Synthesis and in Vitro Anti-Tumor Activity of A New Class of Acyclic Thioglycosides

被引:5
|
作者
Elgemeie, G. H. [1 ]
Saber, N. M. [2 ]
机构
[1] Helwan Univ, Fac Sci, Dept Chem, Cairo, Egypt
[2] Suez Canal Univ, Fac Sci, Dept Chem, Suez, Egypt
来源
关键词
antitumor activity; HEPG2; Acyclic thioglycosides; sodium; 2-cyano-ethylene-1-thiolates; ANTIMETABOLITES; AGENTS;
D O I
10.1080/15257770.2015.1016168
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The reaction of sodium 2-cyano-ethylene-1-thiolate salts with 2,3,4,6-tetra-O-acetyl-D-gluco- and D-galactopyranosyl bromides and with 2,3,4-tri-O-acetyl-D-xylo-. and L-arabinopyranosyl bromides, respectively, afforded new thioglycosides. Heating of the resultout glycosides with hydrazine produced pyrazole derivatives. The cytotoxicities toward the hepatoma cell line (HEPG2) of some synthesized compounds were tested. Some compounds showed high cytotoxic activity against (HEPG2) cell line. The OH moieties in the free glycosides were vital for potency. The synthesis procedures, spectroscopic data and antitumor activities for the prepared compounds are reported herein.
引用
收藏
页码:463 / 474
页数:12
相关论文
共 50 条
  • [31] SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF NEW NORBORNYL SYSTEM BASED OXADIAZOLE THIOGLYCOSIDES AND ACYCLIC NUCLEOSIDE ANALOGS
    Mohamed, Ashraf M.
    El-Sayed, Wael A.
    Al-Qalawi, Husam R. M.
    Germoush, Mousa O.
    ACTA POLONIAE PHARMACEUTICA, 2014, 71 (05): : 771 - 780
  • [32] DIALKYLTIN DIHALIDE COMPLEXES - NEW CLASS OF METALLIC DERIVATIVES EXHIBITING ANTI-TUMOR ACTIVITY
    CROWE, AJ
    SMITH, PJ
    CHEMISTRY & INDUSTRY, 1980, (05) : 200 - 201
  • [33] Anti-tumor activity of the heterocyclic hydrazones (HCHs), A new class of experimental antitumor agent
    Chu, Lily
    Liu, Lanzhen
    Song, Bai L.
    Wang, Qin
    Du, Yuefen
    Lin, Xu K.
    Belcourt, Michael F.
    King, Ivan Ch-L.
    Zheng, Li-Mou
    CANCER RESEARCH, 2006, 66 (08)
  • [34] TETROCARCINS, NEW ANTI-TUMOR ANTIBIOTICS .3. ANTI-TUMOR ACTIVITY OF TETROCARCIN-A
    MORIMOTO, M
    FUKUI, M
    OHKUBO, S
    TAMAOKI, T
    TOMITA, F
    JOURNAL OF ANTIBIOTICS, 1982, 35 (08): : 1033 - 1037
  • [35] SYNTHESIS, ANTI-TUMOR ACTIVITY, AND CARDIAC TOXICITY OF NEW 4-DEMETHOXYANTHRACYCLINES
    PENCO, S
    CASAZZA, AM
    FRANCHI, G
    BARBIERI, B
    BELLINI, O
    PODESTA, A
    SAVI, G
    PRATESI, G
    GERONI, C
    DIMARCO, A
    ARCAMONE, F
    CANCER TREATMENT REPORTS, 1983, 67 (7-8): : 665 - 673
  • [36] Synthesis of the new pseudo-symmetrical tamoxifen derivatives and their anti-tumor activity
    Shiina, Isamu
    Sano, Yoshiyuki
    Nakata, Kenya
    Kikuchi, Takaaki
    Sasaki, Akane
    Ikekita, Masahiko
    Hasome, Yoshimune
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (09) : 2421 - 2424
  • [37] NEW DIMERIC ANALOGS OF ETHIDIUM - SYNTHESIS, INTERACTION WITH DNA, AND ANTI-TUMOR ACTIVITY
    KUHLMANN, KF
    MOSHER, CW
    JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (11) : 1333 - 1337
  • [38] A total synthesis of a new class of biazine thioglycosides
    Elgemeie, GH
    Hussein, MM
    Al-Khursani, SA
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 2004, 23 (8-9) : 465 - 481
  • [39] ANTI-TUMOR AGENTS .32. SYNTHESIS AND ANTI-TUMOR ACTIVITY OF CYCLOPENTENONE DERIVATIVES RELATED TO HELENALIN
    LEE, KH
    MAR, EC
    OKAMOTO, M
    HALL, IH
    JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (08) : 819 - 822
  • [40] POTENTIAL ANTI-TUMOR AGENTS .9. SYNTHESIS AND ANTI-TUMOR ACTIVITY OF 2 ANALOGS OF KETOCAINE
    ANDREANI, A
    SCAPINI, G
    GALATULAS, I
    BOSSA, R
    JOURNAL OF PHARMACEUTICAL SCIENCES, 1983, 72 (07) : 814 - 815