Antimicrobial and anticancer effects of some 2-(substitutedsulfanyl)-N-(5-methyl-isoxazol-3-yl)acetamide derivatives

被引:10
|
作者
Ozkay, Yusuf [1 ]
Incesu, Zerrin [2 ]
Onder, Nur Ipek [2 ]
Tunali, Yagmur [3 ]
Karaca, Hulya [3 ]
Isikdag, Ilhan [1 ]
Ucucu, Umit [1 ]
机构
[1] Anadolu Univ, Fac Pharm, Dept Pharmaceut Chem, TR-26470 Eskisehir, Turkey
[2] Anadolu Univ, Dept Biochem, Fac Pharm, TR-26470 Eskisehir, Turkey
[3] Anadolu Univ, Dept Pharmaceut Microbiol, Fac Pharm, TR-26470 Eskisehir, Turkey
关键词
Anticancer; Antibacterial; Antifungal; Isoxazole; Azole; HEAT-SHOCK PROTEINS; ANTIPROLIFERATIVE ACTIVITY; MINOR-GROOVE; DNA; COMPLEXES; DRUGS; BINDING; LIPOPHILICITY; INTERCALATION; RECOGNITION;
D O I
10.1007/s00044-012-0021-2
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
In the present study, some isoxazole-(benz)azole derivatives (3a-3j) were synthesized by considering antimicrobial and anticancer potencies of azole compounds. Chemical structures of obtained compounds (3a-3j) were confirmed by the data of spectral and elemental analyses. Anticancer activity evaluation was performed at two steps. Initially, cytotoxic effects of the compounds (3a-3j) on HT-29 (colon carcinoma) and C-6 (melanoma) cell lines were determined by MTT assay. Secondly, the compounds 3g-3i, which indicated significant cytotoxicity were selected and analysed for their inhibitory activity on DNA synthesis of carcinogenic cells. The compounds 3g and 3h showed notable DNA synthesis inhibition on both cancer cell lines. Antibacterial and antifungal activities of the synthesized compounds (3a-3j) were also examined. All of the compounds exhibited very poor antibacterial activity against gram negative and gram positive bacterial strains, whereas antifungal activity of the compounds 3a-3f was equal to that of Ketoconazole.
引用
收藏
页码:211 / 218
页数:8
相关论文
共 50 条
  • [1] Antimicrobial and anticancer effects of some 2-(substitutedsulfanyl)-N-(5-methyl-isoxazol-3-yl)acetamide derivatives
    Yusuf Özkay
    Zerrin İncesu
    Nur İpek Önder
    Yağmur Tunalı
    Hülya Karaca
    İlhan Işıkdağ
    Ümit Uçucu
    Medicinal Chemistry Research, 2013, 22 : 211 - 218
  • [2] The Inhibition of Carbon Steel Corrosion in Hydrochloric Acid Media Using 2-[(5-methyl-isoxazol-3-yl)-methyl]-benzimidazole
    Sebhaoui, J.
    El-Aoufir, Y.
    El-Bakri, Y.
    Bourazmi, H.
    Ben-Ali, A.
    Guenbour, A.
    Oudda, H.
    Zarrouk, A.
    Essassi, E. M.
    PORTUGALIAE ELECTROCHIMICA ACTA, 2021, 39 (03) : 213 - 224
  • [3] Synthesis of antifungal isoindole (5-methyl-isoxazole-3-yl)-[2-(5-methyl-isoxazol-3-yl) 2,3-dihydro-isoindol-1-ylidene]amine
    Al-Shihry, Shar S.
    MOLBANK, 2005, (06)
  • [4] QSRT STUDIES OF 2-(5-ARYL-1, 3, 4-OXADIAZOL-2-YL)-N-(5-METHYLISOXAZOL-3-YL)-ACETAMIDE DERIVATIVES AS AN ANTIMICROBIAL AGENTS
    Marri, Srinivas
    Kakkerla, Ramu
    Krishna, M. P. S. Murali
    INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH, 2019, 10 (12): : 5391 - 5396
  • [5] Synthesis and Crystal Structure of a New Schiff Base 4-[(2-hydroxy-benzylidene)-amino]-N-(5-methyl-isoxazol-3-yl)-benzenesulfonamide
    Subashini, Annamalai
    Hemamalini, Madhukar
    Muthiah, P. Thomas
    Bocelli, Gabriele
    Cantoni, Andrea
    JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2009, 39 (02) : 112 - 116
  • [6] Synthesis and Crystal Structure of a New Schiff Base 4-[(2-hydroxy-benzylidene)-amino]-N-(5-methyl-isoxazol-3-yl)-benzenesulfonamide
    Annamalai Subashini
    Madhukar Hemamalini
    P. Thomas Muthiah
    Gabriele Bocelli
    Andrea Cantoni
    Journal of Chemical Crystallography, 2009, 39 : 112 - 116
  • [7] 2-(4-Bromophenyl)-N-(5-methylpyridin-2-yl)acetamide
    Fun, Hoong-Kun
    Ooi, Chin Wei
    Nayak, Prakash S.
    Narayana, B.
    Sarojini, B. K.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : 02526 - +
  • [8] N-(5-Bromopyridin-2-yl)acetamide
    Fun, Hoong-Kun
    Shahani, Tara
    Kumar, Rajesha
    Isloor, Arun M.
    Shivananda, Kammasandra N.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2043 - U573
  • [9] N-(5-Benzylsulfanyl-1,3,4-thiadiazol-2-yl)-2-(piperidin-1-yl)acetamide
    Ismailova, D. S.
    Okmanov, R. Ya.
    Ziyaev, A. A.
    Shakhidoyatov, Kh. M.
    Tashkhodjaev, B.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2014, 70 : O241 - +
  • [10] Synthesis, reactions and characterization of 2-(2-methyl-5-nitro-1H-benzimidazol-1-yl)-N'-(arylmethylene)acetohydrazide and 2-(2-methyl-5-nitro-1H-benzimidazol-1-yl)-N-(4-oxo-2-aryl-1, 3-thiazolidin-3-yl) acetamide derivatives
    Ramla, Mostafa M.
    El Nazhawy, Ahmed O. H.
    Attaby, Fawzy A.
    AFINIDAD, 2006, 63 (526) : 488 - 494