Quinoxaline 1,4-dioxide: A versatile scaffold endowed with manifold activities

被引:141
作者
Carta, A [1 ]
Corona, P [1 ]
Loriga, M [1 ]
机构
[1] Univ Sassari, Fac Farm, Dipartimento Farmacochim Tossicol, I-07100 Sassari, Italy
关键词
quinoxaline 1,4-dioxides; animal growth promoting; antibacterial activity; hypoxia-selective activity; mutagenicity; antimycobacterial activity; anticandida activity; antiprotozoal activity; SAR studies; chemical syntheses and reactions;
D O I
10.2174/0929867054864831
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
Since 1940s, Quinoxaline 1,4-dioxides (QdNO's) are known as potent antibacterial agents, and subtherapeutic levels have been used to promote growth and improve efficiency of feed conversion in animal feed. They have also shown a selective cytotoxicity against hypoxic cells present in solid tumours. Furthermore, recent studies have put in evidence that QdNO's are endowed with antitubercular, antiprotozoal and anticandida activities. On the other hand, several authors have reported about photoallergic and mutagenic effects of some derivatives. QdNO's may also cause the development of antibiotic-resistant bacteria and influence the horizontal transfer of virulence genes between bacteria. In this review article we report the biological properties, the mode of action and Structure Activity Relationship (SAR) studies of the QdNO derivatives. Furthermore, some cytogenetic and genotoxic effects, classical and more recent method of synthesis, the quinoxaline 1,4-dioxides, and some of their most important reactions, were also reported.
引用
收藏
页码:2259 / 2272
页数:14
相关论文
共 189 条
  • [11] MUTAGENICITY OF QUINDOXIN, ITS METABOLITES, AND 2 SUBSTITUTED QUINOXALINE-DI-N-OXIDES
    BEUTIN, L
    PRELLER, E
    KOWALSKI, B
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1981, 20 (03) : 336 - 343
  • [12] SILYLENAMINES AS SYNTHONS FOR SILYLATED HETEROCYCLES
    BIRKOFER, L
    QUITTMANN, W
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (01): : 257 - 268
  • [13] BORAH HN, 1984, TETRAHEDRON, V40, P1617, DOI 10.1016/S0040-4020(01)91814-9
  • [14] BORAH HN, 1984, HETEROCYCLES, V22, P2323
  • [15] BROWN DJ, 2004, HETEROCYCLES COMP S2
  • [16] Brown JM, 1999, CANCER RES, V59, P5863
  • [17] Calnan C D, 1975, Contact Dermatitis, V1, P384, DOI 10.1111/j.1600-0536.1975.tb05480.x
  • [18] Role of HIF-1α or in hypoxia-mediated apoptosis, cell proliferation and tumour angiogenesis
    Carmeliet, P
    Dor, Y
    Herbert, JM
    Fukumura, D
    Brusselmans, K
    Dewerchin, M
    Neeman, M
    Bono, F
    Abramovitch, R
    Maxwell, P
    Koch, CJ
    Ratcliffe, P
    Moons, L
    Jain, RK
    Collen, D
    Keshet, E
    [J]. NATURE, 1998, 394 (6692) : 485 - 490
  • [19] Synthesis, anti-mycobacterial, anti-trichomonas and anti-candida in vitro activities of 2-substituted-6,7-difluoro-3-methylquinoxaline 1,4-dioxides
    Carta, A
    Loriga, M
    Paglietti, G
    Mattana, A
    Fiori, PL
    Mollicotti, P
    Sechi, L
    Zanetti, S
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (02) : 195 - 203
  • [20] Novel substituted quinoxaline 1,4-dioxides with in vitro antimycobacterial and anticandida activity
    Carta, A
    Paglietti, G
    Nikookar, MER
    Sanna, P
    Sechi, L
    Zanetti, S
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2002, 37 (05) : 355 - 366