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

被引：0
|
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
来源：
LETTERS IN ORGANIC CHEMISTRY | 2012年 / 9卷 / 07期
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：
暂无
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.
引用
收藏
页码：465 / 473
页数：9
相关论文
共 50 条
  • [31] Synthesis, biological evaluation and molecular docking studies of novel 1-(4,5-dihydro-1H-pyrazol-1-yl)ethanone-containing 1-methylindol derivatives as potential tubulin assembling inhibitors
    Yang, Meng-Ru
    Qin, Ya-Juan
    Chen, Chen
    Zhang, Ya-Liang
    Li, Bo-Yan
    Liu, Tian-Bao
    Gong, Hai-Bin
    Wang, Bao-Zhong
    Zhu, Hai-Liang
    RSC ADVANCES, 2016, 6 (36): : 30412 - 30424
  • [32] Synthesis, structure and antibacterial activity of new 2-(1-(2-(substituted-phenyl)5-methyloxazol-4-yl)-3-(2-substitued-phenyl)-4,5-dihydro-1H-pyrazol-5-yl)-7-substitued-1,2,3,4-tetrahydroisoquinoline derivatives
    Liu, Xin-Hua
    Zhu, Jing
    Zhou, An-na
    Song, Bao-An
    Zhu, Hai-Liang
    bai, Lin-Shan
    Bhadury, Pinaki S.
    Pan, Chun-Xiu
    BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (03) : 1207 - 1213
  • [33] Design, synthesis and antifungal evaluation of 1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,4-triazol-5(4H)-one
    Jiang, Yongwei
    Cao, Yongbin
    Zhang, Jun
    Zou, Yan
    Chai, Xiaoyun
    Hu, Honggang
    Zhao, Qingjie
    Wu, Qiuye
    Zhang, Dazhi
    Jiang, Yuanying
    Sun, Qingyan
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (07) : 3135 - 3141
  • [34] Synthesis and Cytotoxicity Evaluation of Some Novel Thiazoles, Thiadiazoles, and Pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones Incorporating Triazole Moiety
    Gomha, Sobhi M.
    Ahmed, Sayed A.
    Abdelhamid, Abdou O.
    MOLECULES, 2015, 20 (01): : 1357 - 1376
  • [35] SYNTHESIS CHARACTERIZATION AND BIOLOGICAL EVALUATION OF NOVEL OF (1E)-1-((9-((4,5-DIHYDRO-5-THIOXO-1,3,4-OXADIAZOL-2-YL)METHYL)-9H-CARBAZOL-6-YL)METHYLENE)THIOSEMICARBAZIDE BEARING PHENYL THIAZOLE
    Krishna, S. Murali
    Raveendra, M.
    HETEROCYCLIC LETTERS, 2019, 9 (04): : 481 - 486
  • [36] NOVEL ONE-POT MULTICOMPONENT SYNTHESIS OF SUBSTITUTED 2,3-DIHYDRO-2-(6-(4-HYDROXY-6-METHYL-2-OXO-2H-PYRAN-3-YL)-7H-[1,2,4] TRIAZOLO[3,4-b][1,3,4] THIADIAZIN-3-YL) PHTHALAZINE-1,4-DIONES AND SUBSTITUTED 3-[3-(N'-BENZYLIDENE-HYDRAZINO)-7H-[1,2,4] TRIAZOLO[3,4-b][1,3,4] THIADIAZIN-6-YL]-4-HYDROXY-6-METHYL-PYRAN-2-ONES
    Thirupaiah, Bade
    Vedula, Rajeswar Rao
    SYNTHETIC COMMUNICATIONS, 2014, 44 (04) : 513 - 519
  • [37] A facile one-pot synthesis of 6,7,8,9-tetrahydrobenzo[4,5] thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-5-ones
    Gomha, Sobhi M.
    MONATSHEFTE FUR CHEMIE, 2009, 140 (02): : 213 - 220
  • [38] SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF 2-PHENYL-3-{1-CYCLOPROPYL-6-FLUORO-7-[4-METHYLPIPERAZIN-1-YL]-4-QUINOLONE}CARBOXAMIDO-3-THIAZOLIDIN-4-ONES
    Patel, N. B.
    Patel, S. D.
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2009, 43 (06) : 305 - 310
  • [39] Synthesis and Biological Activity of Some 3,4-Dihydro-4-(4-substituted aryl)-6-(naptho [2,1-b]furan-2-yl pyrimidine-2(1H)-one Derivatives
    Gaikwad, Sanjeevan S.
    Suryawanshi, Venkat S.
    Lohar, Kishan S.
    Jadhav, Dhanaji V.
    Shinde, Narayan D.
    E-JOURNAL OF CHEMISTRY, 2012, 9 (01) : 175 - 180
  • [40] Synthesis and Antifungal Activity of Some Novel (E)-2, 3-Dihydro-3-[(phenylamino) methylene]-4H-1-benzothiopyran-4-ones
    Liu Xiao-Ming
    Yang Geng-Liang
    Song Ya-Li
    Liu Jie-Jie
    Wang Yang
    Zhang Dong-Nuan
    LETTERS IN ORGANIC CHEMISTRY, 2013, 10 (03) : 228 - 234
12345