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
  • [31] 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
    V. V. Mulwad
    B. P. Langi
    J. Chaskar
    A. Chaskar
    Pharmaceutical Chemistry Journal, 2011, 45 : 427 - 432
  • [32] (E)-2-Methyl-3-(phenethylamino)-1-phenyl-prop2-en-1-one
    Huang, SP
    Li, HT
    Shi, HP
    Tan, GF
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2006, 62 : O1541 - O1542
  • [33] Synthesis and Antimicrobial Activities of Novel Series of 3-(4-(2-substituted thiazol-4-yl)phenyl)-2-(4-methyl-2-substituted thiazol-5-yl) thiazolidin-4-one Derivatives
    Shelke, Shivaji H.
    Mhaske, Pravin C.
    Narkhade, Sachin
    Bobade, Vivek D.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (04) : 1151 - 1156
  • [34] (Z)-3-Phenyl-2-(propan-2-ylidenehydrazono)-thiazolidin-4-one
    Xu, LZ
    Li, K
    Song, HB
    Huang, YW
    Zhou, K
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O1417 - O1418
  • [35] Methyl {2-[(3-phenyl-1,2,4-oxadiazol-5-yl)methoxy]phenyl}acetate
    Wang, HB
    Chen, JH
    Wang, JT
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2004, 60 : O1478 - O1480
  • [36] Crystal structure of (2E)-1-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
    Kimpende, Peter Mangwala
    Ngoc Thanh Nguyen
    Minh Thao Nguyen
    Quoc Trung Vu
    Van Meervelt, Luc
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : 424 - +
  • [37] Ethyl 2-{2-[(1-methyl-2-phenyl-1H-indol-3-yl)diazenyl]thiazol-4-yl}acetate
    Seferoglu, Zeynel
    Hokelek, Tuncer
    Sahin, Ertan
    Saylam, Aytul
    Ertan, Nermin
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O5488 - O5489
  • [38] Synthesis, characterization and antibacterial activity of 2-[(substituted phenyl)]-3-[(2-methyl-4-thiazolyl)acetamido]-thiazolidin-4-ones
    Rao, GK
    Chakraborty, SP
    Pai, PNS
    Murty, MS
    ASIAN JOURNAL OF CHEMISTRY, 2005, 17 (03) : 2013 - 2015
  • [39] Ethyl 6-Methyl-2-oxo-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylate
    Goncalves, Itamar Luis
    de Azambuja, Gabriel Oliveira
    Davi, Leonardo
    Goncalves, Guilherme Arrache
    Kagami, Luciano Porto
    das Neves, Gustavo Machado
    Silveira, Joao Pedro
    Santos Canto, Romulo Faria
    Eifler-Lima, Vera Lucia
    MOLBANK, 2019, 2019 (03)
  • [40] Novel 3-(2-(3-methyl-5-substituted-phenyl-4,5-dihydropyrazol-1-yl)-2-oxoethoxy)-2-substituted-phenyl-4H-chromen-4-one: Synthesis and Anticancer Activity
    Liu, Xin-Hua
    Li, Jun
    Wu, Fan-Rong
    Song, Bao-An
    Bhadury, Pinaki S.
    Shi, Lei
    MEDICINAL CHEMISTRY, 2011, 7 (06) : 605 - 610