“…In the course of our research interest ( Meier et al , 2012 ; Sá, 2003 ; Sá et al , 2007 ) in the chemistry of Morita-Baylis-Hillman (MBH) adducts ( Basavaiah et al , 2010 ; Basavaiah and Veeraraghavaiah, 2012 ; Singh and Batra, 2008 ) and the antimicrobial activity of synthetic derivatives ( Silveira et al , 2012 ), we have been able to readily install the S-C-N framework through chemical synthesis in aqueous medium under mild conditions to give the corresponding allylic isothiouronium salts or thiocyanates in excellent yields. Herein, we present our results for the screening of a family of allylic thiocyanates against bacteria and fungi strains with a view to developing novel antibiotic agents.…”
Bacterial resistance to commonly used antibiotics has been recognized as a significant global health issue. In this study, we carried out the screening of a family of allylic thiocyanates for their action against a diversity of bacteria and fungi with a view to developing new antimicrobial agents. Allylic thiocyanates bearing halogenated aryl groups, which were readily obtained in two steps from the Morita-Baylis-Hillman adducts, showed moderate-to-high activity against selective pathogens, including a methicillin-resistant S. aureus (MRSA) strain. In particular cases, methyl (Z)-3-(2,4-dichlorophenyl)-2-(thiocyanomethyl)-2-propenoate exhibited antimicrobial activity comparable to the reference antibiotic Imipenem.
“…In the course of our research interest ( Meier et al , 2012 ; Sá, 2003 ; Sá et al , 2007 ) in the chemistry of Morita-Baylis-Hillman (MBH) adducts ( Basavaiah et al , 2010 ; Basavaiah and Veeraraghavaiah, 2012 ; Singh and Batra, 2008 ) and the antimicrobial activity of synthetic derivatives ( Silveira et al , 2012 ), we have been able to readily install the S-C-N framework through chemical synthesis in aqueous medium under mild conditions to give the corresponding allylic isothiouronium salts or thiocyanates in excellent yields. Herein, we present our results for the screening of a family of allylic thiocyanates against bacteria and fungi strains with a view to developing novel antibiotic agents.…”
Bacterial resistance to commonly used antibiotics has been recognized as a significant global health issue. In this study, we carried out the screening of a family of allylic thiocyanates for their action against a diversity of bacteria and fungi with a view to developing new antimicrobial agents. Allylic thiocyanates bearing halogenated aryl groups, which were readily obtained in two steps from the Morita-Baylis-Hillman adducts, showed moderate-to-high activity against selective pathogens, including a methicillin-resistant S. aureus (MRSA) strain. In particular cases, methyl (Z)-3-(2,4-dichlorophenyl)-2-(thiocyanomethyl)-2-propenoate exhibited antimicrobial activity comparable to the reference antibiotic Imipenem.
“…Multifunctional allylic bromides such as the title compound, (I), are versatile building blocks for the stereoselective construction of natural products and heterocycles of biological relevance (Drewes & Emslie, 1982;Hoffmann & Rabe, 1985;Cheskis et al, 1990;Roush & Brown, 1993;Basavaiah & Hyma, 1996;Grassi et al, 1997;Mateus et al, 2001;Fernandes et al, 2004). Preparation of allylic bromide (I) can be achieved in good yield and excellent stereoselectivity by treating the corresponding -methylene--hydroxy ester (II) (a Baylis-Hillman adduct) (Basavaiah et al, 2003;Ciganek, 1997;Sá , 2003;Hoffmann & Buchholz, 1991) with a combination of HBr and H 2 SO 4 , as previously reported (Fernandes et al, 2004). Careful crystallization from hexane-ethyl acetate (9:1) furnished colourless crystals (m.p.…”
Key indicatorsSingle-crystal X-ray study T = 293 K Mean (C-C) = 0.005 Å R factor = 0.039 wR factor = 0.111 Data-to-parameter ratio = 14.0For details of how these key indicators were automatically derived from the article, see
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.