5-Amino-2-mercaptobenzimidazole

Synthesis and Pharmacological Evaluation of Novel Pleuromutilin Derivatives with Substituted Benzimidazole Moieties.[Pubmed:27834819]

Molecules. 2016 Nov 8;21(11). pii: molecules21111488.

A series of novel pleuromutilin derivatives with substituted benzimidazole moieties were designed and synthesized from pleuromutilin and 5-Amino-2-mercaptobenzimidazole through sequential reactions. All the newly synthesized compounds were characterized by IR, NMR, and HRMS. Each of the derivatives was evaluated in vitro for their antibacterial activity against Escherichia coli (E. coli) and five Gram (+) inoculums. 14-O-((5-amino-benzimidazole-2-yl) thioacetyl) mutilin (3) was the most active compound and showed highest antibacterial activities. Furthermore, we evaluated the inhibition activities of compound 3 on short-term S. aureus and MRSA growth and cytochrome P450 (CYP). The bioassay results indicate that compound 3 could be considered potential antibacterial agents but with intermediate inhibition of CYP3A4.

Experimental and density functional theory study of Raman and SERS spectra of 5-amino-2-mercaptobenzimidazole.[Pubmed:26335062]

Spectrochim Acta A Mol Biomol Spectrosc. 2016 Jan 15;153:344-8.

Raman spectroscopy, surface-enhanced Raman spectroscopy (SERS) and density functional theory (DFT) simulations were employed to study 5-Amino-2-mercaptobenzimidazole (5-A-2MBI) molecules. Ag colloids were used as SERS substrates which were prepared by using hydroxylamine hydrochloride as reducing agent. Raman vibration modes and SERS characteristic peaks of 5-A-2MBI were assigned with the aid of DFT calculations. The molecular electrostatic potential (MEP) of 5-A-2MBI was used to discuss the possible adsorption behavior of 5-A-2MBI on Ag colloids. The spectral analysis showed that 5-A-2MBI molecules were slightly titled via the sulfur atoms adhering to the surfaces of Ag substrates. The obtained SERS spectral intensity decreased when lowering the 5-A-2MBI concentrations. A final detection limit on the concentration of 5x10(-7) mol . L(-1) was gained. SERS proved to be a simple, fast and reliable method for the detection and characterization of 5-A-2MBI molecules.

Design, synthesis, fabrication and in vitro evalution of mucoadhesive 5-amino-2-mercaptobenzimidazole chitosan as low water soluble drug carriers.[Pubmed:25229809]

Eur J Pharm Biopharm. 2014 Nov;88(3):986-97.

Mucoadhesive thiolated chitosan suitable as a carrier for low water soluble drugs was designed and synthesized by conjugating 5-Amino-2-mercaptobenzimidazole (MBI) using methylacrylate (MA) as the linking agent. A 14.4% degree of substitution of MA, as determined by (1)H NMR analysis, and 11.86+/-0.01mumol thiol groups/g of polymer, as determined by Ellman's method, was obtained. The MBI-MA-chitosan had an 11-fold stronger mucoadhesive property compared to unmodified chitosan at pH 1.2, as determined by the periodic acid: Schiff colorimetric method. Chitosan, MA-chitosan and MBI-MA-chitosan were fabricated as well-formed microspheres using electrospray ionization, including an entrapment efficiency of simvastatin (SV) of over 80% for the MBI-MA-chitosan. The mucoadhesiveness of the SV-loaded MBI-MA-CS microspheres was still higher than that for SV-loaded chitosan at pH 1.2 and 6.4. The SV-loaded MBI-MA-CS microspheres revealed a reduced burst effect and an increased release rate (more than fivefold higher than pure SV) of SV over 12h.