20224-10-6

Basic information

• Product Name: 2-Cinnamoylbenzimidazole
• Synonyms: 2-Cinnamoylbenzimidazole
• CAS NO: 20224-10-6
• Molecular Formula: C₁₆H₁₂N₂O
• Molecular Weight: 248.27928
• Mol File: 20224-10-6.mol

Chemical Properties

• Melting Point: 201-205 °C
• Boiling Point: 487.4°C at 760 mmHg
• Flash Point: 245.8°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 1.19E-09mmHg at 25°C
• Refractive Index: 1.723
• PKA: 10.30±0.10(Predicted)
• CAS DataBase Reference: 2-Cinnamoylbenzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cinnamoylbenzimidazole(20224-10-6)
• EPA Substance Registry System: 2-Cinnamoylbenzimidazole(20224-10-6)

Safety Data

• Hazardous Substances Data: 20224-10-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H12N2O/c19-15(11-10-12-6-2-1-3-7-12)16-17-13-8-4-5-9-14(13)18-16/h1-11H,(H,17,18)/b11-10+

Upstream product

• 100-52-7 benzaldehyde 
• 939-70-8 2-acetylbenzimidazole 
• 16414-04-3 1-benzimidazol-2-ylethanol 
• 95-54-5 1,2-diamino-benzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 4857-01-6 2-(1H-benzo[d]imidazol-2-yl)ethanol 

Downstream Products

• 146887-09-4 2,6-bis(1H-benzimidazol-2-yl)-4-phenylpyridine 
• 132308-69-1 4-(benzimidazol-2-yl)-6-phenylpyrimidin-2-amine 
• 132308-52-2 2-(5-phenyl-4,5-dihydro-1H-3-pyrazolyl)-1H-benzimidazole 
• 1164474-59-2 (E)-1-[1-(2-Oxo-2-p-tolyl-ethyl)-1H-benzoimidazol-2-yl]-3-phenyl-propenone 
• 1250436-83-9 C₁₇H₁₄N₄O 
• 1250436-95-3 C₁₇H₁₅N₅S 
• 58035-20-4 2-(1,5-diphenyl-4,5-dihydro-1H-3-pyrazolyl)-1H-benzimidazole 
• 63330-81-4 2-(5-phenyl-4,5-dihydroisoxazol-3-yl)benzimidazole 
• 1454686-79-3 N-(4-(2-(3-(1H-benzo[d]imidazol-2-yl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethoxy)phenyl)acetamide 
• 1456802-26-8 6-(1H-benzo[d]imidazol-2-yl)-2-(benzylideneamino)-4-phenylnicotinonitrile 
• 1456802-00-8 6-(1H-benzo[d]imidazol-2-yl)-2-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-4-phenylnicotinonitrile 
• 1285695-39-7 2-amino-6-(1H-benzo[d]imidazol-2-yl)-4-phenylnicotinonitrile 
• 1575823-96-9 6-(1H-benzo[d]imidazol-2-yl)-2-(2-(3-nitrophenyl)-4-oxothiazolidin-3-yl)-4-phenylnicotinonitrile 

Relevant articles and documents

Design and structure-activity relationships anticandidosic of diazaheteroaryl functionalized by Micha?l acceptors

Benzimidazole and imidazopyridine heterocycles associated with Micha?l acceptors have shown strong anticandidosic potential in our previous work. After a decade of research, we have designed, synthesized and evaluated the anticandidosic activities of seve

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.

Applications of benzimidazole derivatives in prevention and treatment of agricultural plant diseases

The invention relates to the field of medicinal chemistry, and discloses applications of any compound from benzimidazole derivatives Y-0 to Y-12 in prevention and treatment of agricultural plant diseases. It is found through bioactivity test that compounds have certain inhibition activity on six plant fungi including Phyllosticta zeae, botrytis cinerea, sclerotinia sclerotiorum, magnaporthe grisea, rhizoctonia solani and fusarium oxysporum, the inhibition rate of part of the compounds on the six pathogenic fungi under 100 ppm reaches 70% or above, and particularly, the growth of Phyllosticta zeae is almost completely inhibited. The compounds are simple to prepare and cheap and easily available in raw materials, and are expected to be developed into novel bactericides.

A step-by-step synthesis of triazole-benzimidazole-chalcone hybrids: Anticancer activity in human cells+

Novel series of triazole-benzimidazole-chalcone hybrid compounds have been synthesized via click chemistry, between different azide derivatives and substituted benzimidazole terminal alkynes bearing a chalcone moiety. The starting alkynes are prepared via base-catalysed nitrogen alkylation of pre-synthetized benzimidazole-chalcone substrates. All the intermediates as well as the final products are fully characterized by 1D and 2D NMR and mass spectrometry techniques. HMBC correlations permits the identification of a unique 1,4-disubstitued triazole-benzimidazole-chalcone isomer. Evaluation of the anti-proliferative potential in breast and prostate cancer cell lines showed that the presence of chloro substituents at the chalcone ring of the triazole-benzimidazole-chalcone skeleton enhanced the cytotoxic effects. The benzyl group linked to the 1,2,3-triazole moiety provides more antiproliferative potential.

Synthesis and characterization of novel benzimidazole embedded 1,3,5-trisubstituted pyrazolines as antimicrobial agents

Efficient syntheses of some new substituted pyrazoline derivatives linked to substituted benzimidazole scaffold were performed by multistep reaction sequences. All the synthesized compounds were characterized using elemental analysis and spectral studies (IR, 1D/2D NMR techniques and mass spectrometry). The synthesized compounds were screened for their antimicrobial activity against selected Gram-positive and Gram-negative bacteria, and fungi strain. The compounds with halo substituted phenyl group at C5 of the 1-phenyl pyrazoline ring (15, 16 and 17) showed significant antibacterial activity. Among the screened compounds, 17 showed most potent inhibitory activity (MIC = 64 μg mL-1) against a bacterial strain. The tested compounds were found to be almost inactive against the fungal strain C. albicans, apart from pyrazoline-1-carbothiomide 21, which was moderately active.

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.