515824-31-4

Basic information

• Product Name: 1-(1H-benzimidazol-2-yl)-3-(4-methoxyphenyl)-2-propen-1-one
• Synonyms: 1-(1H-benzimidazol-2-yl)-3-(4-methoxyphenyl)-2-propen-1-one
• CAS NO: 515824-31-4
• Molecular Formula: C₁₇H₁₄N₂O₂
• Molecular Weight: 278.30526
• Mol File: 515824-31-4.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(1H-benzimidazol-2-yl)-3-(4-methoxyphenyl)-2-propen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1H-benzimidazol-2-yl)-3-(4-methoxyphenyl)-2-propen-1-one(515824-31-4)
• EPA Substance Registry System: 1-(1H-benzimidazol-2-yl)-3-(4-methoxyphenyl)-2-propen-1-one(515824-31-4)

Safety Data

• Hazardous Substances Data: 515824-31-4(Hazardous Substances Data)

Upstream product

• 16414-04-3 1-benzimidazol-2-ylethanol 
• 95-54-5 1,2-diamino-benzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 939-70-8 2-acetylbenzimidazole 

Downstream Products

• 670749-98-1 (E)-3-(4-methoxyphenyl)-1-(1-methyl-1H-benzimidazol-2-yl)-2-propen-1-one 
• 132308-71-5 4-(benzimidazol-2-yl)-6-(4-methoxyphenyl)pyrimidin-2-amine 
• 63330-75-6 2-[5-(4-methoxyphenyl)-1-phenyl-4,5-dihydro-1H-3-pyrazolyl]-1H-benzimidazole 
• 63330-82-5 2-[5-(4-methoxyphenyl)-4,5-dihydroisoxazol-3-yl]benzimidazole 
• 1417372-99-6 5-[(2E)-1-(1H-benzimidazol-2-yl)-3-(4-methoxyphenyl)prop-2-en-1-ylidene]pyrimidine-2,4,6-(1H,3H,5H)-trione 
• 132308-54-4 2-<5-(p-anisyl)-4,5-dihydropyrazol-3-yl>benzimidazole 
• 630102-72-6 4-(1-benzyl-1H-benzoimidazol-2-yl)-2-(4-methoxy-phenyl)-2,3-dihydro-benzo[b][1,4]thiazepine 
• 630102-59-9 4-(1H-benzoimidazol-2-yl)-2-(4-methoxy-phenyl)-benzo[b][1,4]thiazepine 
• 630102-67-9 2-(4-methoxy-phenyl)-4-(1-methyl-1H-benzoimidazol-2-yl)-2,3-dihydro-benzo[b][1,4]thiazepine 

Relevant articles and documents

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.

Design and synthesis of benzimidazole-chalcone derivatives as potential anticancer agents

Numerous reports have shown that conjugated benzimidazole derivatives possess various kinds of biological activities, including anticancer properties. In this report, we designed and synthesized 24 new molecules comprising a benzimidazole ring, arene, and alkyl chain-bearing cyclic moieties. The results showed that the N-substituted benzimidazole derivatives bearing an alkyl chain and a nitrogen-containing 5- or 6-membered ring enhanced the cytotoxic effects on human breast adenocarcinoma (MCF-7) and human ovarian carcinoma (OVCAR-3) cell lines. Among the 24 synthesized compounds, (2E)-1-(1-(3-morpholinopropyl)-1H-benzimidazol-2 -yl)-3-phenyl-2-propen-1-one) (23a) reduced the proliferation of MCF-7 and OVCAR-3 cell lines demonstrating superior outcomes to those of cisplatin.

Ultrasound accelerated synthesis of novel benzimidazole derived chalcones as glucosidases inhibitor and antimicrobial agents

A novel series of 3-substituted-1-[1-(toluene-4-sulfonyl)-1H-benzoimidazol-2-yl]-propen-1-one 3a-m have been synthesized by tosylation of benzimidazole chalcones 2a-m using ultrasound in lesser time with higher yields. All the synthesized compounds have been characterized by IR, 1H and 13C NMR, mass and elemental analysis in full accordance with their depicted structure. Biological evaluation of the compounds 3a-m reveals that compound 3f shows moderate inhibition of glucoamylase and compound 3i exhibits compelling inhibition of α-amylase. Compound 3k and 3d display excellent antibacterial activity against all tested strains and admirable antifungal activity against Candida albicans respectively in comparison to the standards. The results of biological study show that introduction of tosyl group in benzimidazole chalcones enhances the inhibition of glycosidases and microorganism in comparison to parent compounds.