20224-09-3

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-1-(1H-benzimidazol-2-yl)-3-(4-methoxyphenyl)prop-2-en-1-one is used as a pharmaceutical candidate for its potential anticancer properties. The benzimidazole moiety within the compound is known to exhibit biological activities that can be harnessed for developing treatments against cancer.
Additionally, due to its antimicrobial and antifungal properties, (2E)-1-(1H-benzimidazol-2-yl)-3-(4-methoxyphenyl)prop-2-en-1-one can be utilized as an antimicrobial agent for treating infections caused by bacteria and fungi. The methoxyphenyl group may further contribute to the compound's effectiveness in these applications.
Further research is required to explore additional applications and to fully understand the scope of (2E)-1-(1H-benzimidazol-2-yl)-3-(4-methoxyphenyl)prop-2-en-1-one's potential uses in the pharmaceutical industry.

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 939-70-8 2-acetylbenzimidazole 
• 16414-04-3 1-benzimidazol-2-ylethanol 
• 95-54-5 1,2-diamino-benzene 
• 4857-01-6 2-(1H-benzo[d]imidazol-2-yl)ethanol 

Downstream Products

• 132308-71-5 4-(benzimidazol-2-yl)-6-(4-methoxyphenyl)pyrimidin-2-amine 
• 132308-54-4 2-<5-(p-anisyl)-4,5-dihydropyrazol-3-yl>benzimidazole 
• 874904-65-1 6-(1H-benzimidazol-2-yl)-2-mercapto-4-(4-methoxyphenyl)pyridine-3-carbonitrile 
• 1454686-93-1 N-(4-(2-(3-(1H-benzo[d]imidazol-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethoxy)phenyl)acetamide 
• 1575824-06-4 6-(1H-benzo[d]imidazol-2-yl)-4-(4-methoxyphenyl)-2-(2-(3-nitrophenyl)-4-oxothiazolidin-3-yl)nicotinonitrile 
• 63330-62-1 4-(1H-benzo[d]imidazol-2-yl)-5,6-dihydro-6-(4-methoxyphenyl)pyrimidine-2(1H)-thione 
• 63330-67-6 4-(1H-benzo[d]imidazol-2-yl)-5,6-dihydro-6-(4-methoxyphenyl)pyrimidine-2(1H)-one 
• 1285695-40-0 2-amino-6-(1H-benzo[d]imidazol-2-yl)-4-(4-methoxyphenyl)nicotinonitrile 
• 1456802-13-3 6-(1H-benzo[d]imidazol-2-yl)-2-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-4-(4-methoxyphenyl)nicotinonitrile 
• 1456802-39-3 6-(1H-benzo[d]imidazol-2-yl)-2-(benzylideneamino)-4-(4-methoxyphenyl)nicotinonitrile 
• 63330-75-6 2-[5-(4-methoxyphenyl)-1-phenyl-4,5-dihydro-1H-3-pyrazolyl]-1H-benzimidazole 
• 1250436-97-5 C₁₈H₁₇N₅OS 
• 1250436-85-1 C₁₈H₁₆N₄O₂ 
• 874904-58-2 3-amino-6-(1H-benzimidazol-2-yl)-4-(4-methoxyphenyl)thieno[2.3-b]pyridine-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis and fungicidal activity of novel 2-(2-alkylthio-6-phenylpyrimidin-4-yl)-1H-benzimidazoles

With the aim of exploring new benzimidazole derivative with high fungicidal activity, a series of novel 2-(2-(alkylthio)-6-phenylpyrimidin-4-yl)-1H-benzimidazoles were designed and synthesized, and their in vitro fungicidal activities were evaluated. Compounds 5a, 5f, 5g, 5h, 5i and 5l exhibited excellent fungicidal activities against Botrytis cinerea, and 5c, 5f, 5h, 5i and 5l displayed notable fungicidal activities against Sclerotinia sclerotiorum. Among them, compound 5i (R1 = fluorine, R2 = benzyl) displayed the best activity towards the two tested fungi. Docking study of 5i with β-tubulin protein revealed that the NH moiety of benzimidazole ring generated a hydrogen bond with Gln-11 residue, and the fluorine atom of benzene ring formed a hydrogen bond with Tyr-208 residue, respectively; the benzene ring of Tyr-222 and the pyrimidine ring of 5i yielded a π-π interaction. The molecular electrostatic potential analysis elucidated the nitrogen atom of benzimidazole ring, fluorine atom of benzene ring and sulfur atom of thioether moiety were located in the negative potential regions, whereas some hydrogen atoms of benzene, benzimidazole and pyrimidine rings were located in the positive potential regions. This analysis demonstrated the reason why 5i can form hydrogen bonds with amino acid residues of target protein.

