138469-47-3

Upstream product

• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 13745-26-1 (E)‐1‐(2‐hydroxy‐4‐methoxyphenyl)‐3‐(3,4,5‐trimethoxyphenyl)prop‐2‐en‐1‐one 

Downstream Products

• 99100-14-8 7-methoxy-2-(3,4,5-trimethoxy-phenyl)-chroman-4-ol 
• 100211-06-1 baptigenin trimethyl ether 
• 138469-52-0 C₂₆H₂₇NO₈S 

Relevant academic research and scientific papers

Synthesis of isoflavones containing naturally occurring substitution pattern by oxidative rearrangement of respective flavanones using thallium(III) p-tosylate

Claisen condensation of substituted 2′-hydroxyacetophenones 1a-c with aromatic aldehydes affords respective substituted 2′-hydroxychalcones 2a-n which on base catalyzed cyclization in pyridine:methanol:water (1:1:1) give respective flavanones 3a-n. The oxidative rearrangement of flavanones with thallium(III) p-tosylate furnishes respective isoflavones 4a-n in overall 62-72% yields starting from 1. The present methodology has been successfully applied for the synthesis of naturally occurring isoflavones such as di-O-methyldaidzein 4a, cabruvin 4b, pseudobabtigenin methylether 4d, 5,7-dimethoxyisoflavone 4f, 5,7,4′-trimethoxyisoflavone 4g, derrustone 4i, 7,8,3′,4′- tetramethoxyisoflavone 41, purpuranin-A 4m and 7,8,3′,4′,5′- pentamethoxyisoflavone 4n and thus the first synthesis of 4n is reported.

Novel chromene derivatives as TNF-α inhibitors

A novel series of chromene-based TNF-α inhibitors is described. These chromene derivatives inhibit bacterial lipopolysaccharide (LPS) stimulated production of TNF-α from human peripheral blood mononuclear cells (PBMC). Additionally, these compounds inhibit NF-kB mediated transcription activation.

Synthesis and aromatase inhibitory activity of flavanones

Purpose. Aromatase inhibitors are known to prevent the conversion of androgens to estrogens and play a significant role in the treatment of estrogen dependent diseases such as breast cancer. Some flavonoids have been reported as potent aromatase inhibitors; therefore, in an effort to develop novel anti breast cancer agents, B ring substituted flavanones with a 7-methoxy group on A ring were synthesized and tested to assess their ability to inhibit aromatase activity and to determine the optimal B ring substitution pattern. Methods. A series of flavanones was prepared by cyclisation of 2′hydroxychalcones previously obtained by Claisen-Schmidt condensation and the aromatase inhibitory activity of these compounds was investigated using human placental microsomes and radiolabeled [1,2,6,7-3H]-androstenedione as substrate. Results. Almost all flavanones exhibited inhibitory effect on the aromatase activity but their potency was dependent on their B ring substitution pattern. Hydroxylation at position 3′ and/or 4′ enhanced the anti-aromatase activity; thus, 3′,4′-dihydroxy-7-methoxyflavanone was found to be twice more potent than aminoglutethimide, the first aromatase inhibitor clinically used. Conclusions. These results indicated that these flavanones could be considered as potential anti breast cancer agents through the inhibition of aromatase activity and allowed us to select some of these compounds as skeleton for the development of flavonoid structurally-related aromatase inhibitors.

An improved procedure for flavanones

Trifluoroacetic acid is found to be an efficient reagent for the isomerisation of chalcones to flavanones.