Synthesis of Some 1-(Flavon-7-yl)-4,5-dihydro-1,2,4-triazin-6(1H)-ones and Related Congeners

被引:0
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作者
Abu-Aisheh, Marwa N. [2 ]
Mustafa, Mohammad S. [2 ]
Mubarak, Mohammad S. [2 ]
El-Abadelah, Mustafa M. [2 ]
Voelter, Wolfgang [1 ]
机构
[1] Univ Tubingen, Interfak Inst Biochem, D-72076 Tubingen, Germany
[2] Univ Jordan, Fac Sci, Dept Chem, Amman 11942, Jordan
关键词
7-Aminoflavone; 7-amino-2-methylchromen-4-one; 4-oxo-N-(chromen-7-yl) hydrazonoyl chlorides; antitumor activity L-alpha-amino esters; nitrileimine; substituted dihydro-1,2,4-triazin-6-ones; TRANSITION-METAL-COMPLEXES; NITROGEN SYSTEMS BEARING; DERIVATIZED CHIRAL DIHYDRO-1,2,4-TRIAZIN-6-ONES; ANTI-HIV; 1,2,4-TRIAZINE MOIETY; ANTICANCER DRUGS; STRUCTURAL-CHARACTERIZATION; FLAVONE DERIVATIVES; ANTIFUNGAL ACTIVITY; AGENTS;
D O I
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中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, a selected set of chiral N1-(4-oxochromen-7-yl)-4,5-dihydro-1,2,4-triazin-6(1H)-ones (7a-k / 8a-k) were prepared via direct interaction of L-alpha-amino esters with N1-(4-oxochromen-7-yl) nitrile imines (generated in situ from their hydrazonoyl chloride precursors 5a,b by the action of triethylamine). These novel dihydrotriazinone-flavone hybrid compounds (7), their 2- methylchromenone analogs (8) and the L-proline homologs (9,10) were characterized by microanalytical and spectral (HRMS and NMR) data. Compounds 7a and 7i displayed good activity against (MCF-7) breast cancer.
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页码:465 / 473
页数:9
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