Synthesis and Anti-mycobacterial Activities of Heterocyclic Hydrazones and Their Bioisosteric Compounds

被引：0
|
作者：
Li, Zhongzhou [1 ]
Zhao, Sheng [1 ]
Li, Xinjun [1 ]
Wang, Cuicui [1 ]
Yao, Lulu [1 ]
Jin, Ruiliang [2 ]
Zou, Xinzhou [1 ]
机构：
[1] E China Normal Univ, Dept Chem, Shanghai 200241, Peoples R China
[2] Tongji Univ, Shanghai Key Lab TB, Shanghai Pulm Hosp, Shanghai 200433, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 35卷 / 06期
关键词：
heterocyclic hydrazone analogs; synthesis; Mycobacterium tuberculosis; anti-mycobacterial activity; ANALOGS; MYCOBACTERIA; CURCUMIN; DESIGN; SERIES;
D O I：
10.6023/cjoc201412011
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A total of 22 new heterocyclic hydrazones and their bioisosteric compounds were synthesized and evaluated for their activity against Mycobacterium tuberculosis, strain H37Rv. All newly synthesized compounds showed inhibitory activities. Among these compounds, (1E,4E)-1,5-bis(5-bromo-2-thiophenyl)-1,4-pentadiene-3-one-(1,4,5,6-tetrahydro-2-pyrimidimyl)-hydrazone (1d) showed the most effective anti-tubercular activity with MIC90 value of 2 mu g/mL, and exhibited an excellent inhibitory activity against isoniazid-resistant strain 242, multidrug-resistant strain 2312, and extensively drug-resistant strain 1220 with MIC90 values of 0.25, 1.0 and 0.5 mu g/mL, respectively.
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页码：1310 / 1319
页数：10
相关论文
共 41 条
  • [1] Synthesis and antimycobacterial evaluation of 3a,4-dihydro-3H-indeno [1,2-c] pyrazole-2-carboxamide analogues
    Ahsan, Mohamed Jawed
    Samy, Jeyabalan Govinda
    Khalilullah, Habibullah
    Bakht, Mohamed Afroz
    Hassan, Mohd. Zaheen
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (11) : 5694 - 5697
  • [2] [Anonymous], 2007, CHEM HETEROCYCL COMP, DOI DOI 10.1007/S10593-007-0154-2
  • [3] ACETYLATION AND S-ALKYLATION OF ETHYLENE THIOUREA
    BAER, JE
    LOCKWOOD, RG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (04) : 1162 - 1164
  • [4] Bo Z.-S., 2004, RES DEV NEW HETEROCY, P179
  • [5] CHARACTERIZATION OF ALKYL HALIDES BY USE OF ETHYLENETHIOUREA
    BOYD, RN
    MEADOW, M
    [J]. ANALYTICAL CHEMISTRY, 1960, 32 (04) : 551 - 554
  • [6] Chen SJ, 2011, CHINESE J ORG CHEM, V31, P187
  • [7] DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS
    COREY, EJ
    CHAYKOVSKY, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) : 1353 - +
  • [8] Synthesis of 1-[3-(4-benzotriazol-1/2-yl-3-fluoro-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-3-substituted-thiourea derivatives as antituberculosis agents
    Dixit, PP
    Patil, VJ
    Nair, PS
    Jain, S
    Sinha, N
    Arora, SK
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (03) : 423 - 428
  • [9] PREPARATION AND ISOMERIZATION OF 5-ALKYLAMINOTETRAZOLES
    FINNEGAN, WG
    HENRY, RA
    LIEBER, E
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (07) : 779 - 791
  • [10] Highly Selective Claisen-Schmidt Condensation Catalyzed by Silica Chloride Under Solvent-Free Reaction Conditions
    Hazarkhani, Hassan
    Kumar, Pradeep
    Kondiram, Kadam Sachin
    Gadwal, Ikhlas M. Shafi
    [J]. SYNTHETIC COMMUNICATIONS, 2010, 40 (19) : 2887 - 2896
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