126359-46-4Relevant academic research and scientific papers
Synthesis, molecular docking, and biological evaluation of nitroimidazole derivatives as potent urease inhibitors
Talebi, Meysam,Hamidian, Elham,Niasari-Naslaji, Fatemeh,Rahmani, Sogand,Hosseini, Faezeh Sadat,Boumi, Shahin,Montazer, Mohammad Nazari,Asadi, Mehdi,Amanlou, Massoud
, p. 1220 - 1229 (2021)
The objective of this study was to design new nitroimidazole-based derivatives as strong urease inhibitors for the treatment of H. pylori infections. New series of nitroimidazole derivatives, 4a–k, were synthesized by using TBTU as the catalyst and assaye
Design, synthesis, and antibacterial evaluation of new Schiff's base derivatives bearing nitroimidazole and pyrazole nuclei as potent E. coli FabH inhibitors
Sangani, Chetan B.,Makwana, Jigar A.,Duan, Yong-Tao,Tarpada, Umesh P.,Patel, Yogesh S.,Patel, Ketan B.,Dave, Vivek N.,Zhu, Hai-Liang
, p. 10137 - 10149 (2016/01/12)
New Schiff's base derivatives 5a-j have been synthesized by reaction between 5-aryloxypyrazole-4-carbaldehydes 3a-j and 2-(2-methyl-5-nitro-1Himidazol- 1-yl)acetohydrazide 4 in the presence of nickel (II) nitrate as a catalyst in ethanol at room temperatu
Schiff's base derivatives bearing nitroimidazole and quinoline nuclei: New class of anticancer agents and potential EGFR tyrosine kinase inhibitors
Makawana, Jigar A.,Sangani, Chetan B.,Lin, Lin,Zhu, Hai-Liang
, p. 1734 - 1736 (2014/04/17)
New Schiff's base derivatives 5a-j have been synthesized by reaction between 2-phenoxyquinoline-3-carbaldehydes 3a-j and 2-(2-methyl-5-nitro-1H- imidazol-1-yl)acetohydrazide 4 in presence of nickel(II) nitrate as a catalyst in ethanol under reflux in good
Nitroimidazolyl hydrazones are better amoebicides than their cyclized 1,3,4-oxadiazoline analogues: In vitro studies and Lipophilic efficiency analysis
Wani, Mohmmad Younus,Bhat, Abdul R.,Azam, Amir,Athar, Fareeda
, p. 190 - 199 (2013/07/27)
Two series of compounds with hydrazone derivatives (HZ1-HZl2, series 1) and oxadiazoline derivatives (OZ1-OZ12, series 2) of the 2-methyl-5-nitro-1H- imidazole scaffold were designed and synthesized. Physicochemical properties and Lipophilic efficiency (LipE) analysis predicted higher intrinsic quality of the acylhydrazone derivatives (series 1) than their corresponding oxadiazoline analogues (series 2). In vitro antiamoebic results supported the above findings and validated that the acylhydrazone derivatives (HZ1-HZl2) show better activity than the oxadiazoline derivatives (OZ1-OZ12). MTT assay, using HepG2 cell line, revealed noncytotoxic nature of the compounds. The most promising results were observed for compounds HZ5 (IC50 = 0.96 μM) and HZ9 (IC 50 = 0.81 μM) both in silico and in vitro. Analysis of the Lipophilic efficiency (LipE) of the compounds provided new insight for the design of potent and selective amoebicides.
