84587-80-4

Upstream product

• 934-32-7 1H-benzimidazol-2-amine 
• 95-54-5 1,2-diamino-benzene 
• 344413-06-5 1-chloroacetyl-1H-benzoimidazol-2-ylamine 
• 79-04-9 chloroacetyl chloride 

Relevant academic research and scientific papers

Synthesis and antifungal activity of novel 2-benzimidazolylimino-5- arylidene-4-thiazolidinones

(Chemical Equation Presented) A series of 5-arylidene derivatives 3a-k, as potential antifungal agents, were synthesized in good to high yields by the reaction of 2-benzimidazolylimino-4-thiazolidinone and corresponding aromatic aldehyde in a buffered med

Design and synthesis of benzimidazole-based Rho kinase inhibitors for the treatment of glaucoma

Rho kinase inhibitors (ROCK II) play a key role in glaucoma management attributed to their IOP lowering ability and neuroprotective effects. In the present study, a series of novel benzimidazole derivatives (9a–m) has been synthesized and evaluated for their IOP lowering, Rho kinase inhibitory and antioxidant properties. The synthesized compounds were found to be lipophilic and showed a significant IOP lowering effect both in the treated and the contralateral eye comparable to the reference standard fasudil. The nitrophenyl piperazine substituted compound 9j exhibited significant IOP lowering (51.56%) and an inhibition of 57.25 and 77.92% towards ROCK II enzyme at a concentration of 0.5 and 1 mM respectively. It possessed a considerable free radical scavenging activity exhibiting an IC50 value of 95.49 μg/mL in DPPH assay. The molecular docking studies of compound 9j indicated the binding of the compound at the active site of recombinant human ROCK II which makes it a promising antiglaucoma agent.

Design, synthesis and biological evaluation of 1,2,3-triazole based 2-aminobenzimidazoles as novel inhibitors of LasR dependent quorum sensing in: Pseudomonas aeruginosa

Bacteria regulate their phenotype, growth and population via a signalling pathway known as quorum sensing. In this process, bacteria produce signalling molecules (autoinducers) to recognize their population density. Inhibiting this quorum sensing signalling pathway is one of the potential methods to treat bacterial infection. 2-Aminobenimdazoles are reported to be the strongest inhibitors of quorum sensing against wild-type P. aeruginosa. 1,2,3-Triazole based acyl homoserine lactones are found to be good inhibitors of the quorum sensing LasR receptor. Hence, in our current study, forty 1,2,3-triazole based 2-aminobenzimdazoles were synthesized and characterized using IR, NMR, MS and elemental analysis. A single crystal was developed for N-(1H-benzo[d]imidazol-2-yl)-2-(4-nonyl-1H-1,2,3-triazol-1-yl)acetamide (6d). All final compounds were screened for in vitro quorum sensing inhibitory activity against Pseudomonas aeruginosa. The quorum sensing inhibitory activity was determined in the LasR expressing P. aeruginosa MH602 reporter strain by measuring green fluorescent protein production. Among the title compounds, N-(1H-benzo[d]imidazol-2-yl)-2-(4-(4-chlorophenyl)-1H-1,2,3-triazol-1-yl)acetamide (6i) exhibited good quorum sensing inhibitory activity of 64.99% at 250 μM. N-(1H-Benzo[d]imidazol-2-yl)-2-(4-(4-nitrophenyl)-1H-1,2,3-triazol-1-yl)acetamide (6p) exhibited the most promising quorum sensing inhibitory activity with 68.23, 67.10 and 63.67% inhibition at 250, 125 and 62.5 μM, respectively. N-(1H-Benzo[d]imidazol-2-yl)-2-(4-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-1-yl)acetamide (6o) and N-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)-2-(4-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-1-yl)acetamide (7l) also exhibited 64.25% and 65.80% quorum sensing inhibition at 250 μM. Compound 6p, the most active quorum sensing inhibitor, also displayed low cytotoxicity at the tested concentrations (25, 50 and 100 μM) against normal human embryonic kidney cell lines. Finally, a docking study using Schrodinger Glide elucidated the possible putative binding mode of the significantly active compound 6p at the active site of the target LasR receptor (PDB ID: 2UV0).

Identification of thienopyridine carboxamides as selective binders of HIV-1: Trans Activation Response (TAR) and Rev Response Element (RRE) RNAs

Small organic molecules that can selectively bind to RNA with specificity are relatively rare. Here we report the synthesis, biochemical and structural studies of thienopyridine carboxamide derivatives with the capacity of selectively recognizing and binding with HIV-1 TAR and RRE RNAs that are essential elements for viral replication.

