Nitroimidazoles as chemotherapeutic agents

Synthesis and characterization of 1‐methyl‐2,4,5‐trinitroimidazole (MTNI)

“…The crystal structure of compound 1 was found to be orthorhombic, which belongs to space group Pca2 1 with crystallographic parameters of a=8.6183(6) Å, b= 17.7119(12) Å, c=10.6873(7) Å, V=1631.38(19) Å 3 , M = 217.11, Z=8, µ=0.167 -1 mm, F(000)=880 and D c =1.768 g/cm 3 . The unit cell parameters were refined by a least-squares fit of the setting angles of 20 reflections in the range 0<θ<28°.…”

“…The resultant ether solution was dried and evaporated to give 1.57 g of 1-methyl-2,4,5-trinitroimidazole (36 %). The structure was confirmed with DSC, 1 H-and 13 C-NMR, CHN analysis, and X-ray crystallography; mp 82 °C (on DSC); A yellow crystal of 1, grown in ethanol solution at room temperature, of approximate dimensions 0.45×0.50×0.56 mm 3 , was used for data collection. Diffraction experiment was performed on a Bruker SMART diffractometer equipped with a CCD area detector using Mo K α radiation (λ=0.71073 Å).…”

“…The density value measured by Archimedes method from the crystal of 1 at 25 °C is 1.752 g/cm 3 . According to our experimental result, the density of 1 is higher than that of Comp B, but slightly lower than that of RDX.…”

Structure du 2,3-diméthyl-3-(1,2-diméthylimidazol-4-yl)butan-2-ol

“…Les 5-nitroimidazoles reprtsentent une famille de mtdicaments d'une grande importance dans le traitement de l'amibiase, de la trichomonase et des infections dues aux bact&ies ana&obies (Nair & Nagarajan, 1983). Au cours de nos 6tudes ax6es sur la compr6hension de leurs propri6t6s biologiques dues ~ leur activation par r6action de transfert mono61ectronique, il a +t+ montr6 (Crozet, Vanelle, Jentzer & Bertrand, 1989) que l'anion du 2-nitropropane r6agissait avec le 1,2-dim6thyl-5-nitroimidazole (Emtryl®) pour conduire au d6riv6 nitr6 tertiaire (I).…”

A novel synthesis for new substituted imidazoles

“…The pharmacological interest of the imidazole ring has been established, Nitroimidazoles being extensively used in therapy against amoebic, trichomonal, giardial and anaerobic infections, or as hypoxic cell radiosensitizers [2]. Metronidazole and substituted imidazoles (ketoconazole, fluconazole and itraconazole) are well-tolerated drugs that are potentially active against Leishmania, but their use in the treatment of cutaneous and visceral leishmaniasis has produced conflicting results [3].…”