54915-69-4

Upstream product

• 62-53-3 aniline 
• 2216-92-4 N-phenylglycine ethyl ester 
• 105-39-5 chloroacetic acid ethyl ester 
• 2258-42-6 formyl acetic anhydride 

Downstream Products

• 117121-07-0 diethyl 2-mercapto-1-phenylimidazole-4,5-dicarboxylate 
• 117121-01-4 diethyl 1-phenyl-1H-imidazole-4,5-dicarboxylate 
• 123017-50-5 1-phenyl-2-thioxo-2,3-dihydro-1H-imidazole-4,5-dicarboxylic acid 
• 857772-85-1 1-phenyl-1H-imidazole-4,5-dicarboxylic acid 

Relevant academic research and scientific papers

Bis(acyloxmethyl)imidazole compounds

This invention relates to new bis(acyloxymethyl)imidazole derivatives; to compositions comprising these derivatives; and to processes for their utility as fungicides, bactericides and as inhibitors of the growth of cancer, particularly solid tumor cancer, in warm blooded animals of the formula: STR1 wherein M is STR2 or R; each R, R' and R" are independently selected from hydrogen and Z substituted or unsubstituted alkyl, cycloalkyl, cycloalkenyl, alkenyl, aryl, and heterocyclic ring wherein said ring comprises at least one of oxygen, nitrogen, sulfur or silicon; provided that STR3 may form a Z substituted or unsubstituted heterocyclic, and R' and R" attached to the imidazole ring, may form a Z substituted or unsubstituted heterocyclic ring; X is selected from at least one of oxygen, sulfur, nitrogen and alkyl; provided further that silicon is not directly attached to oxygen, sulfur or nitrogen and R' is not hydrogen when X is oxygen or sulfur; and Z is selected from halogen, nitro, nitrile, alkyl, haloalkyl, alkenyl, carboxylic acid, carboxylic acid ester, carboxylic acid amide, ether, thioether, hydroxyl, acylated hydroxyl, sulfonylamide, sulfonylurea, sulfoxide, sulfone, substituted and unsubstituted amine or mixtures thereof.

Design, Synthesis, Antineoplastic Activity, and Chemical Properties of Bis(carbamate) Derivatives of 4,5-Bis(hydroxymethyl)imidazole

A series of bis(carbamate) derivatives of 1,2-substituted 4,5-bis(hydroxymethyl)imidazoles were prepared and evaluated against murine P388 lymphocytic leukemia.Electron-withdrawing substituents at either N-1 or C-2 gave rise to inactive compounds.However, electron-donating substituents gave active compounds and the 2-(methylthio)-1-methyl derivative 2i (carmethizole), as the bis(N-methylcarbamate), was found to be very active.The derivative 2i, referred to by the name carmethizole, was also shown to be active against the MX-1 mammary xenograft, the human amelanotic melanoma cell line (LOX) xenograft, the M5076 sarcoma, and L1210 lymphocytic leukemia.The solution stability, water solubility, pKa, and log P of carmethizole are also reported.