Synthesis and antitumor activity of substituted triazolo[4,3-a]pyrimidin-6-sulfonamide with an incorporated thiazolidinone moiety

被引：65
作者：
Hafez, Hend N. [1 ]
El-Gazzar, Abdel-Rahman B. A. [1 ]
机构：
[1] Natl Res Ctr, Photochem Dept, Heterocycl & Nucleoside Unit, Cairo 12622, Egypt
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 15期
关键词：
Triazolo[4,3-a]pyrimidine; Thioglycolic acid; Thiazolidinone; Anti-tumor; NATIONAL-CANCER-INSTITUTE; DRUG DISCOVERY; DERIVATIVES; ANTIOXIDANT; ANALOGS; DESIGN;
D O I：
10.1016/j.bmcl.2009.05.126
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Chlorosulfonation of 3-methyl[1,2,4]triazolo[4,3-a]pyrimidine with chlorosulfonic acid in the presence of thionyl chloride was studied. When triazolo[4,3-a]pyrimidines are used as substrates, the substitution occurs at C-6. Also the reactivity of the hydrazides (7) towards aldehydes, thioglycolic acid and amines were studies. The newly prepared compounds 10a,d and 11a,d demonstrated inhibitory effects on the growth of a wide range of cancer cell lines generally at 10 (5) M level and in some cases at 10 (7) M concentrations. (C) 2009 Elsevier Ltd. All rights reserved.
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页码：4143 / 4147
页数：5
相关论文
共 35 条
  • [1] [Anonymous], 1988, Pharmaceutical Chemistry Journal, DOI DOI 10.1007/BF00763528
  • [2] BERNIER JL, 1980, J PHARM SCI-US, V69, P1343, DOI 10.1002/jps.2600691128
  • [3] Boyd M.R., 1989, PRINCIPLES PRACTICES, V3, P1
  • [4] SOME PRACTICAL CONSIDERATIONS AND APPLICATIONS OF THE NATIONAL-CANCER-INSTITUTE IN-VITRO ANTICANCER DRUG DISCOVERY SCREEN
    BOYD, MR
    PAULI, KD
    [J]. DRUG DEVELOPMENT RESEARCH, 1995, 34 (02) : 91 - 109
  • [5] Biological profile of new apoptotic agents based on 2,4-pyrido[2,3-d]pyrimidine derivatives
    Cordeu, Lucia
    Cubedo, Elena
    Bandres, Eva
    Rebollo, Amaia
    Saenz, Xabi
    Chozas, Hector
    Dominguez, Ma Victoria
    Echeverria, Mikel
    Mendivil, Beatriz
    Sanmartin, Carmen
    Palop, Juan Antonio
    Font, Maria
    Garcia-Foncillas, Jestis
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (04) : 1659 - 1669
  • [6] NSAI ACTIVITY STUDY OF 4-PHENYL-2-THIOXO-BENZO[4,5]THIENO [2,3-D]PYRIMIDINE DERIVATIVES
    DARIAS, V
    ABDALLAH, SS
    TELLO, ML
    DELGADO, LD
    VEGA, S
    [J]. ARCHIV DER PHARMAZIE, 1994, 327 (12) : 779 - 783
  • [7] SYNTHESIS OF SOME NEW S-ALKYLATED DERIVATIVES OF 5-MERCAPTO-2'-DEOXYURIDINE AS POTENTIAL ANTI-VIRAL AGENTS
    DINAN, FJ
    BARDOS, TJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (05) : 569 - 572
  • [8] On the chemistry of 5-aryl-2-hydrazino-benzo[6,7]cyclohepta[1 2-b]pyrido[2,3-e]pyrimidin-4-one
    El-Gazzar, A. B. A.
    Abu-Zied, Kh. M.
    El-Din, N. Khir
    [J]. HETEROATOM CHEMISTRY, 2007, 18 (01) : 34 - 43
  • [9] Synthesis and Antioxidant, Anti-Inflammatory, and Analgesic Activity of Novel Polycyclic Pyrimido[4,5-b]quinolines
    El-Gazzar, A. B. A.
    Hafez, H. N.
    Abu-Hashem, A. A.
    Aly, A. S.
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (02) : 379 - 405
  • [10] New acyclic nucleosides analogues as potential analgesic, anti-inflammatory, anti-oxidant and anti-microbial derived from pyrimido[4,5-b]quinolines
    El-Gazzar, A. B. A.
    Hafez, H. N.
    Nawwar, G. A. M.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (04) : 1427 - 1436
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