SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF ACETOXYBENZOYL THIOUREAS WITH ARYL AND AMINO ACID SIDE CHAINS

被引:22
作者
Ngaini, Zainab [1 ]
Arif, Maya Asyikin Mohd [1 ]
Hussain, Hasnain [2 ]
Mei, Er Su [1 ]
Tang, Donna [1 ]
Kamaluddin, Dyg Halimatulzahrah Abang [1 ]
机构
[1] Univ Malaysia Sarawak, Dept Chem, Fac Resource Sci & Technol, Kota Samarahan 94300, Sarawak, Malaysia
[2] Univ Malaysia Sarawak, Dept Mol Biol, Fac Resource Sci & Technol, Kota Samarahan 94300, Sarawak, Malaysia
关键词
Thiourea; aspirin; amino acid; antibacterial activity; DERIVATIVES; ASPIRIN;
D O I
10.1080/10426507.2011.562398
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of acetoxybenzoylthioureas derivatives with aryl and amino acid ester side chains were prepared by reaction of acetoxybenzoyl isothiocyanate, an acyloxy benzyl ester-based derivative of aspirin, with aryl amines or amino-functionalized amino acids with overall yields of 46-73%. The products that display a thiourea segment as a linker showed improved antibacterial properties in comparison with aspirin. The structures of the synthesized compounds were characterized by infra red spectroscopy, C-13 nuclear magnetic resonance (NMR), and H-1 NMR spectroscopy. The compounds were screened for their antibacterial activity by using gram-negative bacteria (E. coli ATCC 8739). [2-(phenylcarbamothioylcarbamoyl)phenyl] acetate showed the highest antibacterial activity against E. coli compared with other synthesized compounds.
引用
收藏
页码:1 / 7
页数:7
相关论文
共 12 条
  • [1] Campo Del R., 2004, J INORG BIOCHEM, V98, P1307
  • [2] SOME PHENYLTHIOUREA DERIVATIVES AND THEIR ANTITUBERCULOUS ACTIVITY
    DOUB, L
    RICHARDSON, LM
    HERBST, DR
    BLACK, ML
    STEVENSON, OL
    BAMBAS, LL
    YOUMANS, GP
    YOUMANS, AS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (09) : 2205 - 2217
  • [3] Characteristics of cyanopindolol analogues active at the beta(3)-adrenoceptor in rat ileum
    Hoey, AJ
    Jackson, CM
    Pegg, GG
    Sillence, MN
    [J]. BRITISH JOURNAL OF PHARMACOLOGY, 1996, 119 (03) : 564 - 568
  • [4] Searching for new NO-donor aspirin-like molecules: A new class of nitrooxy-acyl derivatives of salicylic acid
    Lazzarato, Loretta
    Donnola, Monica
    Rolando, Barbara
    Marini, Elisabetta
    Cena, Clara
    Coruzzi, Gabriella
    Guaita, Elena
    Morini, Giuseppina
    Fruttero, Roberta
    Gasco, Alberto
    Biondi, Stefano
    Ongini, Ennio
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (06) : 1894 - 1903
  • [5] MADAN VK, 1991, J INDIAN CHEM SOC, V68, P471
  • [6] PAPPANO N B, 1985, Revista Argentina de Microbiologia, V17, P27
  • [7] Synthesis, structural characterization and in vitro cytotoxicity and anti-bacterial activity of some copper(I) complexes with N,N′-disubstituted thioureas
    Rauf, M. Khawar
    Imtiaz-ud-Din
    Badshah, Amin
    Gielen, Marcel
    Ebihara, Masahiro
    de Vos, Dick
    Ahmed, Safeer
    [J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 2009, 103 (08) : 1135 - 1144
  • [8] The use of nitric oxide-donating nonsteroidal anti-inflammatory drugs in the chemoprevention of colorectal neoplasia
    Rigas, Basil
    [J]. CURRENT OPINION IN GASTROENTEROLOGY, 2007, 23 (01) : 55 - 59
  • [9] Thiourea, triazole and thiadiazine compounds and their metal complexes as antifungal agents
    Rodríguez-Fernández, E
    Manzano, JL
    Benito, JJ
    Hermosa, R
    Monte, E
    Criado, JJ
    [J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 2005, 99 (08) : 1558 - 1572
  • [10] Wei T., 2010, Chem. Abstr., V153, Patent No. 101735129