Design, synthesis, antineoplastic activity, and chemical properties of bis(carbamate) derivatives of 4,5-bis(hydroxymethyl)imidazole

Abstract

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.

Synthesis and in vitro antiplatelet aggregation screening of novel fluorinated diethyl-2-(benzylthio)-2,3-dihydro-1H-imidazole-4,5-dicarboxylate derivatives

“…The contents of the flask were heated to 50-55°C, after which triethylamine (0.134 mol, 18.66 mL) was added, and the contents refluxed for 24 h. The solution was then cooled and filtered with Celite. The pure compound was obtained by completely distilling the filtrate to obtain N-formylglycine ethyl Preparation of sodium 1,2-bis-ethoxycarbonyl-2-formylamino-ethenolate (4) and diethyl 2-mercapto-4,5-imidazoledicarboxylate (5) The procedures in Jones (1952) and Anderson et al (1989) were adapted and modified. In a dry 2L three-necked flask provided with a stirrer, dropping funnel and reflux condenser, 80 mL of anhydrous ether and 3.2 g (1.25 g per piece) of clean sodium were placed.…”

Crystal structure of 2,4,5-tribromo-1-methyl-1H-imidazole, C4H3Br3N2

“…The imidazole core is akey for ahuge variety of important biologically active substances. It has found many applications in metalcarbene catalysts and is most important in ionic liquids (ILs) and magnetic ILs [3][4][5][6][7][8]. Polybrominated imidazole building blocks are useful as starting materials in the synthesis of very dense halogenated ILs [9].…”

N‐ and C‐acyclic thionuleoside analogues of 1,2,3‐triazole

“…However, con- + . Recent studies showed that some carbamates [39,40] exhibited in vitro potential antineoplastic activity against HL-60 human leukaemia and HT-29 human colon carcinoma cells. These findings prompted us to use the alcohol 6 to synthesize new, promising potential carbamates.…”