32997-17-4

Upstream product

• 72615-38-4 (4Z)-2-(4-methylphenyl)-4-(phenylmethylidene)-1,3-oxazol-5(4H)-one 
• 874-60-2 4-methyl-benzoyl chloride 
• 27115-50-0 N-(4-methylbenzoyl)glycine 
• 100-52-7 benzaldehyde 
• 459-73-4 GlyOEt*HCl 
• 56108-06-6 p-toluimidic acid methyl ester 
• 623-33-6 glycine ethyl ester hydrochloride 
• 39739-50-9 p-toluimidic acid methyl ester hydrochloride 

Downstream Products

• 74084-23-4 N-(4-methylbenzoyl)phenylalanine 

Relevant academic research and scientific papers

Synthesis and biological testing of (5Z)-2-aryl-5-arylmethylidene-3,5-dihydro-4H-imidazol-4-ones as antimitotic agents

Compounds interacting with cell protein tubulin and microtubules represent an important type of antimitotic agents. A series of tubulin-targeted 2-aryl-4-benzoyl-imidazoles were reported to possess high cytotoxicity, and so, we prepared a series of structural isomers of these to be evaluated as antimitotic agents. The synthesis of the novel (Z)-2-aryl-5-arylmethylidene-3,5-dihydro-4H-imidazol-4-ones involved coupling of substituted hippuric acids with aromatic aldehydes. Subsequent conversion of the resulting oxazolones to the corresponding imidazolones was carried out under microwave irradiation in the presence of urea and ammonium acetate. The cytotoxicity of the majority of the compounds to human epithelial carcinoma cancer cell line A549 was in the sub-micromolar range and was found to be more sensitive to the substituents on the 5-arylmethylidene fragment than on the 2-aryl ring in general. The cytotoxicities of the synthesized compounds were lower than those of the previously reported isomeric 2-aryl-4-benzoyl-imidazoles, and the basic structure–activity relationships in the isomeric pairs were different. Synthesized (5Z)-5-[(4-bromophenyl)methylidene]-2-(4-methylphenyl)-3,5-dihydro-4H-imidazol-4-one, which had the highest cytotoxicity (IC50?~?440?nM) in the series of novel compounds, had a definite cytostatic effect on the A549 cells, but its antiproliferative properties were not linked to action on the microtubules. This would be an interesting lead compound for additional investigation into the mechanism of cytostatic action, and further structural optimization.

Synthesis of Acylamino Acids and Acylamino Acid Amides by Simultaneous Reduction and Hydrolysis of Unsaturated 2,4-Disubstituted 2-Imidazolin-5-ones

Twelve acylamino acids (II) and two acylamino acid amides (III) have been prepared by the simultaneous reduction and hydrolysis of unsaturated 2,4-disubstituted 2-imidazolin-5-ones (I) with a mixture of zinc dust and potassium hydroxide solution.

Synthesis of Acylamino Acid Amides and Acylamino Acids via 2,4-Disubstituted 2-Imidazolin-5-ones

Unsaturated 2,4-disubstituted 2-imidazolin-5-ones (I) have been reduced with a mixture of hydriodic acid and red phosphorus in the presence of acetic anhydride to give the saturated 2,4-disubstituted 2-imidazolin-5-ones (II) which have been hydrolysed to acylamino acid amides (III) and acylamino acids (IV) with sodium hydroxide solution under different conditions.In all six acylamino acid amides (23 - 51percent yields) and four acylamino acids (26 - 65percent yields) have been prepared.One saturated 2-imidazolin-5-one, namely 2-phenyl-4-benzyl-2-imidazolin-5-one has been isolated from the reaction in 40percent yield and identified.