Solvent dependent selective alkylation of a bis(sulfonamide) for the synthesis of a DNA-binding chiral polyamine

被引：7
作者：
Peña, C
Alfonso, I
Voelcker, NH
Gotor, V
机构：
[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain
[2] Univ Jaume 1, ESTCE, Dept Quim Inorgan & Organ, E-12071 Castellon de La Plana, Spain
[3] Flinders Univ S Australia, Sch Chem Phys & Earth Sci, Bedford Pk, SA 5042, Australia
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 16期
基金：
澳大利亚研究理事会;
关键词：
cyclohexane-1,2-diamine; bis-sulfonamide; chiral polyamines; DNA-binding;
D O I：
10.1016/j.tetlet.2005.02.141
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new optically active linear polyamine has been efficiently prepared and its DNA binding abilities studied by UV melting experiments. The key step for this synthesis was the selective monoalkylation of the corresponding bis(sulfonamide). Thus, it is possible to obtain mono or dialkylated compounds by simply changing the reaction conditions. These results are explained in terms of conformational preferences and solvophobic effects. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2783 / 2787
页数：5
相关论文
共 41 条
  • [1] Alfonso I, 2000, CHEM-EUR J, V6, P3331, DOI 10.1002/1521-3765(20000915)6:18<3331::AID-CHEM3331>3.0.CO
  • [2] 2-8
  • [3] Alfonso I, 2001, HELV CHIM ACTA, V84, P280, DOI 10.1002/1522-2675(20010228)84:2<280::AID-HLCA280>3.3.CO
  • [4] 2-F
  • [5] Chemoenzymatic syntheses of two optically active hexa-azamacrocycles
    Alfonso, I
    Rebolledo, F
    Gotor, V
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (02) : 367 - 374
  • [6] [Anonymous], 1989, NUCL OVERHAUSER EFFE, DOI DOI 10.1002/MRC.1260280819
  • [7] THE LOW-TEMPERATURE CRYSTAL-STRUCTURE OF THE PURE-SPERMINE FORM OF Z-DNA REVEALS BINDING OF A SPERMINE MOLECULE IN THE MINOR-GROOVE
    BANCROFT, D
    WILLIAMS, LD
    RICH, A
    EGLI, M
    [J]. BIOCHEMISTRY, 1994, 33 (05) : 1073 - 1086
  • [8] Efficient macrocyclization of U-turn preorganized peptidomimetics:: The role of intramolecular H-bond and solvophobic effects
    Becerril, J
    Bolte, M
    Burguete, MI
    Galindo, F
    García-España, E
    Luis, SV
    Miravet, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) : 6677 - 6686
  • [9] The mono-functionalization of symmetrical polyamines
    Bender, JA
    Meanwell, NA
    Wang, T
    [J]. TETRAHEDRON, 2002, 58 (16) : 3111 - 3128
  • [10] METHODS FOR THE SELECTIVE MODIFICATION OF SPERMIDINE AND ITS HOMOLOGS
    BERGERON, RJ
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (04) : 105 - 113
12345