101681-92-9Relevant articles and documents
Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides
Cizek, Alois,Hosek, Jan,Jampilek, Josef,Kavanova, Lenka,Kos, Jiri,Lelakova, Veronika,Leva, Lenka,Michnova, Hana,Oravec, Michal,Pindjakova, Dominika,Strakova, Nicol,Strharsky, Tomas,Vrablova, Lucia
, (2022/03/19)
A series of eighteen 4-chlorocinnamanilides and eighteen 3,4-dichlorocinnamanilides were designed, prepared and characterized. All compounds were evaluated for their activity against gram-positive bacteria and against two mycobacterial strains. Viability on both cancer and primary mammalian cell lines was also assessed. The lipophilicity of the compounds was experimentally determined and correlated together with other physicochemical properties of the prepared derivatives with biological activity. 3,4-Dichlorocinnamanilides showed a broader spectrum of action and higher antibacterial efficacy than 4-chlorocinnamanilides; however, all compounds were more effective or comparable to clinically used drugs (ampicillin, isoniazid, rifampicin). Of the thirty-six compounds, six derivatives showed submicromolar activity against Staphylococcus aureus and clinical isolates of methicillin-resistant S. aureus (MRSA). (2E)-N-[3,5-bis(trifluoromethyl)phe-nyl]-3-(4-chlorophenyl)prop-2-enamide was the most potent in series 1. (2E)-N-[3,5-bis(Trifluoro-methyl)phenyl]-3-(3,4-dichlorophenyl)prop-2-enamide, (2E)-3-(3,4-dichlorophenyl)-N-[3-(trifluo-romethyl)phenyl]prop-2-enamide, (2E)-3-(3,4-dichloro-phenyl)-N-[4-(trifluoromethyl)phe-nyl]prop-2-enamide and (2E)-3-(3,4-dichlorophenyl)-N-[4-(trifluoromethoxy)phenyl]prop-2-en-amide were the most active in series 2 and in addition to activity against S. aureus and MRSA were highly active against Enterococcus faecalis and vancomycin-resistant E. faecalis isolates and against fast-growing Mycobacterium smegmatis and against slow-growing M. marinum, M. tuberculosis non-hazardous test models. In addition, the last three compounds of the above-mentioned showed insignificant cytotoxicity to primary porcine monocyte-derived macrophages.
Synthesis of Linear α,β-Unsaturated Amides from Isocyanates and Alkenylaluminum Reagents
Chen, Bo,Wu, Xiao-Feng
supporting information, p. 788 - 792 (2020/05/19)
A new approach has been developed for the synthesis of linear α,β-unsaturated amides by the direct coupling of isocyanates with alkenylaluminum reagents. At room temperature, the desired α,β-unsaturated amides were isolated in good to excellent yields with good functional-group tolerance in the absence of any catalyst or additive.
Copper-catalyzed direct transformation of secondary allylic and benzylic alcohols into azides and amides: An efficient utility of azide as a nitrogen source
Rokade, Balaji V.,Gadde, Karthik,Prabhu, Kandikere Ramaiah
, p. 2706 - 2717 (2015/04/27)
A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has been successfully adapted to the preparation of azides directly from their corresponding alcohols and offers excellent chemoselectivity in the formation of ω-halo azides and the azidation of allylic alcohols in the presence of a benzyl alcohol moiety. In addition, this strategy provides an opportunity to synthesize azides that can serve as precursors to β-amino acids. A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has also been adapted to the preparation of azides directly from their corresponding alcohols.
