39185-89-2Relevant articles and documents
Reinvestigation of the nitration of trichloroethene - Subsequent reactions of the products and evaluation of their antimicrobial and antifungal activity
Zapol'Skii, Viktor A.,Namyslo, Jan C.,Sergeev, Galina,Br?nstrup, Mark,Gjikaj, Mimoza,Kaufmann, Dieter E.
, p. 7763 - 7774 (2015)
The nitration reaction of trichloroethene (1) to main products trichloronitroethene (TCNiE 2, up to 60.8 %, by GC), 1,1,2,2-tetrachloro-1-nitroethane (8, up to 25.1 %, by GC), and 1,2,2-trichloro-2-nitroethyl [chloro(nitro)methylene]azinate (9, up to 8.0 %, by GC) was comprehensively investigated and optimized. Different 1,1-diamino-2-chloro-2-nitroethenes, 2-nitroethoxyguanidines, and rare O-(1,2,2-trichloro-2-nitroethyl) oximes and carbimidoyl halides with unique formulas R-O-N=C(NO2)NRR1 and R-O-N=C(Hal)NRR1, respectively, were obtained from these nitration products in yields up to 91 %. The structure of (E)-morpholino(nitro)methanone O-(1,2,2-trichloro-2-nitroethyl) oxime (19) was proven by single-crystal X-ray diffraction analysis. In addition, the antimicrobial and antifungal activity of the synthesized compounds was examined. Notably, N-(1,2,2-trichloro-2-nitroethoxy)-3,4-dihydroisoquinoline-2(1H)carbimidoyl chloride (27) inhibited the growth of methicillin-resistant and sensitive Staphylococcus aureus with minimum inhibitory concentrations of 1.3 μg mL-1, and reduced the viability of the MCF-7 cancer cell line with an IC50 of 0.2 μg/mL. Trichloronitroethene and 1,2,2-trichloro-2-nitroethyl [chloro(nitro)methylene]azinate, nitration products of trichloroethene, are buildings blocks for O-(1,2,2-trichloro-2-nitroethyl) oximes, 1,1-diamino-2-chloro-2-nitroethenes, 2-nitroethoxyguanidines, and carbimidoyl halides. Some compounds show high activity against Staphylococcus aureus and reduce the viability of the MCF-7 cancer cell lines.
