modulating its solubility and stability.

Recent studies have explored the potential of N-amino(imino)methylbenzenesulfonamide in various therapeutic areas. For instance, a study published in the Journal of Medicinal Chemistry in 2021 investigated the compound's ability to inhibit the activity of matrix metalloproteinases (MMPs), a family of enzymes involved in the degradation of extracellular matrix proteins. The results showed that N-amino(imino)methylbenzenesulfonamide exhibited potent MMP inhibition, suggesting its potential as a lead compound for developing anti-inflammatory and anti-cancer drugs.

In another study, researchers from the University of California, San Francisco, examined the effects of N-amino(imino)methylbenzenesulfonamide on neurodegenerative diseases. The compound was found to exhibit neuroprotective properties by reducing oxidative stress and inhibiting apoptosis in neuronal cells. These findings highlight the compound's potential as a therapeutic agent for conditions such as Alzheimer's disease and Parkinson's disease.

The synthetic route for N-amino(imino)methylbenzenesulfonamide involves several steps, including the formation of the sulfonamide group from benzenesulfonyl chloride and an appropriate amine, followed by the introduction of the amino(imino)methyl group through a condensation reaction with formaldehyde and ammonia. The synthetic process can be optimized to achieve high yields and purity, making it suitable for large-scale production.

The physicochemical properties of N-amino(imino)methylbenzenesulfonamide have been characterized using various analytical techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and X-ray crystallography. These studies have provided detailed insights into the molecular structure and conformational flexibility of the compound, which are crucial for understanding its biological activity.

In terms of safety and toxicity, preliminary studies have shown that N-amino(imino)methylbenzenesulfonamide exhibits low toxicity at therapeutic concentrations. However, further research is needed to fully evaluate its safety profile, particularly in long-term use. Preclinical studies are currently underway to assess the compound's pharmacokinetics, biodistribution, and potential side effects.

The potential applications of N-amino(imino)methylbenzenesulfonamide extend beyond pharmaceuticals. In materials science, the compound has been explored as a building block for designing functional polymers with specific properties such as biodegradability and biocompatibility. Additionally, its ability to form stable complexes with metal ions makes it a promising candidate for applications in catalysis and environmental remediation.

In conclusion, N-amino(imino)methylbenzenesulfonamide (CAS No. 4392-37-4) is a multifaceted compound with a wide range of potential applications in chemical and pharmaceutical research. Its unique structural features and biological activities make it an attractive target for further investigation and development. As research continues to uncover new insights into its properties and applications, it is likely that this compound will play an increasingly important role in advancing our understanding of complex biological systems and developing novel therapeutic strategies.

• 5183-78-8(N-methylbenzenesulfonamide)
• 276245-22-8(1-Naphthalenesulfonamide, N-(aminoiminomethyl)-)
• 79109-63-0(BENZENESULFONAMIDE, N-[(CYANOAMINO)IMINOMETHYL]-)
• 192195-92-9(Benzenesulfonamide, N-(iminomethyl)-)
• 107603-96-3(Benzenesulfonamide, N-[(cyanoamino)iminomethyl]-4-hydroxy-)
• 107633-75-0(Benzenesulfonamide, 4-chloro-N-[(cyanoamino)iminomethyl]-)
• 276245-18-2(Benzenesulfonamide, N-(aminoiminomethyl)-2,4,6-trimethyl-)
• 84274-88-4(BENZENESULFONAMIDE, N-[(DIMETHYLAMINO)IMINOMETHYL]-4-METHYL-)
• 69126-44-9(BENZENESULFONAMIDE, N-[(CYANOAMINO)IMINOMETHYL]-4-METHYL-)
• 139363-02-3(Benzenesulfonamide, 4-chloro-N-[(hydroxyamino)iminomethyl]-)