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

被引：14

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

来源：

JOURNAL OF THE SERBIAN CHEMICAL SOCIETY | 2016年 / 81卷 / 02期

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

页码：133 / 140

页数：8

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 [J].

Bencini, Andrea ;

Lippolis, Vito .

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 [J].

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 .

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 [J].

Carta, Antonio ;

Loriga, Mario ;

Paglietti, Giuseppe ;

Ferrone, Marco ;

Fermeglia, Maurizio ;

Pricl, Sabrina ;

Sanna, Tiziana ;

Ibba, Cristina ;

La Colla, Paolo ;

Loddo, Roberta .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (05) :1914-1927

[6] Synthesis, biological evaluation and SAR study of novel pyrazole analogues as inhibitors of Mycobacterium tuberculosis [J].

Castagnolo, Daniele ;

De Logu, Alessandro ;

Radi, Marco ;

Bechi, Beatrice ;

Manetti, Fabrizio ;

Magnani, Matteo ;

Supino, Sibilla ;

Meleddu, Rita ;

Chisu, Lorenza ;

Botta, Maurizio .

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 [J].

CHVAPIL, M ;

HURYCH, J ;

EHRLICHOVA, E ;

CMUCHALOVA, B .

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 [J].

CHVAPIL, M ;

HURYCH, J ;

EHRLICHOVA, E ;

TICHY, M .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1967, 2 (02) :229-+

[10]

Danac R, 2005, REV CHIM-BUCHAREST, V56, P85

← 1 2 3 4 →