1178-09-2

Upstream product

• 186581-53-3 diazomethane 
• 138456-91-4 6,7-O,O-demethylene-4'-O-demethylepipodophyllotoxin 
• 518-28-5 podofilox 
• 1174-97-6 6,7-O,O-demethylenepodophyllotoxin 
• 18651-67-7 6,7-O,O-demethylene-6,7-O,O-dimethylpodophyllotoxin 
• 1178-12-7 (3aS,9S,9aS)-6,7-Dimethoxy-9-(3,4,5-trimethoxy-phenyl)-3,3a,9,9a-tetrahydro-naphtho[2,3-c]furan-1,4-dione 
• 1176-70-1 deoxysikkimotoxin 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 104281-87-0 2-<1-hydroxy-1-(3,4,5-trimethoxyphenyl)methyl>-4,5-dimethoxybenzyltrimethylsilane 
• 83392-72-7 (2-bromo-4,5-dimethoxybenzyl)trimethylsilane 
• 104281-91-6 (3aR,4R,9aS)-6,7-Dimethoxy-4-(3,4,5-trimethoxy-phenyl)-3a,4,9,9a-tetrahydro-naphtho[2,3-c]furan-1,3-dione 

Downstream Products

• 138355-94-9 6,7-O,O-demethylene-6,7-O,O-dimethyl-4'-O-demethyl-4β-(4-nitroanilino)-4-desoxypodophyllotoxin 
• 138355-90-5 6,7-O,O-demethylene-6,7-O,O-dimethyl-4β-(4-nitroanilino)-4-desoxypodophyllotoxin 
• 138355-97-2 6,7-O,O-demethylene-6,7-O,O-dimethyl-4'-O-demethyl-4β-(4-fluoroanilino)-4-desoxypodophyllotoxin 
• 138355-93-8 6,7-O,O-demethylene-6,7-O,O-dimethyl-4β-(4-fluoroanilino)-4-desoxypodophyllotoxin 
• 138355-96-1 6,7-O,O-demethylene-6,7-O,O-dimethyl-4'-O-demethyl-4β-(4-cyanoanilino)-4-desoxypodophyllotoxin 
• 138355-92-7 6,7-O,O-demethylene-6,7-O,O-dimethyl-4β-(4-cyanoanilino)-4-desoxypodophyllotoxin 
• 1417534-22-5 C₂₇H₃₂O₉ 
• 1417534-23-6 C₂₉H₃₆O₉ 
• 1417534-24-7 C₃₁H₃₂O₉ 
• 1417534-25-8 C₃₅H₃₄O₉ 
• 1417534-26-9 C₃₀H₂₉NO₁₁ 
• 1180-33-2 DL-Isosikkimotoxinsaeure-methylester 
• 1179-02-8 DL-Isosikkimotoxinsaeure 
• 936333-95-8 C₂₃H₂₇NO₇ 

Relevant academic research and scientific papers

Chemoenzymatic Total Synthesis of Deoxy-, epi-, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones

Podophyllotoxin is probably the most prominent representative of lignan natural products. Deoxy-, epi-, and podophyllotoxin, which are all precursors to frequently used chemotherapeutic agents, were prepared by a stereodivergent biotransformation and a biocatalytic kinetic resolution of the corresponding dibenzylbutyrolactones with the same 2-oxoglutarate-dependent dioxygenase. The reaction can be conducted on 2 g scale, and the enzyme allows tailoring of the initial, “natural” structure and thus transforms various non-natural derivatives. Depending on the substitution pattern, the enzyme performs an oxidative C?C bond formation by C?H activation or hydroxylation at the benzylic position prone to ring closure.

Synthesis and quantitative structure-activity relationship (QSAR) study of novel 4-acyloxypodophyllotoxin derivatives modified in the A and C rings as insecticidal agents

In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, we have synthesized three series of novel 4-acyloxy compounds derived from podophyllotoxin modified in the A and C rings, which is isolated as the main secondary metabolite from the roots and rhizomes of Podophyllum hexandrum. Their insecticidal activity was preliminarily evaluated against the pre-third-instar larvae of Mythimna separata in vivo. Compound 9g displayed the best promising insecticidal activity. It revealed that cleavage of the 6,7-methylenedioxy group of podophyllotoxin will lead to a less active compound and that the C-4 position of podophyllotoxin was the important modification location. A quantitative structure-activity relationship (QSAR) model was developed by genetic algorithm combined with multiple linear regression (GA-MLR). For this model, the squared correlation coefficient (R 2) is 0.914, the leave-one-out cross-validation correlation coefficient (Q2LOO) is 0.881, and the root-mean-square error (RMSE) is 0.024. Five descriptors, BEHm2, Mor14v, Wap, G1v, and RDF020e, are likely to influence the biological activity of these compounds. Among them, two important ones are BEHm2 and Mor14v. This study will pave the way for further design, structural modification, and development of podophyllotoxin derivatives as insecticidal agents.

Synthesis and anti-HIV-1 activities of novel podophyllotoxin derivatives

In order to explore the range of biological activities of the podophyllotoxin compound class, a novel series of derivatives of podophyllotoxin, which were conjugates containing stavudine and different structural podophyllotoxin analogues, were designed, synthesized, and evaluated for their anti-HIV-1 activities in vitro. Among these compounds, 19d and 19c showed the highest anti-HIV-1 activities with EC50 values of 0.17 and 0.29 μM and TI values of 466.9 and 354.5, respectively.

Antitumor agents. 124. New 4β-substituted aniline derivatives of 6,7-O,O- demethylene-4'-O-demethylpodophyllotoxin and related compounds as potent inhibitors of human DNA topoisomerase II

A series of 6,7-O,O-demethylene-4'-O-demethyl-4β-(substituted anilino)-4- desoxypodophyllotoxins (18-23), 6,7-O,O-demethylene-6,7-O,O-dimethyl-4'-O- demethyl-4β-(substituted anilino)-4-desoxypodophyllotoxins (28-31), and their corresponding 4'-O-methyl an

THE TOTAL SYNTHESIS OF (+/-)-SIKKIMOTOXIN VIA THE BENZO-PETERSON REACTION

The total synthesis of a lignan lactone sikkimotoxin (1) in racemic forms has been completed by employing the Benzo-Peterson reaction as key step.