Synthesis, characterization, and antimicrobial activity of benzimidazole-derived chalcones containing 1,3,4-oxadiazole moiety

A series of novel benzimidazole-derived chalcones containing the 1,3,4-oxadiazole moiety were synthesized and characterized by IR, 1H, 13C NMR, and mass spectra and elemental analysis. The synthesized compounds were evaluated for their efficiency as antibacterial agents against two Gram-positive and Gram-negative strains of bacteria along with antifungal activity against three fungal species. Antibacterial activity revealed that tested compounds exhibited potent activity whereas some compounds exhibited moderate antifungal activity as compared to the standards.

Synthesis and characterization of novel benzimidazole bearing pyrazoline derivatives as potential antimicrobial agents

A new series of compounds N-(4-(2-(3-(1H-benzo[d]imidazol-2-yl)-5-(aryl)-4, 5-dihydro-1H-pyrazol-1-yl)-2-oxoethoxy)phenyl)acetamides (5a-u) were synthesized and structures of these compounds were elucidated by spectral (IR, 1H NMR, 13C NMR, and mass spectra) analysis. Antimicrobial activity was measured against Escherichia coli (MTCC 443), Pseudomonas aeruginosa (MTCC 1688), Staphylococcus aureus (MTCC 96), Streptococcus pyogenes (MTCC 442), Candida albicans (MTCC 227), Aspergillus niger (MTCC 282), and Aspergillus clavatus (MTCC 1323) by serial broth dilution method. Evaluation of antimicrobial activity revealed that compounds 5f, 5i, 5q, and 5t were the most active antibacterial, while compounds 5e, 5g, 5h, 5j, 5p, 5r, and 5u were the most potent antifungal agents as compared to standard drugs and thus could be promising new lead molecules.

Synthesis, antimicrobial and cytotoxic activity of 2-azetidinone derivatives of pyridyl benzimidazoles

In the present study, a series of novel 6-(1H-benzo[d]imidazol-2-yl)-2-(3- chloro-2-oxo-4-phenylazetidin-1-yl)-4-(aryl)nicotinonitriles 6a-o were efficiently synthesized and evaluated for their in vitro antibacterial activity against Gram-positive (Staphylococcus aureus and Streptococcus pyogenes), Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria and fungal (Candida albicans, Aspergillus niger and Aspergillus clavatus) strains. The results of antimicrobial study revealed that compounds 6b, 6c, 6d, 6h and 6i exhibited substantial antibacterial activity while compounds 6c and 6h emerged as the most potent antifungal agents compared to the standard drugs chloramphenicol and ketoconazole, respectively. From the standpoint of SAR studies, it was observed that the presence of electron-withdrawing groups remarkably enhances the antibacterial activity of newly synthesized compounds. Further, the results of preliminary MTT cytotoxicity studies on HeLa cells suggested that potent antimicrobial activity of 6b, 6c, 6d, 6h and 6i is accompanied by low level of cytotoxic concentrations. All the newly synthesized analogues were characterized by IR, 1H NMR, 13C NMR and mass spectral data. Springer Science+Business Media 2013.

Synthesis, antimicrobial, and cytotoxic activities of novel benzimidazole derivatives bearing cyanopyridine and 4-thiazolidinone motifs

A series of 6-(1H-benzo[d]imidazol-2-yl)-2-(2-(3-nitrophenyl)-4- oxothiazolidin-yl)-4-(aryl)nicotinonitriles 5a-l were synthesized and characterized by IR, 1H NMR, 13C NMR, and mass spectrometry techniques. These novel compounds 5a-l were screened for their in vitro antimicrobial activity against different bacterial and fungal strains and in vitro cytotoxicity study (HeLa cell line) using MTT colorimetric assay. The results demonstrated that compounds 5c , 5e, and 5i-k exhibited excellent antibacterial activity, while compounds 5d, 5i, and 5k were found to be the most potent antifungal agents. From the standpoint of SAR studies, it was observed that the presence of electron donating groups remarkably enhanced the antimicrobial activity of newly synthesized compounds. Further, the results of preliminary MTT cytotoxicity studies on HeLa cells suggested that potent antimicrobial activity of 5c-e and 5i-k was accompanied by low cytotoxicity. Springer Science+Business Media 2014.