Synthesis and antimicrobial activity of some new N-(1h-benzimidazol-2-yl)-2-mercaptoacetamide derivatives

Background: Due to multi-drug, extended-drug, and pandrug resistance phenotypes, bacterial resistance to antibiotics and fungal infections are a general health issue. Particulary, increase of fungal infections due to secondary cause of human diseases have been observed. An extensive variety of benzimidazole derivatives have been characterized for their chemotherapeutic significance. Benzimidazole derivatives have received important attention because of pharmacological significance during current years, especially antimicrobial, anti-fungal, antitubercular, antioxidant, anti-Alzheimer’s disease and antihypertension activities. Methods: Some N-(1H-benzimidazol-2-yl)-2-mercaptoacetamide derivatives (2a-h) were synthesised and evaluated for their antimicrobial activity. The title compounds were gained by reacting N-(1H-benzimidazol-2-yl)-2-chloroacetamide with some substituted 2-mercapto heterocyclic rings. The synthesised compounds were investigated for their antimicrobial activities against C. albicans (ATCC 24433), C. krusei (ATCC 6258), C. glabrata (ATCC90030), C. parapsilosis (ATCC 22019), E. coli (ATCC 25922), E. coli (ATCC 35218), E. feacalis (ATCC 51299), E. feacalis (ATCC 29212), S. aureus (ATCC 25923), K. pneumoniae (ATCC 700603), P. aeruginosa (ATCC 27853). Results: The compounds showed high antifungal activity when compared with standard drug ketoconazole. In addition, all compounds (MIC 100 μg/mL) showed inhibitor activity against P. aeruginosa at two fold concentration of chloramphenicol (MIC 50 μg/mL). Also, compounds 2a, 2c and 2e (MIC: 50 μg/mL) have equal effect against E. coli (ATCC 35218) and more effective than other compounds (MIC of chloramphenicol: 100 μg/mL). Conclus?on: All compounds showed notable activity. Compounds have determined to possess higher antifungal activity than antibacterial activity. Additionally, compounds 2a with 1-methyltetrazole, 2c with benzothiazole and 2e with 6-chlorobenzothiazole moieties were found as the most active compounds.

Azolylthioacetamides as a potent scaffold for the development of metallo-β-lactamase inhibitors

In an effort to develop new inhibitors of metallo-β-lactamases (MβLs), twenty-eight azolylthioacetamides were synthesized and assayed against MβLs. The obtained benzimidazolyl and benzioxazolyl substituted 1–19 specifically inhibited the enzyme ImiS, and 10 was found to be the most potent inhibitor of ImiS with an IC50 value of 15 nM. The nitrobenzimidazolyl substituted 20–28 specifically inhibited NDM-1, with 27 being the most potent inhibitor with an IC50 value of 170 nM. Further studies with 10, 11, and 27 revealed a mixed inhibition mode with competitive and uncompetitive inhibition constants in a similar range as the IC50 values. These inhibitors resulted in a 2–4-fold decrease in imipenem MIC values using E. coli cells producing ImiS or NDM-1. While the source of uncompetitive (possibly allosteric) inhibition remains unclear, docking studies indicate that 10 and 11 may interact orthosterically with Zn2 in the active site of CphA, while 27 could bridge the two Zn(II) ions in the active site of NDM-1 via its nitro group.

Azolylthioacetamide: A highly promising scaffold for the development of metallo-β-lactamase inhibitors

A new scaffold, azolylthioacetamide, was constructed and assayed against metallo-β-lactamases (MβLs). The obtained molecules specifically inhibited MβL ImiS, and 1c was found to be the most potent inhibitor, with a Ki = 1.2 μM using imipenem as substrate. Structure-activity relationships reveal that the aromatic carboxyl improves inhibitory activity of the inhibitors, but the aliphatic carboxyl does not. Compounds 1c-d and 1h-i showed the best antibacterial activities against E. coli BL21(DE3) cells producing CcrA or ImiS, resulting in 32- and 8-fold reduction in MIC values, respectively; 1c and 1f-j resulted in a reduction in MIC against P. aeruginosa. Docking studies revealed that 1a, 1c, and 1d fit tightly into the substrate binding site of CphA as a proxy for ImiS with the aromatic carboxylate forming interactions with Lys224, the Zn(II) ion, the backbone of Asn233, and hydrophobic portions of the inhibitors aligning with hydrophobic patches of the protein surface.

Synthesis and QSAR modeling of novel benzimidazolo thiazolidinones, thiazinones and 5-arylidene-2-imino thiazolidinones as antibacterial agents

A novel series of benzimidazolo thiazolidinones, thiazinones and 5-arylidene-2-imino thiazolidinones were synthesized and evaluated for antibacterial activity. The compounds were synthesized in excellent yield and the structures were characterized on the basis of IR, 1H-NMR and MASS spectral data. Most of the synthesized compounds showed good antibacterial activity against Gram-positive and Gram-negative bacteria. QSAR study was carried out with synthesized compounds using molecular descriptors such as electronic, thermodynamic and steric. Molecular descriptors were used to derive QSAR models between antibacterial activity and structural properties. QSAR study suggested the need of a bulky group to enhance the antibacterial activity in these series of compounds.

Synthesis of some new benzimidazolyl thioxoacetamide derivatives

Treatment of 2-aminobenzimidazole 1 with chloroacetyl chloride 2 in dry benzene gave N-(H-1,3-benzimidazol-2-yl)-2-chloroacetamide 3. Further reaction of 3 with a mixture of elemental sulfiir and corresponding amine in dimethylformamide (DMF) under room t