Design, synthesis and antimycobacterial evaluation of some new azaheterocycles with the 4,7-phenanthroline skeleton. Part VI

被引:13
作者
Al Matarneh, Cristina M. [1 ]
Ciobanu, Catalina I. [2 ]
Mangalagiu, Ionel I. [1 ]
Danac, Ramona [1 ]
机构
[1] Alexandru Ioan Cuza Univ, Fac Chem, Dept Chem, 11 Carol 1, Iasi 700506, Romania
[2] Alexandru Ioan Cuza Univ, Fac Chem, Res Dept, 11 Carol 1, Iasi 700506, Romania
基金
美国国家卫生研究院;
关键词
p-halogenobenzoyl; cycloimmonium salts; antimycobacterial; 4,7-phenanthroline; N-alkylation; PROLINE HYDROXYLATION; BIOLOGICAL-ACTIVITIES; CHELATING-AGENTS; DERIVATIVES; ANALOGS; 1,10-PHENANTHROLINE;
D O I
10.2298/JSC150514084A
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A feasibility study concerning the synthesis, structure and in vitro antimycobacterial evaluation of new 4,7-phenanthroline derivatives is reported. The preparation is straightforward and efficient, involving an N-alkylation reaction of 4,7-phenanthroline. The structure of the new compounds were verified by elemental and spectral (IR, H-1-and C-13-NMR) analysis. The in vitro antimycobacterial evaluation of the five synthesized compounds was investigated against Mycobacterium tuberculosis H37Rv under aerobic conditions. A certain influence of substituents on the para position of the benzoyl moiety was observed; the 4,7-phenanthrolin-4-ium salt substituted with p-chlorobenzoyl group showing the most pronounced antimycobacterial activity.
引用
收藏
页码:133 / 140
页数:8
相关论文
共 38 条
  • [1] Beauchamp DA, 2002, CHEM-EUR J, V8, P5084, DOI 10.1002/1521-3765(20021115)8:22<5084::AID-CHEM5084>3.0.CO
  • [2] 2-8
  • [3] 1,10-Phenanthroline: A versatile building block for the construction of ligands for various purposes
    Bencini, Andrea
    Lippolis, Vito
    [J]. COORDINATION CHEMISTRY REVIEWS, 2010, 254 (17-18) : 2096 - 2180
  • [4] Sensitive Detection of Gene Expression in Mycobacteria under Replicating and Non-Replicating Conditions Using Optimized Far-Red Reporters
    Carroll, Paul
    Schreuder, Lise J.
    Muwanguzi-Karugaba, Julian
    Wiles, Siouxsie
    Robertson, Brian D.
    Ripoll, Jorge
    Ward, Theresa H.
    Bancroft, Gregory J.
    Schaible, Ulrich E.
    Parish, Tanya
    [J]. PLOS ONE, 2010, 5 (03):
  • [5] Design, synthesis, and preliminary in vitro and in silico antiviral activity of [4,7]phenantrolines and 1-oxo-1,4-dihydro-[4,7]phenantrolines against single-stranded positive-sense RNA genome viruses
    Carta, Antonio
    Loriga, Mario
    Paglietti, Giuseppe
    Ferrone, Marco
    Fermeglia, Maurizio
    Pricl, Sabrina
    Sanna, Tiziana
    Ibba, Cristina
    La Colla, Paolo
    Loddo, Roberta
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (05) : 1914 - 1927
  • [6] Synthesis, biological evaluation and SAR study of novel pyrazole analogues as inhibitors of Mycobacterium tuberculosis
    Castagnolo, Daniele
    De Logu, Alessandro
    Radi, Marco
    Bechi, Beatrice
    Manetti, Fabrizio
    Magnani, Matteo
    Supino, Sibilla
    Meleddu, Rita
    Chisu, Lorenza
    Botta, Maurizio
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (18) : 8587 - 8591
  • [7] Chu DQ, 2001, EUR J INORG CHEM, P1135
  • [8] EFFECTS OF VARIOUS CHELATING AGENTS QUINONES DIAZOHETEROCYCLIC COMPOUNDS AND OTHER SUBSTANCES ON PROLINE HYDROXYLATION AND SYNTHESIS OF COLLAGENOUS AND NON-COLLAGENOUS PROTEINS
    CHVAPIL, M
    HURYCH, J
    EHRLICHOVA, E
    CMUCHALOVA, B
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA, 1967, 140 (02) : 339 - +
  • [9] MECHANISM OF ACTION OF CHELATING AGENTS ON PROLINE HYDROXYLATION AND ITS INCORPORATION INTO COLLAGENOUS AND NON-COLLAGENOUS PROTEINS
    CHVAPIL, M
    HURYCH, J
    EHRLICHOVA, E
    TICHY, M
    [J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1967, 2 (02): : 229 - +
  • [10] Danac R, 2005, REV CHIM-BUCHAREST, V56, P85