Design, synthesis and antimicrobial activities evaluation of Schiff base derived from secnidazole derivatives as potential FabH inhibitors
Li, Yao,Zhao, Chang-Po,Ma, Hua-Ping,Zhao, Meng-Yue,Xue, Ya-Rong,Wang, Xiao-Ming,Zhu, Hai-Liang
, p. 3120 - 3126 (2013/07/05)
FabH, β-ketoacyl-acyl carrier protein (ACP) synthase III, is critically important to the initiation of fatty acid biosynthesis and is highly conserved among Gram-positive and Gram-negative bacteria. A series of novel secnidazole derivatives (1-20) were sy
Design, synthesis and antimicrobial activities of nitroimidazole derivatives containing 1,3,4-oxadiazole scaffold as FabH inhibitors
Li, Yao,Luo, Yin,Hu, Yang,Zhu, Di-Di,Zhang, Shuai,Liu, Zhi-Jun,Gong, Hai-Bin,Zhu, Hai-Liang
experimental part, p. 4316 - 4322 (2012/08/28)
Nitroimidazoles and their derivatives have drawn continuing interest over the years because of their varied biological activities, recently found application in drug development for antimicrobial chemotherapeutics and antiangiogenic hypoxic cell radiosensitizers. In order to search for novel antibacterial agents, we designed and synthesized a series of secnidazole analogs based on oxadiazole scaffold (4-21). Among these compounds, 4 and 7-21 were reported for the first time. These compounds were tested for antibacterial activities against Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis and Staphylococcus aureus. This new nitroimidazole derivatives class demonstrated strong antibacterial activities. Escherichia coli β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitory assay and docking simulation indicated that the compounds 2-(2-methoxyphenyl)-5-((2- methyl-5-nitro-1H-imidazol-1-yl)methyl)-1,3,4-oxadiazole (11) with MIC of 1.56-3.13 μg/mL against the tested bacterial strains and 2-((2-methyl-5- nitro-1H-imidazol-1-yl)methyl)-5-(2-methylbenzyl)-1,3,4-oxadiazole (12) with MIC of 1.56-6.25 μg/mL were most potent inhibitors of Escherichia coli FabH.
Synthesis and characterization of a new bidentate ligand 5-substituted-(2-methyl-5-nitro-1-imidazomethyl)-1,3,4-oxadiazole-2-thione and its metal complexes of ag(i), cu(ii) and zn(ii)
Kazi, Shabbir A.
scheme or table, p. S127-S136 (2012/06/15)
A new ligand (2-methyl-5-nitro-1-imidazomethyl)-1,3,4-oxadiazole- 2-thione (L) and its Ag(I),Cu(II) and Zn(II) complexes were synthesized. The authenticity of the ligand and its transition metal complexes were established by elemental analyses, conductance and magnetic susceptibility measurements, as well as spectroscopic (IR, 1H NMR, electronic, mass and ESR) and thermal studies. The IR spectral studies revealed the existence thiol-thione tautamerism in the ligand molecule. The magnetic and electronic spectral studies suggest an octahedral geometry for Cu(II) and Zn(II) complexes. The ligand acts as a bidentate coordinating through the N-3 nitrogen and the exocyclic sulfur atoms of oxadiazole rings. Antimicrobial screening of the ligand and its metal complexes were determined against the bacteria Escherichia coli and Salmonella paratyphi A.
Convenient syntheses of 5-[(2-Methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3, 4-oxadiazole-2(3H)thione and N-substituted 2-amino-5-[(2-methyl-5-nitro-1H- imidazol-1-yl)methyl]-1,3,4-thiadiazoles
Mirzaei, Javad,Amini, Mohsen,Pirelahi, Hooshang,Shafiee, Abbas
, p. 921 - 925 (2008/09/21)
(Chemical Equation Presented) Oxidation of metronidazole (4) with sodium dichromate yielded the corresponding 2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetic acid (5) which was esterified with 1-butanol to give butyl 2-(2-methyl-5-nitro- 1H-imidazol-1-yl)acetate (8). Reaction of the latter with hydrazine hydrate gave 2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide (9). Compound 5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione (10) could be obtained through the reaction of compound 9 with carbon disulfide in basic medium. Subsequent alkylation of compound 10 afforded alkyl 2-(5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3,4-oxadiazol-2-ylthio) acetate (11) in good yield. Reaction of hydrazide 9 with substituted isothiocynate yielded 1-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetyl]-4-aryl(or ethyl)thiosemicarbazide (12) which was cyclized in acidic media to N-substituted 2-amino-5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3,4-thiadiazole (13).
Synthesis of 1,3,4-oxadiazoles carrying imidazole moiety
Frank, Priya V.,Kalluraya, Balakrishna
, p. 1456 - 1459 (2007/10/03)
A new series of 1,3,4-oxadiazoline derivatives 5a-1 have been obtained by cyclisation of various hyerazones 4 with acetic anhydride. The hydrazones 4 in turn are obtained by the reaction of appropriate carbonyl compound with 2-methyl-5-nitroimidazole-1-acethydrazide 3. The new products are characterized by spectral and analytical data. Most of the tested compounds show promising antibacterial and antifungal activity.
