• 1. An unexpected reversal in the pharmacological stereoselectivity of benzothiadiazine AMPA positive allosteric modulators
  Umberto M. Battisti,Cinzia Citti,Giulio Rastelli,Luca Pinzi,Giulia Puja,Federica Ravazzini,Giuseppe Ciccarella,Daniela Braghiroli,Giuseppe Cannazza Med. Chem. Commun. 2016 7 2410

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Aminobenzenesulfonamides
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzenesulfonamides Aminobenzenesulfonamides
• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

Introduction to 2-Amino-5-chlorobenzenesulfonamide (CAS No. 5790-69-2) and Its Recent Applications in Chemical Biology

2-Amino-5-chlorobenzenesulfonamide, identified by the Chemical Abstracts Service Number (CAS No.) 5790-69-2, is a heterocyclic organic compound that has garnered significant attention in the field of chemical biology due to its versatile structural properties and potential applications in drug discovery and medicinal chemistry. This compound belongs to the class of sulfonamides, which are well-documented for their broad spectrum of biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. The presence of both amino and chloro substituents in its molecular framework enhances its reactivity and makes it a valuable scaffold for further chemical modifications.

The sulfonamide functional group, characterized by the -SO?NH? moiety, is renowned for its ability to form hydrogen bonds and interact with biological targets such as enzymes and receptors. This property has been leveraged in the design of numerous therapeutic agents. Specifically, 2-Amino-5-chlorobenzenesulfonamide has been explored in the development of small-molecule inhibitors targeting various disease pathways. Its chloro substituent at the 5-position introduces electrophilic centers that can participate in nucleophilic substitution reactions, enabling the synthesis of derivatives with tailored biological activities.

In recent years, there has been a surge in research focused on exploiting sulfonamide derivatives for therapeutic purposes. Notably, studies have highlighted the potential of 2-Amino-5-chlorobenzenesulfonamide as a precursor in the synthesis of compounds that exhibit inhibitory effects on key enzymes involved in cancer progression. For instance, research published in leading journals such as *Journal of Medicinal Chemistry* and *Bioorganic & Medicinal Chemistry* has demonstrated its utility in generating inhibitors of kinases and other enzymes overexpressed in tumor cells. These findings underscore the compound's significance as a building block in oncology drug development.

Moreover, the structural features of 2-Amino-5-chlorobenzenesulfonamide make it an attractive candidate for further derivatization to enhance pharmacokinetic properties such as solubility, bioavailability, and metabolic stability. Researchers have employed various synthetic strategies, including nucleophilic aromatic substitution and condensation reactions, to modify its core structure. Such modifications have led to the identification of novel analogs with improved binding affinities and selectivity towards biological targets. This underscores the compound's versatility and its potential as a lead compound in medicinal chemistry campaigns.

Recent advancements in computational chemistry have further accelerated the exploration of 2-Amino-5-chlorobenzenesulfonamide derivatives. Molecular docking studies have been instrumental in predicting binding modes and interactions between sulfonamide-based compounds and their target proteins. These computational approaches have complemented experimental efforts by providing insights into structure-activity relationships (SARs) and guiding the design of next-generation inhibitors. The integration of machine learning algorithms has further refined these predictions, enabling more accurate modeling of drug-target interactions.

The antimicrobial properties of sulfonamides have also been revisited in light of emerging resistant strains of bacteria. 2-Amino-5-chlorobenzenesulfonamide has been investigated as a component in combination therapies aimed at overcoming resistance mechanisms. By acting on bacterial enzymes such as dihydropteroate synthase (DHPS), sulfonamides can disrupt folic acid biosynthesis, a critical pathway for bacterial growth. The chloro substituent enhances this effect by increasing electrophilicity, making it more susceptible to nucleophilic attack by bacterial enzymes. Such studies highlight the enduring relevance of sulfonamides in antimicrobial research.

In conclusion, 2-Amino-5-chlorobenzenesulfonamide (CAS No. 5790-69-2) represents a promising compound with diverse applications in chemical biology and drug discovery. Its unique structural features facilitate modifications that yield derivatives with enhanced biological activities. Ongoing research continues to uncover new therapeutic potentials for this compound, particularly in oncology and antimicrobial treatments. As computational methods advance, so too does our ability to harness its synthetic versatility for developing innovative therapeutic agents.

• 3306-62-5(2-Aminobenzenesulfonamide)
• 4140-83-4(2-amino-4-chlorobenzene-1-sulfonamide)
• 88345-43-1(1,4-Benzenedisulfonamide, 2-amino-3-chloro-)
• 22134-75-4(4-amino-3,5-dichlorobenzene-1-sulfonamide)
• 29092-34-0(3-Amino-4-chlorobenzenesulfonamide)
• 16948-63-3(Benzenesulfonamide,2-amino-4,5-dichloro-)
• 1083-36-9(4-Amino-5-chloro-1,3-benzenedisulfonamide)
• 121-30-2(4-Amino-6-chloro-1,3-benzenedisulfonamide)
• 20896-44-0(2,5-Diaminobenzenesulfonamide)
• 53297-68-0(4-amino-3-chloro-benzenesulfonamide)