77038-06-3

Upstream product

• 2327-99-3 1-phenylpropadiene 
• 533-58-4 2-Iodophenol 
• 201230-82-2 carbon monoxide 
• 506-59-2 N,N-dimethylammonium chloride 
• 67-63-0 isopropyl alcohol 
• 487-26-3 Flavanone 
• 50-00-0 formaldehyd 
• 33460-83-2 3-<(dimethylamino)methyl>flavanone hydrochloride 

Relevant academic research and scientific papers

Synthesis of quinol-4-ones and chroman-4-ones via a palladium-catalysed cascade carbonylation-allene insertion

Palladium(0)-catalysed termolecular queuing processes involving oxidative addition to aryl iodides followed by low pressure carbonylation, allene insertion and capture of the resulting π-allyl palladium(II) species by an internal O- or N-nucleophile occur in good yields. One-pot 3-methylene chromanone/quinolone synthesis-Michael addition-stereoselective reduction are also reported. (C) 2000 Elsevier Science Ltd.

Synthesis and Cytotoxic Evaluation of 3-Methylidenechroman-4-ones

In the search for new anticancer agents, a library of variously substituted 3-methylidenechroman-4-ones was synthesized using Horner–Wadsworth–Emmons methodology. Acylation of diethyl methylphosphonate with selected ethyl salicylates furnished 3-diethoxyphosphorylchromen-4-ones which were next used as Michael acceptors in the reaction with various Grignard reagents. The adducts were obtained as the mixtures of trans and cis diastereoisomers along with a small amount of enol forms. Their relative configuration and preferred conformation were established by NMR analysis. The adducts turned up to be effective Horner–Wadsworth–Emmons reagents giving 2-substituted 3-methylidenechroman-4-ones, which were then tested for their possible cytotoxic activity against two leukemia cell lines, HL-60 and NALM-6, and against MCF-7 breast cancer cell line. All new compounds (14a–o) were highly cytotoxic for the leukemic cells and showed a moderate or weak effect on MCF-7 cells. Analog 14d exhibited the highest growth inhibitory activity and was more potent than carboplatin against HL-60 (IC50 = 1.46 ± 0.16 μM) and NALM-6 (IC50 = 0.50 ± 0.05 μM) cells. Further tests showed that 14d induced apoptosis in NALM-6 cells, which was mediated mostly through the extrinsic pathway.

3-Methylene flavanones and 3-methylene chromanones

Compounds which are 3-methylene flavanones and 3-methylene chromanones having activity against microorganisms are disclosed. The compounds are represented by the general structural formula: STR1 wherein: R1 is a member selected from the group consisting of hydrogen, Br, CH3 and OCH3 ; R2 is selected from the group consisting of hydrogen and STR2 wherein R4 is a member selected from the group consisting of hydrogen, Br, Cl, CH3, OCH3, NO2, N(CH3)3 and CN; R5 is selected from the group consisting of hydrogen and Cl, with the proviso that when R5 is Cl, R4 is hydrogen or Cl; and R3 is selected from the group consisting of hydrogen, phenyl, 2-thienyl, 4-pyridyl and naphthyl, with the proviso that when R3 is naphthyl, R1 and R2 are hydrogen.