Synthesis and biological activity of novel 1H-1,4-diazepines containing benzene sulfonyl piperazine moiety

被引:11
|
作者
Saingar, Shalini [1 ]
Kumar, Rajesh [2 ]
Joshi, Yogesh Chandra [1 ]
机构
[1] Univ Rajasthan, Dept Chem, Jaipur 302004, Rajasthan, India
[2] Def Lab, Jodhpur 342011, Rajasthan, India
关键词
1H-1,4-diazepines; beta-Diketones/beta-ketoesters; Piperazine; Silica sulphuric acid; Ethylenediamine; Biological activities; PLATELET-ACTIVATING-FACTOR; DRUG-RESISTANT STRAINS; STAPHYLOCOCCUS-AUREUS; DERIVATIVES; ANTAGONISTS; DESIGN; POTENT; 1,4-DIAZEPINES; ANTIFUNGAL; AGENTS;
D O I
10.1007/s00044-010-9430-2
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The synthesis of biologically active 1H-1,4-diazepines 6a-e in good yield, from the heterocyclization reaction of [N (4)-(4-acetylamino) benzene sulfonyl) piperazinyl-N (1)-propyl]-1,3-dialkyl/aryl propane-1,3-dione 5a-e and ethylenediamine (EDA) in the presence of silica sulphuric acid (SSA) is described. The novel beta-diketones/beta-ketoesters 5a-e were synthesized by the condensation reaction of [N (4)-(4-acetylamino) benzene sulfonyl) piperazinyl-N (1)-1-bromopropane with various beta-diketones/beta-ketoesters 4a-e. All structures of the newly synthesized compounds were elucidated by elemental analysis and spectral studies. The compounds 6a-e have been screened for antimicrobial, antifungal and anthelmintic activity.
引用
收藏
页码:975 / 980
页数:6
相关论文
共 50 条
  • [1] Synthesis and biological activity of novel 1H-1,4-diazepines containing benzene sulfonyl piperazine moiety
    Shalini Saingar
    Rajesh Kumar
    Yogesh Chandra Joshi
    Medicinal Chemistry Research, 2011, 20 : 975 - 980
  • [2] Synthesis, antimicrobial and antifungal activities of novel 1H-1,4-diazepines containing pyrazolopyrimidinone moiety
    Rajesh Kumar
    Yogesh Chandra Joshi
    Journal of Chemical Sciences, 2009, 121 : 497 - 502
  • [3] Synthesis, antimicrobial and antifungal activities of novel 1H-1,4-diazepines containing pyrazolopyrimidinone moiety
    Kumar, Rajesh
    Joshi, Yogesh Chandra
    JOURNAL OF CHEMICAL SCIENCES, 2009, 121 (04) : 497 - 502
  • [4] 1,4-Diazepines: A Review on Synthesis, Reactions and Biological Significance
    Rashid, Muhammad A.
    Ashraf, Aisha
    Rehman, Sahibzada S.
    Shahid, Shaukat A.
    Mahmood, Adeel
    Faruq, Muhammad
    CURRENT ORGANIC SYNTHESIS, 2019, 16 (05) : 709 - 729
  • [5] Synthesis of new 1H-1,4-diazepines from new β-diketones/β-ketoesters and their antimicrobial, antifungal and anthelmintic activities
    Kumar, Rajesh
    Joshi, Y. C.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 17 (03) : 291 - 292
  • [6] Synthesis and DNA strand breakage activity of some 1,4-diazepines
    Mibu, N
    Yukawa, M
    Kashige, N
    Iwase, Y
    Goto, Y
    Miake, F
    Yamaguchi, T
    Ito, S
    Sumoto, K
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (01) : 27 - 31
  • [7] Synthesis and Biological Activity of Novel N-glucosides Containing Substituted Piperazine Moiety
    Zhang, Li-Yuan
    Wang, Bao-Lei
    Zhan, Yi-Zhou
    Hua, Xue-Wen
    Liu, Ming
    Zhang, Xiao
    Song, Hai-Bin
    Li, Zheng-Ming
    LETTERS IN DRUG DESIGN & DISCOVERY, 2016, 13 (04) : 343 - 351
  • [8] STUDIES ON DIAZEPINES .25. SYNTHESES OF FULLY UNSATURATED 1,4-OXAZEPINES AND 1H-1,4-DIAZEPINES USING PHOTOCHEMICAL VALENCE ISOMERIZATION OF TRICYCLOHEPTENE SYSTEMS
    KURITA, J
    IWATA, K
    TSUCHIYA, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1987, 35 (08) : 3166 - 3174
  • [9] Synthesis, spectral studies and biological activity of novel 1H-1,4-diazepine derivatives
    Kumar, Rajesh
    Joshi, Yogesh C.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2010, 49 (01): : 84 - 88
  • [10] Structure-based design, synthesis, and biological evaluation of novel 1,4-diazepines as HDM2 antagonists
    Raboisson, P
    Marugán, JJ
    Schubert, C
    Koblish, HK
    Lu, TB
    Zhao, SY
    Player, MR
    Maroney, AC
    Reed, RL
    Huebert, ND
    Lattanze, J
    Parks, DJ
    Cummings, MD
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (07) : 1857 - 1861