Open AccessSynthesis and Identification of Some New Derivatives of ([Benzyl Thio) Benzimidazole -N- (Methylene-5-Yl)] - 4,5- Di Substituted 1,2,4-Triazole and Evaluation of Their Activity as Antimicrobial and Anti-Inflammatory Agents
Author(s) -
M. H. Al-Majidi Suaad,
A.R. Ibrahim Halah,
A.H. AL-issa Yasser
Publication year - 2021
Publication title -
iraqi journal of science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.152
H-Index - 4
eISSN - 2312-1637
pISSN - 0067-2904
DOI - 10.24996/ijs.2021.62.4.2
Subject(s) - chemistry , thio , 1,2,4 triazole , hydrazine (antidepressant) , semicarbazide , benzimidazole , hydrate , yield (engineering) , carbon 13 nmr , methylene , proton nmr , organic chemistry , solvent , nuclear chemistry , medicinal chemistry , chromatography , materials science , metallurgy
New 2-Mercaptobenzimidazole derivatives were synthesized. 4,5-disubsitituted 1,2,4-Triazole compounds 1b-2c were synthesized from 2-(benzylthio) benzimidazole compound a, which was then reacted with (NaH) in dioxane at a temperature of (0-5 C°) to produce the salt of compound a. Then the salt was reacted with ethyl chloro acetate to yield Ethyl 2-(benzylthio) benzimidazole acetate compound b. Compound b was converted to triazole derivatives by two pathways. The first pathway was reacting compound b with semicarbazide, thiosemicarbazide and phenylsemicarbazide in DMSO as a solvent to gain compounds 1b-3b, which were then cyclized by refluxed with 2N (NaOH) to yield 1,2,4-triazole derivatives compounds 4b-6b. The second pathway involved the treatment of compound b with hydrazine hydrate to produce N-acetohydrazide-2-(benzyl thio) benzimidazole c. Compound c was refluxed with carbon disulfide (CS2) in KOH alcoholic solution to obtain the salt compound 1c. The salt was treated with hydrazine hydrate to yield 1,2,4-triazole derivative compound 2c. The newly synthesized compounds b-2c were identified by FTIR, 1H-NMR and 13C-NMR and their physical properties were measured. Furthermore, their anti-microbial activities were tested against two Gram-positive and two Gram-negative bacteria and against one strain of fungi. Also, some of these synthesized compounds were tested for their anti-inflammatory activities.