31525-76-5

Upstream product

• 31525-75-4 5-hydroxy-8,8-dimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2-one 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 32023-43-1 7-(1,1-dimethyl-prop-2-ynyloxy)-5-methoxy-chromen-2-one 
• 31525-67-4 dimethylacetal of 3-methyl-3-hydroxybutyraldehyde 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 108-73-6 3,5-dihydroxyphenol 
• 93929-73-8 5-hydroxy-8,8-dimethyl-9,10-dihydropyrano[2,3-f]chromen-2(8H)-one 
• 29373-14-6 2,2-dimethylchromane-5,7-diol 
• 76256-29-6 5,7-diacetoxy-8-(3'-methyl-2'-butenyl)coumarin 
• 2732-18-5 5,7-dihydroxy-2H-chromen-2-one 
• 3067-10-5 7-hydroxy-5-methoxychromene-2-one 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 53017-21-3 5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one 

Relevant academic research and scientific papers

A catalyst-free one-pot construction of skeletons of 5-methoxyseselin and alloxanthoxyletin in water

In refluxing water and without an additional catalyst, electron-rich phenols could react with alkynoic acids or alkynoates to provide coumarin structures. The skeletons of two natural pyranocoumarins, 5-methoxyseselin and alloxanthoxyletin, could be constructed (total yield up to 76%) in an aqueous multicomponent reaction in which isoprenyl acetate, propiolic acid, and phloroglucinol were simply mixed and refluxed in water.

Natural and synthetic 2,2-dimethylpyranocoumarins with antibacterial activity

A new efficient synthetic approach to the natural coumarins 5-hydroxyseselin (5), 5-methoxyseselin (3), and (±) cis-grandmarin (9) is described as well as the synthesis of some new derivatives in the 5-methoxyseselin series (10-15). The natural coumarins 7-hydroxyalloxanthyletin (6), alloxanthoxyletin (8), and dipetalolactone (7) have also been obtained as secondary products. The type of fusion of the pyrano ring in all cases has been established by 2D NMR spectroscopy. The compounds have been studied for their in vitro antibacterial activity, which has been compared with that of some previously synthesized seselin derivatives. The most active compounds were 3, 7, 8, 11, and 14. Some structure-activity relationships are discussed.

Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3'R,4'R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents

To explore the structural requirements of (+)-cis-khellactone derivatives as novel anti-HIV agents, 24 monosubstituted 3',4'-di-O-(S)- camphanoyl-(+)-cis-khellactone (DCK) derivatives were synthesized asymmetrically. These compounds included 4 isomeric monomethoxy analogues (3- 6), 4 isomeric monomethyl analogues (7-10), 4 4-alkyl/aryl-substituted analogues (11-14), and 12 4-methyl-(+)-cis-khellactone derivatives (15-26) with varying 3',4'-substituents. These (+)-cis-khellactone derivatives were screened against HIV-1 replication in acutely infected H9 lymphocytes. The results demonstrated that the (3'R,4'R)-(+)-cis-khellactone skeleton, two (S)-(-)-camphanoyl groups at the 3'- and 4'-positions, and a methyl group on the coumarin ring, except at the 6-position, were optimal structural moieties for anti-HIV activity. 3-Methyl- (7), 4-methyl- (8), and 5-methyl- (9) 3',4'- di-O-(S)-camphanoyl-(3'R,4'R)-(+)-cis-khellactone showed EC50 and therapeutic index values of -5 μM and >2.15 x 106, respectively, in H9 lymphocytes, which are much better than those of DCK and AZT in the same assay. Furthermore, 8 and 9 also showed potent inhibitory activity against HIV-1 replication in the CEM-SS cell line, and most monosubstituted DCK analogues were less toxic than DCK in both assays.

Anti-AIDS agents - XXVIII. Synthesis and anti-HIV activity of methoxy substitute 3',4'-di-O-(-)-Camphanoyl-(+)-cis-Khellactone (DCK) analogues

Four isomeric methoxy substituted DCK analogues (3-6) were asymmetrically synthesized from different starting materials. 5-Methoxy-3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone (5) exhibited extremely potent anti-HIV activity against HIV-1 replication in H9 lymphocyte cells with EC50 and therapeutic index values of 0.00038 μM and >402,632, respectively, which are better than those of DCK and AZT in this assay.

SYNTHESIS OF NEW PYRANOCOUMARINS

As a result of condensing 5,7-dihydroxy-4-methylcoumarin with dimethyl acetal-3-methylbuten-2-al, 4-methyl-5-hydroxyseseline, 4-methyldipetalolactone and 5-hydroxy-4,10,10-trimethyl-2H,8H-benzodipyran-2-one have been obtained.Condensation of 5,7-hydroxycoumarin with this acetal leads to 5-hydroxyseseline, dipetalolactone and 5-hydroxy-10,10-dimethyl-2H,8H-benzodipyran-2-one

CLAISEN REARRANGEMENTS-XII SYNHESIS OF THE COUMARINS, 5-METHOXYSESELIN, TRACHYPHYLLIN, COUMURRAYIN AND XANTHOXYLETIN

The structure of the natural coumarins, 5-methoxyseselin 7 and trachyphyllin 14 have been confirmed by total syntheses from 7-acetoxy-5-prenyloxycoumarin 1 in good overall yields.Convenient synthetic routes to the natural coumarins, coumurrayin 4 and xanthoxyletin 10 have also been established.