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

被引：5

作者：

Sheikhi-Mohammareh, Seddigheh ^{[1
]}

Oroojalian, Fatemeh ^{[2
,3
]}

Beyzaei, Hamid ^{[4
]}

Moghaddam-Manesh, Mohammadreza ^{[5
]}

Salimi, Alireza ^{[1
]}

Azizollahi, Fatemeh ^{[2
]}

Shiri, Ali ^{[1
]}

机构：

[1] Ferdowsi Univ Mashhad, Fac Sci, Dept Chem, Mashhad, Iran

[2] North Khorasan Univ Med Sci, Sch Med, Dept Adv Sci & Technol, Bojnurd, Iran

[3] North Khorasan Univ Med Sci, Nat Prod & Med Plants Res Ctr, Bojnurd, Iran

[4] Univ Zabol, Fac Sci, Dept Chem, Zabol, Iran

[5] Iranian Natl Stand Org, Gen Bur Stand Sistan & Baluchestan Prov, Zahedan, Iran

来源：

TALANTA | 2023年 / 262卷

关键词：

One-pot; Quinoxaline; Fluorescent; Antioxidant; Anticancer; Pyrazolo[1; 5-a]pyrimidine; thiazino[2; 3-b]quinoxaline; QUINOXALINE DERIVATIVES; REGIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATION; EFFICIENT PROTOCOL; ONE-POT; ANTIBACTERIAL; ANTIFUNGAL; CATALYST; CELLS; DOXORUBICIN;

D O I：

10.1016/j.talanta.2023.124723

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

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.

引用

页数：11

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