Synthesis and Biological Activity of (Z) -n-(5-Benzylidene-4-oxo-2-substituted-phenylthiazolidin-3-yl)-5-((1, 3-dioxoisoindolin-2-yl)methyl)-2-hydroxybenzamide

被引:0
|
作者
Patel, M. C. [1 ]
Dhameliya [1 ]
机构
[1] PS Sci & HD Patel Arts Coll, Kadi, Gujarat, India
关键词
5-((1,3-Dioxoisoindolin-2-yl)methyl-2-hydroxybenzohydrazide; Thiazolidin; Antibacterial activity; ANTIMICROBIAL ACTIVITY; ANTICANCER; DISCOVERY; HYDRAZIDE; RESISTANT;
D O I
10.1155/2010/586984
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
5-((1, 3-Dioxoisoindolin-2-yl)methyl-2-hydroxybenzohydrazide (1) undergoes facile condensation with aromatic aldehydes to afford the corresponding N'-substituted-phenyl-5-((1,3-dioxoisoindolin-2-yl)methyl)-2-hydroxybenzohydrazide (2a-h) in good yields. Cyclocondensation of compounds (2a-h) with thioglycolic acid yields 5-((1,3-dioxoisoindolin-2-yl) methyl)-2-hydroxy-N-(4-oxo-2-substituted phenylthiazolidin-3-yl)benzamide (3a-h). These (3a-h) compounds were further reacted with benzaldehyde in the presence of sodium ethanolate affords, (Z) -N-(5-benzylidene-4-oxo-2-substituted phenylthiazolidin-3-yl)-5-((1,3-dioxoisoindolin-2-yl) methyl)-2-hydroxybenzamide(4a-h). The structures of these compounds were established on the basis of analytical and spectral data. All the newly synthesized compounds were evaluated for their antibacterial and antifungal activities.
引用
收藏
页码:1484 / 1490
页数:7
相关论文
共 50 条
  • [1] Design and synthesis of 2-(1, 3-dioxoisoindolin-2-yl)-N-(4-oxo-2-substitutedthiazolidin-3-yl) acetamide derivatives as potential anticonvulsant agents
    Nikalje, Anna Pratima G.
    Khan, Firoz Kalam
    Ghodke, Mangesh
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (11) : 5448 - 5455
  • [2] Synthesis and biological activity of N-[5-(pyrid-4-yl)-1,3,4-thiadiazol-2-yl]-N′-aroylureas
    Song, XJ
    Feng, GR
    Chen, CB
    Zhang, ZW
    Wang, YG
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2005, 25 (12) : 1587 - 1590
  • [3] N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-hydroxybenzamide
    Wang, Qing-Hua
    Guo, Guo-Cong
    Cai, Li-Zhen
    Guo, Hong-Xu
    Chen, Ming-Li
    Weng, Wen
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O4802 - U5928
  • [4] (Z)-3α-(1,3-Dioxoisoindolin-2-yl)-17(20)-pregnene
    Qi, Yue
    Qin, Nan
    Duan, Hong-Quan
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2065 - U793
  • [5] (E)-Methyl 2-[(1,3-dioxoisoindolin-2-yl)methyl]-3-phenylacrylate
    Lakshmanan, D.
    Murugavel, S.
    Kannan, D.
    Bakthadoss, M.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O2219 - +
  • [6] Synthesis and antimicrobial activity of N-[(α-methyl)benzylidene]-(3-substituted-1,2,4-triazol-5-yl-thio) acetohydrazides
    Ersan, S
    Nacak, S
    Berkem, R
    FARMACO, 1998, 53 (12): : 773 - 776
  • [7] SYNTHESIS AND ANTI-INFLAMMATORY EVALUATION OF 2-(3-(2-(1,3-DIOXOISOINDOLIN-2-YL) ACETAMIDO)-4-OXO-2-SUBSTITUTED THIAZOLIDIN-5-YL) ACETIC ACID DERIVATIVES
    Nikalje, Anna Pratima G.
    Hirani, Nazma
    Shaikh, Sameer, I
    Nawle, R.
    Une, Hemant D.
    18TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY, 2014,
  • [8] Synthesis of new 3-(substituted phenacyl)-5-[3′-(4H-4-oxo-1-benzopyran-2-yl)-benzylidene]-2,4-thiazolidinediones and their antimicrobial activity
    Tuncbilek, M
    Altanlar, N
    ARCHIV DER PHARMAZIE, 2006, 339 (04) : 213 - 216
  • [9] Synthesis of Substituted -N-(5-((7-Methyl-2-Oxo-2H-Chromen-4-yl)-Methyl)-1,3,4-Thiadiazol-2-yl)-Benzamide Derivatives Using TBTU as Coupling Agent and their Evaluation for Anti Tubercular Activity
    Kakadiya, Monika
    Pasha, Yunus
    Noolvi, Malleshappa
    Patel, Ashish
    LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (02) : 158 - 166
  • [10] SYNTHESIS AND ANTHELMINTIC ACTIVITY OF 1-(5'-SUBSTITUTED PHENOXY METHYL, 1',3',4'-THIADIAZOL-2'-YL), 2-METHYL-4-SUBSTITUTED BENZYLIDENE IMIDAZOL-5-ONES
    SHUKLA, JS
    AGARWAL, K
    CURRENT SCIENCE, 1982, 51 (17): : 817 - 820