Synthesis and Antimicrobial Activity of Glycosylated 2-Aryl‑5‑amidinobenzimidazoles

Abstract

A series of new glycosylated 2-aryl-5-amidinobenzimidazoles derived from four different carbohydrates (D-glucose, D-galactose, N-acetyl-D-glucosamine and lactose) were synthesized by the condensation of the appropriate 4-formyl-3-methoxyphenyl glycoside with 4-amidino-or 4-N-isopropylamidino-ortho-phenylenediamine hydrochloride. All the compounds were properly characterized by high resolution mass spectrometry, uni-and bidimensional 1 H and 13 C nuclear magnetic resonance and then were evaluated for their antibacterial and antifungal potential. Considering the antifungal potential of them, two derivatives were active against Candida parapsilosis at 96.4 µmol L -1 and another was active against this same strain at 83.5 µmol L -1 . In addition, one benzamidine showed activity against Candida glabrata at 97 µmol L -1. Considering the antibacterial potential of these compounds, six of them showed better activity against three different stains: three of them with IC 50 of 96.4, 97 and 83.5 µmol L -1 against Gram-positive Micrococcus luteus, the other two with IC 50 96.5 and 96.4 µmol L -1 against Gram-positive Enterococcus faecalis and one against Gram-negative Escherichia coli at 90.5 µmol L -1 . These findings suggest this structural pattern can be employed for design of more potent agents for discovery of new antimicrobial drug candidates.

Synthesis, Characterization and Response of Newer Benzamidine Analogues against Porphyromonas gingivalis mediated Peri-Implantitis

“…The antimicrobial and cell viability research on novel benzamidine analogues (NBA) indicated that presence of NO 2 and Cl (electron withdrawing groups) in compounds 3a and 3b, respectively on 4 th position of benzyl ring offers significant MIC, MBC and safety. Findings of current investigation were also found to agree with the findings of other investigations on inhibitory response of benzamidines towards P. gingivalis [1][2][3]23,24]. Therefore, the current cell viability and antimicrobial research findings supports significant safety and efficacy of NBA.…”

“…The progress of reaction was monitored by thin layer chromatography (TLC) and melting point measurements using Spectroline UV CM-26 and Stuart Analogue Melting Point SMP11, respectively. The chemical structures of the synthesized compounds were confirmed based on attenuated total reflectance-infrared (ATR-IR) spectral, 1 H & 13 C nuclear magnetic resonance (NMR) spectral and direct infusion mass spectrometry (DIMS) spectral data.…”

“…Among the synthetic compounds, the high antimicrobial potential of benzamidines always withdraws the investigators' attention [1]. Recently the synthesis of benzamidine analogues has become a major subject of interest for many researchers attributed to their antimicrobial properties [2].…”

Design, Synthesis, and Antifungal Activities of Hymexazol Glycosides Based on a Biomimetic Strategy

“…The crude product was dried with anhydrous magnesium sulfate and filtered; then dichloromethane was removed by depressurization. The crude product was further purified by column chromatography (SiO 2 , DCM/MeOH = 100/1) …”

“…The crude product was further purified by column chromatography (SiO 2 , DCM/MeOH = 100/1). 32 Data for 3-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-5-methylisoxazole (3) Synthesis of Hymexazol Glycosides (4,5,14,15). The compounds (2,3,12,13) (2 equiv) were dissolved in 10 mL of methanol, and sodium methoxide (1 equiv) was add.…”