4.7 Article

Domino protocol for the synthesis of diversely functionalized derivatives of a novel fused pentacyclic antioxidant/anticancer fluorescent scaffold: Pyrazolo[5,1:2',3']pyrimido[4',5':5,6][1,4]thiazino[2,3-b]quinoxaline

Journal

TALANTA
Volume 262, Issue -, Pages -

Publisher

ELSEVIER
DOI: 10.1016/j.talanta.2023.124723

Keywords

One-pot; Quinoxaline; Fluorescent; Antioxidant; Anticancer; Pyrazolo[1; 5-a]pyrimidine; thiazino[2; 3-b]quinoxaline

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An efficient one-pot two-step procedure was established for the synthesis of novel pyrazolo[5,1:2,3']pyrimido[4,5':5,6][1,4]thiazino[2,3-b]quinoxalines from easily accessible starting materials. The synthesized compounds showed significant antioxidant activity and can be used as fluorescent markers and probes in biochemistry and pharmacology studies.
Rising to the challenge of formidable multi-step reaction needed for the synthesis of polycyclic compounds, an efficient one-pot two-step procedure for the synthesis of densely functionalized novel pyrazolo[5 & DPRIME;,1:2 & PRIME;,3'] pyrimido[4 & PRIME;,5':5,6] [1,4]thiazino[2,3-b]quinoxalines from synthetically accessible starting materials 6-bromo-7chloro-3-cyano-2-(ethylthio)-5-methylpyrazolo[1,5-a]pyrimidine, 3-aminoquinoxaline-2-thiol and some readily accessible alkyl halides was established. The domino reaction pathway involves cyclocondensation/N-alkylation sequence in K2CO3/N,N-dimethyl formamide under heating condition. DPPH free radical scavenging activity of all synthesized pyrazolo[5 & DPRIME;,1:2 & PRIME;,3']pyrimido[4 & PRIME;,5':5,6][1,4]thiazino[2,3-b]quinoxalines was evaluated to determine their antioxidant potentials. IC50 values were recorded in the range of 29-71 & mu;M. N-benzyl substituted derivative represented the most effective antioxidant activity as well as antiproliferative activity against MCF-7 cells. Moreover, fluorescence in solution for these compounds exhibited strong red emission in the visible region (& lambda;flu. = 536-558 nm) with good to excellent quantum yields (61-95%). Due to their interesting fluorescence properties, these novel pentacyclic fluorophores can be used as fluorescent markers and probes for studies in biochemistry and pharmacology.

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