73354-08-2

Upstream product

• 580-72-3 (2RS,3RS)-2,3-bis-(4-hydroxy-3-methoxybenzyl)butyrolactone 
• 67-68-5 dimethyl sulfoxide 
• 26687-82-1 Arctigenin 

Downstream Products

• 119069-38-4 (3R,4R)-3-(3,4-dimethoxybenzyl)-4-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran 
• 119030-69-2 (8R,8'R)-4'-benzyloxy-3,3',4-trimethoxylignan-9,9'-diol 
• 119030-70-5 (8R,8'R)-4'-benzyloxy-3,3',4-trimethoxylignan-9,9'-diyl diacetate 
• 73354-11-7 (8R,8'R)-4'-hydroxy-3,3',4-trimethoxylignan-9,9'-diyl diacetate 
• 58311-18-5 (2R,3R)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butane-1,4-diol 
• 119030-71-6 Acetic acid (2R,3R)-2-(3,4-dimethoxy-benzyl)-4-(4-hydroxy-3-methoxy-phenyl)-3-hydroxymethyl-butyl ester 
• 119030-72-7 Acetic acid (2R,3R)-4-(3,4-dimethoxy-phenyl)-2-(4-hydroxy-3-methoxy-benzyl)-3-hydroxymethyl-butyl ester 

Relevant academic research and scientific papers

Synthesis and pharmacological characterisation of arctigenin analogues as antagonists of AMPA and kainate receptors

(-)-Arctigenin and a series of new analogues have been synthesised and then tested for their potential as AMPA and kainate receptor antagonists of human homomeric GluA1 and GluK2 receptors expressed in HEK293 cells using a Ca2+ influx assay. In general, these compounds showed antagonist activity at both receptors with greater activity evident at AMPARs. Schild analysis indicates that a spirocyclic analogue 6c acts as a non-competitive antagonist. Molecular docking studies in which 6c was docked into the X-ray crystal structure of the GluA2 tetramer suggest that (-)-arctigenin and its analogues bind in the transmembrane domain in a similar manner to the known AMPA receptor non-competitive antagonists GYKI53655 and the antiepileptic drug perampanel. The arctigenin derivatives described herein may serve as novel leads for the development of drugs for the treatment of epilepsy. This journal is

(-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase

The natural dibenzylbutyrolactone type lignanelide (-)-arctigenin (2), an inhibitor of human irnmunodeficiency virus type-1 (HIV-1) replication in infected human cell systems, was found to suppress the integration of proviral DNA into the cellular DNA genome. In the present study 2 was tested with purified HIV-1 integrase and found to be inactive in the cleavage (3'- processing) and integration (strand transfer) assays. However, the semisynthetic 3-O-demethylated congener 9 characterized by a catechol substructure exhibited remarkable activities in both assays. Structure- activity relationship studies with 30 natural (1-6), semisynthetic (7-21), and synthetic (37-43, 45, 46) lignans revealed that (1) the lactone moiety is crucial since compounds with a butane-1,4-diol or tetrahydrofuran substructure and also lignanamide analogues lacked activity and (2) the number and arrangement of phenolic hydroxyl groups is important for the activity of lignanolides. The congener with two catechol substructures (7) was found to be the most active compound in this study. 7 was also a potent inhibitor of the 'disintegration' reaction which models the reversal of the strand transfer reaction. The inhibitory activity of 7 with the core enzyme fragment consisting of amino acids 50-212 suggests that the binding site of 7 resides in the catalytic domain.

Studies on differentiation inducers. VI. Lignan derivatives from arctium fructus. (2)

In the previous paper, we reported the differentiation inducing activities of lignoids from Arctium Fructus (the fruits of Arctium lappa L., Compositae) against mouse myeloid leukemia cells (M1). We reinvestigated the active components of this extract and isolated three new dilignans. Furthermore, structure modifications were carried out using the most active lignan (arctigenin, 1) and its structure activity relationship was investigated. Its aliphatic esters were more effective in inducing the differentiation of M1 cells than its aromatic esters. Especially, n- decanoate, which was the most active derivative, induced more than half of the M1 cells into phagocytic cells at a concentration of 2 μM.

Oxidative Coupling of Lignans. IV. Monophenolic Oxidative Coupling

Oxidative coupling of the monophenolic monoester (6) gives an aryltetralin (12) which is a potential intermediate for the synthesis of clinically active monophenolic lignan lactones.In contrast, oxidative couplings of the monophenols (32) and (35), derived from matairesinol (29), give mixtures of diastereoisomeric cyclooctadiene lignans while 4'-demethyldeoxypodorhizon (26) does not cyclize.These results show that the degree of aromatic substitution in monophenolic diarylbutanes plays an important role in determining the outcome of oxidative coupling.An alternative synthesis of the lactone (57) from piperonal has been investigated.