Production Method 1

844646-86-2

844646-88-4

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Methanol ;  16 h, reflux; reflux → 23 °C
1.2 Reagents: Formic acid Solvents: Dimethylformamide ,  Water ;  23 °C → 0 °C
1.3 Reagents: Chlorine ;  5 min, 0 °C

Reference

Identification and Optimization of Anthranilic Sulfonamides as Novel, Selective Cholecystokinin-2 Receptor Antagonists

Allison, Brett D.; et al, Journal of Medicinal Chemistry, 2006, 49(21), 6371-6390

Production Method 2

844646-84-0

844646-88-4

Reaction Conditions

1.1 rt → 240 °C; 1 h, 240 °C
2.1 Reagents: Potassium hydroxide Solvents: Methanol ;  16 h, reflux; reflux → 23 °C
2.2 Reagents: Formic acid Solvents: Dimethylformamide ,  Water ;  23 °C → 0 °C
2.3 Reagents: Chlorine ;  5 min, 0 °C

Reference

Identification and Optimization of Anthranilic Sulfonamides as Novel, Selective Cholecystokinin-2 Receptor Antagonists

Allison, Brett D.; et al, Journal of Medicinal Chemistry, 2006, 49(21), 6371-6390

Production Method 3

17056-99-4

88-11-9

844646-88-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  1 h, 23 °C
1.2 2 h, 23 °C
1.3 Solvents: Water ;  23 °C
2.1 rt → 240 °C; 1 h, 240 °C
3.1 Reagents: Potassium hydroxide Solvents: Methanol ;  16 h, reflux; reflux → 23 °C
3.2 Reagents: Formic acid Solvents: Dimethylformamide ,  Water ;  23 °C → 0 °C
3.3 Reagents: Chlorine ;  5 min, 0 °C

Reference

Identification and Optimization of Anthranilic Sulfonamides as Novel, Selective Cholecystokinin-2 Receptor Antagonists

Allison, Brett D.; et al, Journal of Medicinal Chemistry, 2006, 49(21), 6371-6390

Quinoxaline-5-sulfonyl chloride Raw materials

• Quinoxalin-5-ol
• Carbamothioic acid, N,N-diethyl-, S-5-quinoxalinyl ester
• Carbamothioic acid, N,N-diethyl-, O-5-quinoxalinyl ester
• diethylthiocarbamoyl chloride

Quinoxaline-5-sulfonyl chloride Preparation Products

• Quinoxaline-5-sulfonyl chloride (844646-88-4)

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Introduction to Quinoxaline-5-sulfonyl chloride (CAS No. 844646-88-4)

Quinoxaline-5-sulfonyl chloride, identified by the chemical compound code CAS No. 844646-88-4, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical and medicinal chemistry. This compound belongs to the quinoxaline class of heterocyclic aromatic compounds, which are widely recognized for their diverse biological activities and potential applications in drug development. The introduction of the sulfonyl chloride functional group into the quinoxaline core enhances its reactivity, making it a valuable intermediate in synthetic chemistry and a promising candidate for further exploration in medicinal applications.

The structure of Quinoxaline-5-sulfonyl chloride consists of a fused ring system comprising a benzene ring and a pyrazine-like moiety, with a sulfonyl chloride substituent attached to the fifth position of the quinoxaline ring. This structural arrangement imparts unique chemical properties that make it particularly useful in organic synthesis. The sulfonyl chloride group is highly electrophilic, facilitating nucleophilic substitution reactions that are pivotal in constructing more complex molecular architectures. Such reactivity is leveraged in the synthesis of various pharmacophores, including those targeted in oncology, anti-inflammatory, and antimicrobial therapies.

In recent years, there has been growing interest in exploring the pharmacological potential of quinoxaline derivatives. The Quinoxaline-5-sulfonyl chloride compound has been studied for its ability to modulate enzyme activity and interact with biological targets. For instance, research has indicated that derivatives of this compound may exhibit inhibitory effects on certain kinases and other enzymes involved in cellular signaling pathways. These pathways are often dysregulated in diseases such as cancer, making quinoxaline-based compounds attractive candidates for therapeutic intervention.

One of the most compelling aspects of Quinoxaline-5-sulfonyl chloride is its versatility as a synthetic building block. The presence of the sulfonyl chloride group allows for facile introduction of various functional groups through nucleophilic aromatic substitution or addition reactions, enabling chemists to tailor the molecular structure for specific biological activities. This flexibility has been exploited in several studies aimed at developing novel drug candidates. For example, researchers have utilized this compound to synthesize analogs that target bacterial enzymes responsible for antibiotic resistance, highlighting its utility in combating emerging infectious diseases.

The synthesis of Quinoxaline-5-sulfonyl chloride typically involves multi-step organic transformations starting from readily available precursors. The process often begins with the formation of the quinoxaline core through condensation reactions between appropriate aldehydes and hydrazines. Subsequent functionalization at the fifth position with a sulfonyl chloride group is achieved through chlorosulfonation followed by reaction with thionyl chloride or phosphorus pentachloride. These synthetic routes have been optimized to ensure high yields and purity, making Quinoxaline-5-sulfonyl chloride accessible for further research and development.

Recent advancements in computational chemistry have also contributed to the study of Quinoxaline-5-sulfonyl chloride and its derivatives. Molecular modeling techniques allow researchers to predict the binding affinity and interactions of these compounds with biological targets, accelerating the drug discovery process. Such computational studies have identified promising lead structures that warrant further experimental validation. The integration of experimental data with computational insights provides a robust framework for understanding the mechanism of action and optimizing the pharmacological properties of quinoxaline-based compounds.

The pharmaceutical industry has taken note of the potential applications of Quinoxaline-5-sulfonyl chloride and related derivatives. Several academic and industrial research groups are actively investigating its use in developing new therapeutics. For example, preclinical studies have demonstrated that certain quinoxaline sulfonamides exhibit anti-proliferative effects on cancer cell lines by inhibiting key signaling pathways involved in tumor growth and survival. These findings underscore the importance of continued research into this class of compounds.

In addition to its pharmaceutical applications, Quinoxaline-5-sulfonyl chloride has shown promise in other areas, such as materials science and agrochemicals. Its unique structural features make it a suitable candidate for designing advanced materials with tailored properties. Furthermore, derivatives of this compound have been explored as intermediates in synthesizing novel agrochemicals that offer improved efficacy against pests while minimizing environmental impact.

The future prospects for Quinoxaline-5-sulfonyl chloride are bright, driven by ongoing research efforts aimed at expanding its applications and understanding its mechanisms of action. As our knowledge base grows, it is likely that new therapeutic uses will be uncovered, further solidifying its role as a cornerstone compound in medicinal chemistry. Collaborative efforts between academia and industry will be essential in translating these findings into tangible benefits for patients worldwide.

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