Synthesis of novel menthol derivatives containing 1,2,3-triazole group and their in vitro antibacterial activities

被引:0
|
作者
Karbasi, Mohadeseh [1 ]
Salehi, Peyman [1 ]
Aliahmadi, Atousa [2 ]
Bararjanian, Morteza [1 ]
Zandi, Farzaneh [2 ]
机构
[1] Shahid Beheshti Univ, Med Plants & Drugs Res Inst, Dept Phytochem, GC, Tehran 1983963113, Iran
[2] Shahid Beheshti Univ, Med Plants & Drugs Res Inst, Dept Biol, GC, Tehran 1983963113, Iran
关键词
click reaction; strecker synthesis; a-aminonitrile; Huisgen reaction; ALPHA-AMINO NITRILES; CHEMISTRY; ROUTE;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New N-substituted alpha-aminonitrile derivatives from menthol were synthesized by consecutive succinic ester formation, propargylation, 1,3-dipolar Huisgen cycloaddition and Strecker reaction. The structures of the synthesized compounds were confirmed by diverse spectroscopic techniques including H-1-NMR, C-13-NMR, ESI-MS and IR. The novel synthesized compounds were evaluated for their in vitro antibacterial activities against Staphylococcus aureus as Gram-positive and Escherichia coli as Gram-negative bacteria. These compounds demonstrated a strong inhibitory effect against S. aureus with the minimum inhibitory concentration (MIC) values ranged from 32-128 mu g mL(-1). Derivatives 6a(2), 6b(1), 6b(4) and 6b(5) with a MIC value of 32 mu g mL(-1) exhibited the best inhibitory effects.
引用
收藏
页码:577 / +
页数:18
相关论文
共 50 条
  • [41] Novel series of acridone-1,2,3-triazole derivatives: microwave-assisted synthesis, DFT study and antibacterial activities
    Aarjane, Mohammed
    Slassi, Siham
    Tazi, Bouchra
    Maouloua, Mohamed
    Amine, Amina
    JOURNAL OF CHEMICAL SCIENCES, 2019, 131 (08)
  • [42] Synthesis and Phytotoxic Activity of 1,2,3-Triazole Derivatives
    Borgati, Thiago F.
    Alves, Rosemeire B.
    Teixeira, Robson R.
    de Freitas, Rossimiriam P.
    Perdigao, Thays G.
    da Silva, Silma F.
    dos Santos, Aline Aparecida
    Bastidas, Alberto de Jesus O.
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2013, 24 (06) : 953 - U805
  • [43] Synthesis and antibacterial activity of some heterocyclic β-enamino ester derivatives with 1,2,3-triazole
    Chen, MD
    Lu, SJ
    Yuan, GP
    Yang, SY
    Du, XL
    HETEROCYCLIC COMMUNICATIONS, 2000, 6 (05) : 421 - 426
  • [44] Synthesis of Macrocycles Containing 1,2,3-Triazole Motifs
    Hradilova, Ludmila
    Grepl, Martin
    Hlavac, Jan
    Lycka, Antonin
    Hradil, Pavel
    SYNTHESIS-STUTTGART, 2012, 44 (09): : 1398 - 1404
  • [45] Synthesis and biological evaluation of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties
    Mao, Mingzhen
    Li, Yuxin
    Liu, Qiaoxia
    Xiong, Lixia
    Zhang, Xiao
    Li, Zhengming
    JOURNAL OF PESTICIDE SCIENCE, 2015, 40 (3-4) : 138 - 142
  • [46] Design, Synthesis and Fungicidal Activities of Novel 1,2,3-Triazole Functionalized Strobilurins
    Li, Yuanxiang
    Lei, Sufang
    Liu, Yilin
    CHEMISTRYSELECT, 2019, 4 (03): : 1015 - 1018
  • [47] Design, synthesis and biological evaluation of novel pleuromutilin derivatives containing piperazine and 1,2,3-triazole linker
    Zhang, Guang-Yu
    Zhang, Zhe
    Li, Kang
    Liu, Jie
    Li, Bo
    Jin, Zhen
    Liu, Ya-Hong
    Tang, You-Zhi
    BIOORGANIC CHEMISTRY, 2020, 105
  • [48] Synthesis of 1-vinyl 1,2,3-triazole derivatives
    Dabak, K
    Akar, A
    HETEROCYCLIC COMMUNICATIONS, 2002, 8 (01) : 61 - 64
  • [49] Synthesis, Characterization, and Pharmacokinetic Studies of Novel HydroquinoneBased 1,2,3-Triazole/Amide Derivatives as Anticancer and Antibacterial Agents
    Nazreen, Syed
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 60 (SUPPL1) : S50 - S58
  • [50] A simple and facile synthesis of novel 1,2,3-triazole substituted pyrimidine derivatives
    Bakkolla, Mahesh Goud
    Taduri, Ashok Kumar
    Bhoomireddy, Rama Devi
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (06) : 2489 - 2497