129409-96-7Relevant academic research and scientific papers
Trypanocidal activity of flavanone derivatives
Andrade, Josimara Souza,Diogo, Gabriela Maciel,Dos Santos, Viviane Martins Rebello,Murta, Silvane Maria Fonseca,Sales, Policarpo Ademar,Taylor, Jason Guy
, (2020)
Chagas disease, also known as American trypanosomiasis, is classified as a neglected disease by the World Health Organization. For clinical treatment, only two drugs have been on the market, Benznidazole and Nifurtimox, both of which are recommended for use in the acute phase but present low cure rates in the chronic phase. Furthermore, strong side effects may result in discontinuation of this treatment. Faced with this situation, we report the synthesis and trypanocidal activity of 3-benzoyl-flavanones. Novel 3-benzoyl-flavanone derivatives were prepared in satisfactory yields in the 3-step synthetic procedure. According to recommended guidelines, the whole cell-based screening methodology was utilized that allowed for the simultaneous use of both parasite forms responsible for human infection. The majority of the tested compounds displayed promising anti-Trypanosoma cruzi activity and the most potent flavanone bearing a nitrofuran moiety was more potent than the reference drug, Benznidazole.
Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones
Clarke, David S.,Gabbutt, Christopher D.,Hepworth, John D.,Heron, B. Mark
, p. 5515 - 5519 (2007/10/03)
3-Acylchromones and 3-acylflavones, readily available by acylation of 2′-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO 3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones.
CONJUGATE ADDITION OF CUPRATE REAGENTS TO CHROMONES: A ROUTE TO 2-SUBSTITUTED CHROMAN-4-ONES
Saengchantara, Suthiweth T.,Wallace, Timothy W.
, p. 3029 - 3036 (2007/10/02)
Chromones (4-oxo-4H-1-benzopyrans) activated by electron-withdrawing groups attached to C-3 undergo efficient 1,4-addition of cuprate reagents, producing 2,3-disubstituted chroman-4-ones.The addition products from methyl chromone-3-carboxylates can be converted into 2-substituted chroman-4-ones by treatment with sodium chloride in wet dimethylsulphoxide.
CONJUGATE ADDITION TO CHROMONES: SYNTHESIS OF SUBSTITUTED 4-CHROMANONES
Wallace, Timothy W.
, p. 4299 - 4302 (2007/10/02)
Chromones activated by carbonyl substituents at C-3 are transformed into the corresponding 2-methyl-4-chromanones by treating with lithium dimethylcuprate.
