159763-36-7Relevant articles and documents
Baylis-Hillman reactions in aqueous acidic media
Caumul, Prakashanand,Hailes, Helen C.
, p. 8125 - 8127 (2005)
The Baylis-Hillman reaction has been successfully performed under aqueous acidic conditions at pH 1, using a range of substrates and tertiary amines as catalysts.
New allyldithiocarbimate salts: Synthesis, structure and antifungal activity
Albuini-Oliveira, Nathália M.,Alvarez, Natalia,Ellena, Javier,Guilardi, Silvana,Lima, Marcelo S.,Rubinger, Mayura M. M.,Souza, Rafael A. C.,Tavares, Eder C.,Vidigal, Antonio E. C.,Zacchi, Carlos H. C.,Zambolim, Laercio
, (2020/04/21)
Fifteen new allyldithiocarbimates were prepared from different allylic bromides and various potassium dithiocarbimates, yielding (Z)-2-(methoxycarbonyl)-3-(X-nitrophenyl)allyl-(N-R-sulfonyl)dithiocarbimates (where X = 2, 3 and 4; R = phenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl and 4-iodophenyl). These anions were isolated as tetraphenylphosphonium salts and characterized by HRMS, infrared, 1H and 13C NMR spectroscopies. Molecular electrostatic potentials were used to evaluate intermolecular interactions present in the new substances and to explain variations observed on their melting points. Single crystal X-ray diffraction experiments confirmed the Z stereochemistry of the allyldithiocarbimate anions. C–H?O, C–H?N, C–H?S and C–H?π intermolecular interactions in the solid state were studied by X-ray diffraction and Hirshfeld surface analyses. The new compounds inhibited the mycelial growth of various fungi species responsible for severe plant diseases. The allylithiocarbimates were especially active against Botrytis cinerea, with IC50 values as low as 20 μM, being more effective than the active principals of the commercial fungicides Ziram and Mancozeb.
Exploratory applications of 2-nitrobenzaldehyde-derived Morita–Baylis–Hillman adducts as synthons in the construction of drug-like scaffolds
Idahosa, Kenudi C.,Davies-Coleman, Michael T.,Kaye, Perry T.
, p. 417 - 430 (2019/01/24)
Morita–Baylis–Hillman adducts, prepared from 2-nitrobenzaldehyde precursors and either methyl acrylate or methyl vinyl ketone, have been used as critical synthons in the preparation of α-[(alkylamino)methyl]cinnamate esters and their but-3-en-2-one analogs, cinnamate ester-azidothymidine (AZT) conjugates, 2-quinolone and quinoline derivatives. Computer docking studies have been conducted to explore the potential of the cinnamate ester–AZT conjugates as potential dual-action HIV-1 integrase–reverse transcriptase (IN–RT) inhibitors. The results further demonstrate the applicability of Morita–Baylis–Hillman methodology in the construction of complex drug-like scaffolds.
