Synthesis, characterization and bioactivity determination of ferrocenyl urea derivatives

Abstract

Fourteen new ferrocene derivatives containing urea linker were synthesized from the reaction of ferrocenecarbonyl azide with aromatic amines. The structures of the synthetic compounds were confirmed by 1H NMR, 13C NMR, IR, mass spectrometry and elemental analysis. These organometallic compounds were evaluated by in vitro protease assay using fluorogenic substrate peptide, and several showed potent inhibition against HIV‐1 protease. Copyright © 2012 John Wiley & Sons, Ltd.

Synthesis of Ferrocene Derivatives Allowing Linear Free Energy Studies of Redox Potentials

“…[10] The acid was also converted to the acyl azide and the corresponding urea 3 by means of a Curtius rearrangement. [21] Another precursor, aminoferrocene, was converted to the corresponding primary amine intermediate 8 under S N 2 reaction conditions. [22] Subsequent methylation with methyl iodide gave 4.…”

Synthesis of 3-Trifluoromethyl-5,6-dihydro-[1,2,4]triazolo Pyrazine Derivatives and Their Anti-Cancer Studies

“…Though various reports are available in the literature for the synthesis of pyrazine derivatives (RB), there is no method available to access them under mild reaction conditions with an excellent yield, which inspired us to focus our efforts in this direction. In order to execute our idea, we have treated 3-trifluoromethyl-5,6,7,8-tetrahydro- [1,2,4]triazolo [4,3-α]pyrazine hydrochloride with 1-chloromethyl-4-iso-cyanato benzene under the catalytic influence of Et 3 N in DCM at room temperature, over a period of 5 h. This produced the anticipated product in a 92% yield (Scheme 1). The structure of the molecule was confirmed by 1 H-NMR, IR, and LCMS analyses.…”

“…The solvent was evaporated and the crude product was purified by column chromatography over silica gel using chloroform: methanol (9:1) as an eluent to afford the anticipated products (RB1-RB9) (Supplementary Materials). [1,2,4]triazolo [4,3-α] [1,2,4]triazolo [4,3-α]pyrazine-7(8H)carboxamide (RB2): (95%, off-white-solid), 188.6-205.9 °C, 1 H-NMR (CDCl3, 400 MHz) δ: 4.07 (t, 2H, J = 5.6 Hz), 4.27 (t, 2H, J = 5.6 Hz), 5.02 (s, 2H), 6.90-7.58 (m, 10H). LCMS for C19H16F3N5O MS (ESI + ion): m/z = 388 [M + H] + .…”

Solution Conformation and Self‐Assembly of Ferrocenyl(thio)ureas

“…However, the solid‐state structure of 1 has only recently been published . Compounds of this type find applications as anion sensors and as host–guest receptors,, , as labels for oligonucleotides, and for potential pharmaceutical uses , . Electronic communication between two redox‐equivalent ferrocenyl centers through hydrogen‐bonded urea units in a hydrogen‐bonded dimer has been investigated .…”