116515-66-3

Upstream product

• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 103477-58-3 2-(2-bromo-4,5-dimethoxyphenyl)-1,3-dioxolane 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 173197-31-4 1-(3,4-Dimethoxy-phenyl)-4-hydroxy-6,7-dimethoxy-naphthalene-2,3-dicarboxylic acid bis-((S)-1-methoxycarbonyl-ethyl) ester 
• 1402833-96-8 diethyl 1-(3,4-dimethoxyphenyl)-4-hydroxy-6,7-dimethoxynaphthalene-2,3-dicarboxylate 

Relevant academic research and scientific papers

Synthesis and bioevaluation of novel arylnaphthalene lignans as anticancer agents

Novel arylnaphthalene lignans were synthesized and their structures were established by 1H NMR, 13C NMR, and HRMS. These compounds were evaluated for their in vitro cytotoxicity against cancer cell lines by MTT assay. Compound 5d possessed the highest cytotoxicity against KB cells. Apoptosis of KB cells treated with 5d was observed by acridine orange and ethidium bromide double staining assay. Western blot analysis disclosed that 5d induced apoptosis via mitochondrial pathway accompanied by an increased expression of Bax and a decreased expression of Bcl-2.

Hindered rotation in arylnaphthalene lignans

Many arylnaphthalene lignans show biological activity and although few of them contain stereogenic centers, they may nevertheless be chiral if there is hindered rotation about the aryl-naphthalene bond. A relatively high barrier to rotation may give rise to separable rotational enantiomers (atropisomers) which might have quite different pharmacological properties. In order to investigate this possibility we have synthesized the natural products justicidin A, justicidin B, retro-helioxanthin, retro-justicidin B, and helioxanthin as well as four other arylnaphthalenes lignan analogs. We have studied the aryl-naphthalene rotational barrier in these compounds by dynamic NMR and HPLC and find barriers to rotation ranging from 16.9 to 21.5 kcal/mol. This translates to half-lives for individual atropisomers of less than 10 min at room temperature. The experimentally found barriers are compared to those obtained from molecular orbital calculations.

A Novel Synthesis of Naphthalenic Lignan Lactones

Hydroxyphthalans (2) are obtained either through selective reaction of aryllithiums with phthalides (3a,b) or selective reduction of the formyl group in o-formylbenzophenones (7).They are then converted into naphthalenic diesters (5), through isobenzofura