Synthesis 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

Abstract

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.

Benzimidazole-Triazole Hybrids as Antimicrobial and Antiviral Agents: A Systematic Review

“…Al-Majidi et al synthesized 2-mercaptobenzimidazole derivatives 95, 96, and 97 by cyclization of intermediate precursors 93, 94, and 95 under reflux with 2N NaOH (Scheme 24). The compounds generally showed moderate antimicrobial activity against all tested strains, as can be seen in Table 8 [153]. El-masry et al synthesized compounds 98 and 99 and found that they did not exhibit antimicrobial activity (Figure 16) [154].…”

Synthesis, Characterization and Antimicrobial Evaluation for New Esters Derivatives Containing Two 1, 3, 4-Oxadiazole Units

“…The disc spread method was used for the examination of bioactivity for synthesis compounds against two types of gram-positive bacteria (Staphylococcus aureus and Basillus subtilis) and two types of gram-negative bacteria (Pseudomonas aeruginosa and E. Coli), as well as against C. albino fungi [19].…”

Synthesis, Characterization and Evaluation of Some Meldrum's Acid Derivatives as Lubricant Additives

“…Meldrum's acid's carbonyl groups showed a strong stretching band between 1788 and 1666 cm -1 [23]. The 1 H NMR spectra of the compounds showed signals at 13.13-9.92 ppm for the NH proton, 9.22-7.13 ppm for the olefinic C-H proton [24]. The signals from 8.84 to 6.42 ppm belong to the aromatic protons.…”