59311-29-4

Upstream product

• 56579-86-3 2-(3,4-methylenedioxyphenyl)-1,3-dithiane 
• 497-23-4 2-buten-4-olide 
• 872-85-5 pyridine-4-carbaldehyde 
• 98-01-1 furfural 
• 98-03-3 thiophene-2-carbaldehyde 
• 6527-32-8 4-(benzyloxy)-3,5-dimethoxybenzaldehyde 
• 100-52-7 benzaldehyde 
• 120-57-0 piperonal 

Downstream Products

• 108440-51-3 1-(4-hydroxyphenyl)-3-hydroxymethyl-4-(1,3-dithian)-6,7-methylenedioxy-2-naphtoic acid lactone 
• 108440-52-4 1-(4-hydroxyphenyl)-3-hydroxymethyl-4-keto-1,2,3,4-tetrahydro-6,7-methylenedioxy-2-naphthoic acid lactone 
• 108440-55-7 C₂₄H₂₂O₆S₂ 
• 108440-54-6 2-(4-methoxymethoxybenzyl)-6-keto-5-(1,3-dithian)-3-(3,4-methylenedioxybenzyl)-butyrolactone 
• 108440-56-8 Acetic acid 4-((5S,5aR,8aS)-6,9-dioxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-phenyl ester 
• 108440-56-8 Acetic acid 4-((5S,5aS,8aS)-6,9-dioxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-phenyl ester 
• 108662-73-3 Acetic acid (5S,5aR,8aS,9R)-9-(4-acetoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester 
• 108662-73-3 Acetic acid (5R,5aR,8aS,9R)-9-(4-acetoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester 
• 108662-73-3 Acetic acid (5R,5aR,8aR,9R)-9-(4-acetoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester 
• 119030-78-3 (+/-)-trans-2-benzyl-3-<3,4-(methylenedioxy)benzyl>butyrolactone 

Relevant academic research and scientific papers

Otoe muscade lignan compound and its preparation and use

The invention discloses an otobain compound, a preparation method therefor and application thereof. The compound has a structure shown in formula I. The preparation method is that piperonal is protected by 1,3-propanedithiol, reacts with 2-(5H)-furanone,

Design, synthesis and anticancer activities of novel otobain derivatives

A series of novel racemic otobain derivatives was designed and synthesised using 2-piperonyl-1,3-dithianes in the conjugate addition-alkylation to 5H-furan-2-one, followed by cationic cyclisation. All the synthesised compounds were consequently evaluated for their anticancer activity against several human cancers in vitro. The efficacy of the most active compound 27g was comparable with etoposide, with IC50 values ranging from 1.06 μM to 4.16 μM in different cancer cell lines. Notably, compound 27g strongly induced cell cycle arrest and increased the expression of mitosis-specific markers MPM-2 and phosphorylated histone H3, but it did not trigger cell apoptosis. Further a colony formation assay showed that compound 27g effectively inhibited the anchor growth of lung cancer cells in a dose-dependent manner. More importantly, compound 27g at 40 mg kg-1 significantly suppressed tumour volume (P 0.01) and tumour weight (P 0.05) in a human lung cancer cell xenograft mouse model without causing systematic toxicity in mice. Our findings indicated that compound 27g has significant potential for further drug development.

First total synthesis of justicidone, a p-quinone-lignan derivative from Justicia hyssopifolia

The first synthesis of justicidone (4-(1′,3′-Benzodioxol- 5′-yl)-6-methoxynaphtho[2,3-c]furan-1,5,8(3H)-trione) was carried out from piperonal, as a starting compound, through a lineal process using well known reactions.

Synthesis and cytotoxic activities of analogues of thuriferic acid

Several analogues of thuriferic acid and derivatives, with the 3,4-methylenedioxyphenyl ring replaced by naphthalene, furan, thiophene and carbazole ring systems, have been prepared. The synthetic strategy is based on a conjugate addition-alkylation metho

(-)-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.

Synthesis of heterocyclic analogues of lignans (heterolignans)

A new class of lignan analogues has been synthesized by means of tandem conjugate addition-alkylation of butenolides. Furan and thiophene derivatives have been obtained by this method. This type of compounds has been called heterolignanolides and the generic name heterolignans is proposed for this class of lignan analogues.