Synthesis and evaluation of 2-(4-methoxy-2-oxo-1-phenyl/methyl-1, 2-dihydroquinolin-3-yl)-2-methyl-3-(phenyl/substitutedphenyl-amino)thiazolidin-4-one as antibacterial and anticancer agents

被引:0
|
作者
Reis, Maria de Graca [1 ]
Desai, Shivlingrao Mamle [1 ]
Naik, Soniya [1 ]
Fernandes, Jairus [1 ]
Tari, Prassad [1 ]
机构
[1] PESs Rajaram & Tarabai Bandekar Coll Pharm, Dept Pharmaceut Chem, Ponda 403401, Goa, India
关键词
Thiazolidinone; quinolin-2-one; anticancer; antibacterial; human lung carcinoma;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 2-(4-methoxy-2-oxo-1-phenyl/methyl-1,2-dihydroquinolin-3-yl)-2-methyl-3-(phenyl/substitutedphenylamino) thiazolidin-4-one derivatives (III-a(1-5) / III-b(1-5) have been synthesized by appropriate synthetic route and satisfactorily characterized by UV-Vis, IR, NMR and mass spectral data. All synthesized compounds have been evaluated for their in vitro antibacterial and anticancer activity. Compounds have been evaluated against two Gram positive strains (Staphylococcus aureus and Bacillus subtilis) and two Gram negative strains (Escherichia coli and Pseudomonas aeruginosa). Compound III-a2 with R-1 = C6H5 and R-2 = Cl shows promising activity against all bacterial strains with MIC between 0.25 and 4 mu g/mL. Ciprofloxacin is used as the reference standard. The compounds have also been screened for their anticancer activity against A549-human lung carcinoma cell line. Compound III-a2 (IC50 square 10 mu g) with R-1 = C6H5 and R-2 = Cl, III-a5 (IC50 = 10 mu g) with R-1 = C6H5 and R-2 = CH3 and III-b2 (IC50 = 10 mu g) with R-1 = CH3 and R-2 = Cl show 100% cell death.
引用
收藏
页码:1254 / 1258
页数:5
相关论文
共 50 条
  • [21] 2-(4-Oxo-3-phenyl-1,3-thiazolidin-2-yl-idene)malononitrile
    Sakka, Ola K.
    Fleita, Daisy H.
    Harrison, William T. A.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O350 - +
  • [22] Methyl 2-{[(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-ylidene)(thiophen-2-yl)methyl]amino}-3-phenylpropionate
    Zhu, Hualing
    Zhao, Xinxin
    Wang, Zhan
    Ren, Junjie
    Zhang, Miao
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2200 - U2010
  • [23] 2-[1-({2-[1-(2-Hydroxy-5-{[methyl(phenyl)amino]methyl}phenyl)ethylideneamino]ethyl}imino)ethyl]-4-{[methyl(phenyl)amino]methyl}phenol
    Ourari, Ali
    Ouennoughi, Yasmina
    Bouacida, Sofiane
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1562 - +
  • [24] 2-({[4-(1,3-Benzothiazol-2-yl)phenyl]amino}methyl)phenol
    Potgieter, Kim
    Gerber, Thomas
    Hosten, Eric
    Betz, Richard
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68 : O27 - +
  • [25] Synthesis and reactions of 2-amino-6-(3-methyl-5-oxo-1-phenyl-2-pyrazolin-4-yl)-4-phenylpyridine-3-carbonitrile
    Ahmed, RA
    Kandeel, MM
    Abbady, MS
    Youssef, MSK
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (02) : 309 - 314
  • [26] Crystallographic and conformational analysis of 2-methyl-3-(2-nitro-phenyl)-4-phenyl-[1,2,4]oxadiazolidin-5-one
    Hasan Karabıyık
    Muhittin Aygün
    Necdet Coşkun
    Canan Kazak
    Journal of Chemical Crystallography, 2005, 35 : 577 - 582
  • [27] 4-Methyl-N-{2-[(E)-3-oxo-3-phenylprop1-en-1-yl]phenyl}benzenesulfonamide
    Kim, Sung-Gon
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2014, 70 : O851 - +
  • [28] Crystallographic and conformational analysis of 2-methyl-3-(2-nitro-phenyl)-4-phenyl-[1,2,4]oxadiazolidin-5-one
    Karabiyik, H
    Aygün, M
    Coskun, N
    Kazak, C
    JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2005, 35 (08) : 577 - 582
  • [29] SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF [6′-METHYL-4′-METHOXY-2-OXO-2H-[1]-BENZOPYRAN)-2",4"-DIHYDRO-[1", 2", 4"]-TRIAZOL-3"-ONE AND 3"-PHENYL-THIAZOLIDIN-4"-ONE-PHENOXYMETHYL DERIVATIVES OF DIPYRANOQUINOLINE
    Mulwad, V. V.
    Langi, B. P.
    Chaskar, J.
    Chaskar, A.
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2011, 45 (07) : 427 - 432
  • [30] Methyl 2-{[3-(4-nitrophenyl)-1,2,4-oxadiazol-5-yl]methoxy}-phenyl acetate
    Wang, HB
    Chen, JH
    Pu, YQ
    Wang, JT
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2004, 60 : O2073 - O2075