Synthesis Of 1H-benzo [D] imidazolo-2-Yl-3-Aryl-4- chlorocyclobutanone-2-Yl-Methanones, 1H-benzo [D] imidazolo-2-Yldihydro- 5-arylthiophen-3(2H)-One-2-yl-methanones, 4-(1H-benzo [D] imidazol-2-Yl)- 5,6-dihydro-6-arylpyrimidine-2(1H)-thiones and 4-(1H)- benzo [D] imidazol-2-Yl)-5,6-dihydro-6-arylpyrimidine-2-(1H)-ones

1-(1H-Benzo [d] imidazol-2-yl) ethanol (1) on treatment with acetic acid gave 1- (1H-benzo [d] imidazol-2-yl) ethanone (2). Compound 2 when treated with different aldehydes yielded arylidine derivatives (3a-e). Compound 3 on cyclization with chloroacetyl chloride, thioglycolic acid, thiourea and urea yielded azitidinones (4a-e) 4-thiazolidinones (5a-e), pyrimidinethiones (6a-d) and pyramidinones (7a-d) respectively. The structures of the products were established by spectral analysis like IR, 1H NMR and Mass spectroscopy.

Microwave assisted transformation of benzimidazolyl chalcones into N 1-substituted pyrazolines and evaluation of their antimicrobial activities

1-Benzimidazolyl-3-aryl-prop-2-ene-1-ones 2 have been transformed into N1-substituted pyrazoline derivatives by the interaction with phenyl hydrazine, thiosemicarbazide and hydrazine hydrate in the presence of formic acid under solvent microwave induced protocol. The structure of newly synthesized compounds have been confirmed on the basis of their elemental analysis and spectral data. Newly synthesized compounds have been evaluated for their antimicrobial activity in against E. coli, K. pneumonae, P. aeruginosa and B. subtilis using paper disc method. Some of the compounds have shown significant activity against the pathogens.

Synthesis and biological evaluation of some novel-3-(5-substituted benzimidazol-2-yl)-5-arylisoxazolines

The synthesis of a new series of 3-(5-substituted benzimidazol-2-yl)-5-arylisoxazolines (6a-h) was achieved in excellent yields by the condensation of 1-(1H-benzimidazol-2-yl)-3-(substituted phenyl)prop-2-en-1-ones (5a-h) with hydroxylamine at room temperature. These 1-(1H-benzimidazol-2-yl)-3-(substituted phenyl)prop-2-en-1-ones (5a-h) were obtained by the condensation of 2-acetyl benzimidazoles (4a-d) with different aromatic aldehydes, which in turn were obtained by the oxidation of 2-(α-hydroxy)ethyl benzimidazoles (3a-d) prepared by the reaction of o-phenylenediamines (1a-d) with α-hydroxy propionic acid 2. The synthesized compounds were characterized by their IR, 1H NMR and MS analyses. These compounds were screened for their antibacterial and antifungal activity by standard methods and found some of them active.

Solid phase synthesis of benzimidazole ketones and benzimidazole chalcones under solvent-free conditions

Oxidation of 1-alkyl/aralkyl-2-(α-hydroxyalkyl/aryl)benzimidazoles 1 with KMnO4 on neutral alumina under solid phase conditions gives the corresponding ketones, 1-alkyl/aralkyl-2-acyl-benzimidazoles 2. Compound 2a (R2 = CH3) on condensation with aromatic aldehydes in the presence of solid NaOH under solvent-free conditions, yields the corresponding chalcones, 1-alkyl/aralkyl-2-benzimidazole aryl vinyl ketone 3.

Synthesis and antimicrobial activity of 2-imino-4-(benzimidazol-2′ -yl)-6-aryl-6H-2,3-dihydro-1,3-thia/oxazines

2-Acetylbenzimidazole (1) on condensation with various aldehydes yields the chalcones (2a-1) which on cyclization with thiourea/urea in alc. KOH furnish the corresponding 2-imino-4-(benzimidazol-2′ -yl)-6-aryl-6H-2,3-dihydro-1,3-thiazines/1,3-oxazines (3a-1, 4a-1). The compounds have been evaluated for their antibacterial and antifungal activities.