Synthesis and biological activity of novel benzimidazole derivatives as potential antifungal agents

Abstract

In the present study, a series of novel benzimidazole derivatives containing chrysanthemum acid moieties was designed and synthesized. Preliminary investigation of biological activity indicated that all of the compounds exhibited lower activity than that of beta-cypermethrin against Plutella xylostella and Lipaphis erysimi; meanwhile, they showed good inhibitory activity against Botrytis cinerea and Sclerotinia sclerotiorum in vitro. The fungicidal activity of compound 8a against B. cinerea was approximately equal to that of thiabendazole and was twice as active against S. sclerotiorum as was thiabendazole. In addition, compound 9e displayed the most potent inhibitory activity against both fungi and was almost twice as potent as thiabendazole.

2-(3,4-Dimethoxyphenyl)-N-(4-methoxyphenyl)-1-propyl-1H-benzo[d]imidazole-5-carboxamide

“…Furthermore, its spectrum showed the presence of three distinct singlet at δ 3.726, 3.838, and 3.865 ppm for their three methoxy protons attached to two phenyl rings. In 13 The structure of the compound 3 was confirmed by IR, 1 H-NMR, 13 C-NMR, and LC-MS spectral data. The 1 H-NMR spectrum of compound 3 showed a presence of a down-field singlet at δ 10.263 for its -NH proton, indicating the presence of a carboxamide group.…”

“…The synthetic procedure was optimized based on the trial experiments and the yields were not Supplementary Materials: The following are available online, Figure S1: 1 H-NMR of the compound 3, Figure S2: 13 C-NMR of the compound 3, Figure S3: LC-MS spectra of the compound 3, Figure S4: IR spectrum of the compound 3.…”

“…Optimization of substituents around the benzimidazole nucleus has resulted in many drugs like Albendazole, Mebendazole, Triclabendazole, Fenbendazole, Oxfendazole, Thiabendazole, Omeprazole, Lansoprazole, and Pantoprazole [6]. Benzimidazole and its derivatives have associated with diverse biological activities such as anti-microbial [7][8][9], anti-inflammatory and analgesic [10], anti-tubercular [11], anti-oxidant [12], anti-fungal [13], anti-convulsant/anti-diabetic [14], and anti-viral [15]. Substituted benzimidazole derivatives have found commercial applications in diverse human therapeutics, especially for treating various types of cancers [16][17][18][19][20].…”

“…'One-pot' reductive cyclization was found to be highly efficient using sodium dithionite as reductive cyclizing agent compared to other reagents [32][33][34][35]. Thus, in this paper we describe the efficient synthesis and characterization (by IR, 1 H-NMR, 13 C-NMR, and LC-MS spectral data) of new benzimidazole coupled carboxamide. derivatives have found commercial applications in diverse human therapeutics, especially for treating various types of cancers [16][17][18][19][20].…”

“…Thus, in this paper we describe the efficient synthesis and characterization (by IR, 1 H-NMR, 13 C-NMR, and LC-MS spectral data) of new benzimidazole coupled carboxamide. The structure of the compound 3 was confirmed by IR, 1 H-NMR, 13 C-NMR, and LC-MS spectral data. The 1 H-NMR spectrum of compound 3 showed a presence of a down-field singlet at δ 10.263 for its -NH proton, indicating the presence of a carboxamide group.…”