Synthesis, characterization, and biological target prediction of novel 1,3-dithiolo[4,5-b]quinoxaline and thiazolo[4,5-b]quinoxaline derivatives

• Published in: Heterocyclic Communications Vol. 29; no. 1; pp. 10 - 39
• Main Authors: El-Gaby Mohamed S. A., Ammar Yousry A., Ismail Mostafa A., Ragab Ahmed, Abusaif Moustafa S.
• Format: Journal Article
• Language: English
• Published: Berlin Walter de Gruyter GmbH 25.12.2023; De Gruyter
• Subjects: 1,3-binucleophile; 1,3-dithiolo[4,5-b]quinoxaline; 2,3-dichloroquinoxaline; Artificial intelligence; biological target prediction; Chemical synthesis; Heterocyclic compounds; Imines; Infrared analysis; Infrared spectroscopy; Materials science; NMR; Nuclear magnetic resonance; Organic chemistry; Potassium salts; Quinoxalines; Room temperature; Spectrum analysis; thiazolo[4,5-b]quinoxaline
• ISSN: 0793-0283; 2191-0197
• DOI: 10.1515/hc-2022-0170

Quinoxalines are a family of nitrogen-based heterocyclic compounds that have garnered much interest because of their wide range of applications. 2,3-Dichloroquinoxaline is an aromatic molecule that frequently serves as a synthetic intermediate in materials science, pharmaceuticals, and organic chemistry. 1,3-Dithiolo[4,5-b]quinoxaline derivatives 8a–c and thiazolo[4,5-b]quinoxaline derivatives 11a,b were synthesized by the reaction of 2,3-dichloro-6-sulfonyl quinoxaline derivative 5 with 1,3-binucleophiles. Moreover, 1,3-dithiolo[4,5-b]quinoxalin2-ylidene derivatives 8a–c were obtained by treating 2,3-dichloro-6-sulfonyl quinoxaline derivative 5 with potassium salts of hydrazonodithioates 7a–c at room temperature. Additionally, 2,3-dichloroquinoxaline derivative 5 was reacted with thioureas 9a,b in 1,4-dioxane to yield 6-(pyrrolidin-1-yl sulfonyl)thiazolo[4,5-b]quinoxalin-2(3H)-imines 11a,b rather than thiazolo[5,4-b]quinoxaline 10. Elemental analysis, infrared spectroscopy, 1H NMR, 13C NMR, and mass spectroscopy were used to confirm the structures of the newly synthesized compounds. Finally, we used artificial intelligence to perform biological evaluation via predicting the possible molecular targets and antimicrobial activity of the designed derivative. The results showed good bacterial activity, weak fungal potency, and potential biological targets.