634922-45-5

Upstream product

• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 42036-78-2 n-octyltriphenylphosphoniumbromide 
• 124-13-0 Octanal 
• 24131-30-4 (3,5-dimethoxybenzyl)triphenylphosphonium bromide 
• 634922-42-2 1-(3,5-dimethoxyphenyl)nonan-1-ol 

Downstream Products

• 130817-80-0 2-methoxy-6-nonylcyclohexa-2,5-diene-1,4-dione 
• 634922-59-1 2-acetoxy-5-methoxy-3-(non-1-yl)benzo-1,4-quinone 
• 634922-53-5 1,2,4-triacetoxy-5-methoxy-3-(non-1-yl)benzene 
• 59968-08-0 1,3-dimethoxy-5-(non-1-yl)benzene 

Relevant academic research and scientific papers

COMPOUNDS HAVING AGONISTIC EFFECT AGAINST GPR84, PREPARATION METHOD FOR COMPOUNDS AND USE OF COMPOUNDS

The present invention relates to a class of compounds represented by the formula I, or pharmaceutically acceptable salts thereof, methods for their preparation, and application as small molecule tools that function as GPR84 agonists, and their use in preparing a medicament for the treatment of septicemia.

Synthesis and inhibitory activities against colon cancer cell growth and proteasome of alkylresorcinols

We have identified alkylresorcinols (ARs) as the major active components in wheat bran against human colon cancer cell growth (HCT-116 and HT-29) using a bioassay-guided approach. To further study the structure-activity relationships, 15 ARs and their intermediates (1-15) were synthesized expediently by the modified Wittig reaction in aqueous media, and six 5-alkylpyrogallols and their analogues (16-21) were prepared by the general Grignard reaction. The synthetic AR analogues were evaluated for activities against the growth of human colon cancer cells HCT-116 and HT-29 and the chymotrypsin-like activity of the human 20S proteasome. Our results found that (1) AR C13:0 and C15:0 (13 and 14) had the greatest inhibitory effects in human colon cancer cells HCT-116 and HT-29, while decreasing or increasing the side chain lengths diminished the activities; (2) two free meta-hydroxyl groups at C-1 and C-3 on the aromatic ring of the AR analogues greatly contributed to their antitumor activity; (3) the introduction of a third hydroxyl group at C-2 (20 and 21) into the aromatic ring of the AR analogues yielded no significant enhancement in activity against HCT-116 cells and decimated the effects against HT-29 cells, but dramatically increased the activity against the chymotrypsin-like activity of the human 20S proteasome; and (4) AR C11:0 (12) was found to have the greatest effect in a series of AR C9:0-C17:0 against the chymotrypsin-like activity of the human 20S proteasome.

An expedient synthesis of 5-n-alkylresorcinols and novel 5-n-alkylresorcinol haptens

The first synthesis of bioactive long alkyl chain 5-n-alkylresorcinols, present in whole grain products, by a novel modification of the Wittig reaction is described. All the main long chain 5-n-alkylresorcinols present in rye and wheat, including C23 and C25 analogues and haptens, which have not been previously prepared, were synthesised. Microwave-promoted reactions of a semistabilized ylid and alkanals in water gave good yields in both pressurized and open systems. An alternative microwave-promoted synthesis starting from non-stabilized alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the way for the immunochemical detection techniques of alkylresorcinols.

Synthesis and phytotoxicity evaluation of substituted para-benzoquinones

Sorgoleone (1) is one of the major constituents of sorghum root exudates. Sorgoleone is an allelochemical that reduces the growth of broad-leaf plants. The 3,5-dimethoxybenzylic alcohol (3) was used as starting material for the synthesis of 2-methoxy-6-(non-1-yl)benzo-1,4-quinone(9) in 69% yield. Acetylation of (9) with acetic anhydride gave the triacetate (10) in 82% yield. The triacetate (10) was then converted in two steps in 2-hydroxy-5-methoxy-3-(non-1-yl)benzo-1,4-quinone (11) and 2-acetoxy-5-methoxy-3-(non-1-yl)benzo-1,4-quinone (12) in 8% and 37% yield, respectively. Quinone (11) was obtained also by reaction of (12) with DBU in 63% yield. Alkylation of (3) and oxidation with chromic anhydride formed the new quinones (16) (17) and (18) in 23%, 16% and 12% overall yield, respectively. The effect of these quinones and sorgoleone (1) at concentrations of 5.5 μg g-1 on the development of radicle and aerial parts of Cucumis sativus, Brachiaria decumbens, Hyptis lophanta, and Euphorbia heterophylla was tested.