One-Pot Synthesis of Novel Antiproliferative 9-Aminoacridines

被引:13
作者
Gellerman, Gary [1 ]
Waintraub, Sagiv [1 ,2 ]
Albeck, Amnon [2 ]
Gaisin, Vladimir [1 ]
机构
[1] Ariel Univ, Dept Biol Chem, Ctr Samaria, IL-40700 Ariel, Israel
[2] Bar Ilan Univ, Dept Chem, Julius Spokojny Bioorgan Chem Lab, IL-52900 Ramat Gan, Israel
关键词
9-Aminoacridine; addition-elimination; Nucleophilic substitution; one-pot synthesis; anticancer; Quinones; ACRIDINE-DERIVATIVES; ANTITUMOR-ACTIVITY; AGENTS; INHIBITORS; REDUCTASE;
D O I
10.1002/ejoc.201100133
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly efficient one-pot syntheses of antiproliferative 9-aminoacridine (9-AA) derivatives are described. Simple SNAr and addition/elimination reactions, using readily accessible starting materials, give a fast entry to novel 9-(pyridylamino)acridines, 9-(pyrimidinylamino)acridines and potential "dual-function" bioreductive 9-(acridinylamino)quinone intercalators. The synthetic routes reported in this work are general and readily applicable, significantly expanding the range and scope of potential 9-AA anticancer candidates.
引用
收藏
页码:4176 / 4182
页数:7
相关论文
共 41 条
  • [1] Allison J L, 1965, Antimicrob Agents Chemother (Bethesda), V5, P310
  • [2] New quinone-amino acid conjugates linked via a vinylic spacer
    Alnabari, M
    Bittner, S
    [J]. AMINO ACIDS, 2001, 20 (04) : 381 - 387
  • [3] NUCLEOPHILIC DISPLACEMENTS OF ACTIVATED FLUORINE IN AROMATIC COMPOUNDS
    BADER, H
    HANSEN, AR
    MCCARTY, FJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (07) : 2319 - &
  • [4] Inhibition of Trypanosoma cruzi trypanothione reductase by acridines:: Kinetic studies and structure-activity relationships
    Bonse, S
    Santelli-Rouvier, C
    Barbe, J
    Krauth-Siegel, RL
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (26) : 5448 - 5454
  • [5] Heat-induced formation of reactive oxygen species and 8-oxoguanine, a biomarker of damage to DNA
    Bruskov, VI
    Malakhova, LV
    Masalimov, ZK
    Chernikov, AV
    [J]. NUCLEIC ACIDS RESEARCH, 2002, 30 (06) : 1354 - 1363
  • [6] STRUCTURE-ACTIVITY-RELATIONSHIPS AND MODES OF ACTION OF 9-ANILINOACRIDINES AGAINST CHLOROQUINE-RESISTANT PLASMODIUM-FALCIPARUM INVITRO
    CHAVALITSHEWINKOON, P
    WILAIRAT, P
    GAMAGE, S
    DENNY, W
    FIGGITT, D
    RALPH, R
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1993, 37 (03) : 403 - 406
  • [7] DENNY W, 1992, ANTIMICROB AGENTS CH, V36, P1644
  • [8] Denny WA, 2002, CURR MED CHEM, V9, P1655
  • [9] Lysosomotropic agents and cysteine protease inhibitors inhibit scrapie-associated prion protein accumulation
    Doh-Ura, K
    Iwaki, T
    Caughey, B
    [J]. JOURNAL OF VIROLOGY, 2000, 74 (10) : 4894 - 4897
  • [10] Activity of pyronaridine and mepacrine against twelve strains of Plasmodium falciparum in vitro
    Elueze, EI
    Croft, SL
    Warhurst, DC
    [J]. JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 1996, 37 (03) : 511 - 518