64125-32-2

Upstream product

• 71686-61-8 7-(1,1-dimethyl-prop-2-ynyloxy)-2-phenyl-chromen-4-one 
• 24672-84-2 6-acetyl-5-hydroxy-2,2-dimethylchromene 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 1453164-95-8 (2Z)-3-hydroxy-1-(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-3-phenylprop-2-en-1-one 
• 115-18-4 2-methyl-3-buten-2-ol 
• 53258-99-4 7-hydroxy-8-(3-methylbut-2-en-1-yl)-2-phenylchroman-4-one 
• 6665-86-7 7-hydroxyflavone 
• 885118-28-5 5-hydroxy-2,2-dimethyl-2H-chromene-6-carboxylic acid ethyl ester 
• 885118-29-6 1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-2-methanesulfinylethanone 
• 100-52-7 benzaldehyde 
• 484-15-1 (-)-isolonchocarpin 

Relevant academic research and scientific papers

A new route to the synthesis of pyranoflavone and pyranochalcone natural products and their derivatives

The total synthesis of biologically active pyranoflavone natural products 1 and 2 was carried out starting from 2H-pyran. The synthesis of pyranochalcone natural products, lonchocarpin (9) and 4-hydroxylonchocarpin (10), and their derivatives 30-32 is des

New synthetic approaches to naturally occurring and unnatural pyranoflavones

Total synthesis of biologically interesting natural and unnatural pyranoflavones has been accomplished starting from readily available 2,4-dihydroxyacetophenone or 2,4-dihydroxy-6-methoxyacetophenone in three steps, i.e., benzopyran formation, condensatio

Anti-AIDS agents. 60. Substituted 3′R,4′R-di-O-(-)-camphanoyl- 2′,2′-dimethyldihydropyrano[2,3-f]chromone (DCP) analogues as potent anti-HIV agents

Synthesis of positional isomers is a commonly used technique in drug design. Accordingly, based on prior SAR studies of 3′R,4′R-di-O-(S)- camphanoyl-(+)-cis-khellactone (DCK, 1) analogues, a series of mono- and disubstituted chromone derivatives of 3′R,4′R-di-O-(-)camphanoyl- 2′,2′-dimethyldihydropyrano[2,3-f]chromone (DCP, 4) were designed and synthesized. Together with 1 and 4-methyl DCK (2), all newly synthesized DCP analogues (4-21) were screened for anti-HIV-1 activity against a non-drug-resistant strain in H9 lymphocytes and a multiple reverse transcriptase (RT) inhibitor-resistant strain in the MT4 cell line. Several DCP analogues (4, 5, 7, 8, 13, and 17) exhibited extremely high anti-HIV activity in the nondrug-resistant strain assay, with EC50 values ranging from 0.00032 to 0.0057 μM and remarkable therapeutic indexes (TI) ranging from 5.6 × 103 to 1.16 × 105, which were similar to those of 2 (EC50 0.0059 μM, TI > 6.6 × 103) and better than those of 1 (EC50 0.049 μM, TI > 328). Even more promisingly, some DCP analogues also showed activity against a multi-RT inhibitor-resistant strain, HIV-1 RTMDR1, whereas most DCK analogues did not. The most significant compound was 8, with an EC50 value of 0.06 μM and TI of 718 against the multi-RT inhibitor-resistant HIV-1 strain. Compounds 9 and 10 also showed good activity with an EC50 value of 0.14 μM, and TIs of 272 and >111, respectively. 2-Ethyl DCP (8) exhibited the best anti-HIV activity in both assays. Further development of 8-related compounds as clinical trial candidates is warranted.

New Syntheses of Ovaliflavanone-A, Ovaliflavanone-B and Ovalichromene-B

Nuclear prenylation of 7-hydroxyflavanone using 2-methyl-but-3-en-2-ol in the presence of BF3-etherate yields ovaliflavanone-A (II), ovaliflavanone-B (V), 7-hydroxy-6-C-prenylflavanone (IV) and 7-(γ,γ-dimethylallyloxy)-flavanone (III).Nuclear prenylation of 7-hydroxy-3',4'-methylenedioxyflavanone has earlier been shown to yield four products, viz.XI, XII, XIII and XIV.One of them, viz. 7-hydroxy-3',4'-methylenedioxy-8-C-prenylflavanone (XIV) with DDQ furnishes ovalichromene-B (XV).Some of the prenylated compounds from the above flavanones when subjected to DDQ treatment furnish new chromenoflavanones, chromenoflavones and isolonchocarpin.