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Reinvestigation of the Nitration of Trichloroethene – Subsequent Reactions of the Products and Evaluation of Their Antimicrobial and Antifungal Activity
Author(s) -
Zapol'skii Viktor A.,
Namyslo Jan C.,
Sergeev Galina,
Brönstrup Mark,
Gjikaj Mimoza,
Kaufmann Dieter E.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501066
Subject(s) - chemistry , nitration , nitroethane , antimicrobial , medicinal chemistry , antifungal , methylene , nitro , stereochemistry , nuclear chemistry , organic chemistry , alkyl , medicine , dermatology , nitromethane
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(NO 2 )NRR 1 and R–O–N=C(Hal)NRR 1 , 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(1 H )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 IC 50 of 0.2 μg/mL.