Synthesis and Cytotoxicity of Dinaphtho[2, 1-b:1',2'-d]furan Derivatives

被引:1
|
作者
Song, Yongbin [1 ]
Li, Dan [2 ]
Yang, Yihui [2 ]
Ji, Hongrui [1 ]
Liu, Bo [1 ]
机构
[1] Harbin Univ Sci & Technol, Sch Chem & Environm Engn, Harbin 150040, Heilongjiang, Peoples R China
[2] Harbin Med Univ, Coll Pharm, Harbin 150081, Heilongjiang, Peoples R China
关键词
synthesis design; cytotoxicity; dinaphthofuran; NMR spectroscopy; BEARING; NAPHTHOFURAN;
D O I
10.6023/cjoc201712018
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In order to study the structure-activity relationships of dinaphthofuran derivatives, two series of dinaphtho[2,l-b:1', 2'-d]furan derivatives were synthesized. The structures of all compounds were identified by H-1 NMR, C-13 NMR, HRMS and IR spectra. The in vitro antitumor activity of the synthesized derivatives was tested by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. Most of them exhibited strong inhibitory activity on human hepatocellular carcinoma cell lines (HepG2 and SMMC-7721 cells), uterine cervix cancer Hela cells and acute promyelocytic leukemia NB4 cells. Compound 13k exhibited significant inhibitory activity against SMMC-7721 cells with IC50 vaue of 0.57 mu mol.L-1, much lower than 20.21 mu mol.L-1 of the positive control 5-Fu.
引用
收藏
页码:1516 / 1524
页数:9
相关论文
共 23 条
  • [1] Effects of reaction temperature and acyl group for lipase-catalyzed chiral binaphthol synthesis
    Aoyagi, Naoto
    Ogawa, Naomi
    Izumi, Taeko
    [J]. TETRAHEDRON LETTERS, 2006, 47 (28) : 4797 - 4801
  • [2] Binary heterocyclic systems containing the ethylideneamino linkage:: synthesis of some new heterocyclic compounds bearing the naphtho-[2,1-b]furan moiety
    Bedair, A. H.
    Abd El-Wahab, A. H. F.
    El-Agrody, A. M.
    Ali, F. M.
    Halawa, A. H.
    El-Sherbiny, G. M.
    [J]. JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2006, 71 (05) : 459 - 469
  • [3] New rigid angular dicarboxylic acid for the construction of nanoscopic supramolecules: From a molecular rectangle to a 1-D coordination polymer
    Cui, Y
    Ngo, HL
    Lin, WB
    [J]. INORGANIC CHEMISTRY, 2002, 41 (05) : 1033 - 1035
  • [4] Structures, biological activities, and total syntheses of 13-hydroxy- and 13-acetoxy-14-nordehydrocacalohastine, novel modified furanoeremophilane-type sesquiterpenes from Trichilia cuneata
    Doe, M
    Shibue, T
    Haraguchi, H
    Morimoto, Y
    [J]. ORGANIC LETTERS, 2005, 7 (09) : 1765 - 1768
  • [5] New pyranonaphthoquinone and pyranonaphthohydroquinone from the roots of Pentas longiflora
    El-Hady, S
    Bukuru, J
    Kesteleyn, B
    Van Puyvelde, L
    Van, TN
    De Kimpe, N
    [J]. JOURNAL OF NATURAL PRODUCTS, 2002, 65 (09): : 1377 - 1379
  • [6] Synthesis, Reactions and Biological Evaluation of Some New Naphtho[2,1-b]furan Derivatives Bearing a Pyrazole Nucleus
    El-Wahab, Ashraf H. F. Abd
    Al-Fifi, Zarrag Isa A.
    Bedair, Ahmed H.
    Ali, Fawzy M.
    Halawa, Ahmed H. A.
    El-Agrody, Ahemed M.
    [J]. MOLECULES, 2011, 16 (01) : 307 - 318
  • [7] Antipruritic dinaphthofuran-7,12-dione derivatives from the pericarp of Impatiens balsamina
    Ishiguro, K
    Ohira, Y
    Oku, H
    [J]. JOURNAL OF NATURAL PRODUCTS, 1998, 61 (09): : 1126 - 1129
  • [8] ITOKAWA H, 1993, CHEM PHARM BULL, V41, P1869, DOI 10.1248/cpb.41.1869
  • [9] Substrate-Mediated C-C and C-H Coupling after Dehalogenation
    Kong, Huihui
    Yang, Sha
    Gao, Hongying
    Timmer, Alexander
    Hill, Jonathan P.
    Arado, Oscar Diaz
    Moenig, Harry
    Huang, Xinyan
    Tang, Qin
    Ji, Qingmin
    Liu, Wei
    Fuchs, Harald
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (10) : 3669 - 3675
  • [10] Xylarianaphthol-1, a novel dinaphthofuran derivative, activates p21 promoter in a p53-independent manner
    Kotoku, Naoyuki
    Higashimoto, Kenichi
    Kurioka, Masatoshi
    Arai, Masayoshi
    Fukuda, Akinori
    Sumii, Yuji
    Sowa, Yoshihiro
    Sakai, Toshiyuki
    Kobayashi, Motomasa
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (15) : 3389 - 3391