697235-39-5

Basic information

• Product Name: Episilvestrol
• Synonyms: Episilvestrol;(1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1S)-1,2-Dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxylic acid methyl ester
• CAS NO: 697235-39-5
• Molecular Formula: C₃₄H₃₈O₁₃
• Molecular Weight: 654.65772
• Mol File: 697235-39-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Episilvestrol(CAS DataBase Reference)
• NIST Chemistry Reference: Episilvestrol(697235-39-5)
• EPA Substance Registry System: Episilvestrol(697235-39-5)

Safety Data

• Hazardous Substances Data: 697235-39-5(Hazardous Substances Data)

Usage

Definition

ChEBI: An organic heterotricyclic compound that is a 5'''-epimer of silvestrol. Isolated from Aglaia silvestris, it exhibits antineoplastic activity.

Upstream product

• 960505-99-1 C₄₆H₆₆O₁₃Si₂ 

Downstream Products

• 1426430-11-6 C₅₆H₇₅N₇O₁₇S 
• 1426430-10-5 C₃₆H₃₉NO₁₂ 
• 1426430-09-2 C₃₄H₃₉NO₁₂ 
• 1426430-08-1 episilvesteric acid 
• 697235-38-4 (1R,2R,3S,3aR,8bS)-methyl 6-(((2S,3R,6R)-6-((R)-1,2-dihydroxyethyl)-3-methoxy-1,4-dioxan-2-yl)oxy)-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxylate 

Relevant articles and documents

Total synthesis of the potent anticancer Aglaia metabolites (-)-silvestrol and (-)-episilvestrol and the active analogue (-)-4-desmethoxyepisilvestrol

Total synthesis of the anticancer 1,4-dioxane containing natural products silvestrol (1) and episilvestrol (2) is described by an approach basedon the proposed biosynthesis of these novel compounds. The key steps in cluded an oxidative rearrangement of the protected D-glucose derivative 11 to afford the 1,4-dioxane 12, which could be elaborated to the coupling partner 5 and a photochemical [3 + 2] cycloadditon between the 3-hydroxyflavone 27 and methyl cinnamate followed by base-induced α-ketol rearrangement and reduction to give the cyclopentabenzofuran core 33. The core (-)-6 and 1,4-dioxane fragment 5 were united by a highly stereoselective Mitsunobu coupling with the modified azodicarboxylate DMEAD toafford the axial coupled product 36. Deprotection then gave episilvestr ol (2). Silvestrol (1) was synthesized by a coupling between core (-)-6 and the dioxane 44 followed by deprotection. Compound 1 was also synthesized from episilvestrol (2) by a Mitsunobu inversion. In addition, the analogue 4-desmethoxyepisilvestrol (46) was synthesized via the same route. It was found that 46 and episilvestrol 2 displayed an unexpected concentration-dependent chemical shift variation for the nonexchangeable dioxane protons. Synthetic compounds 1, 2, 38, 46, and 54 were tested against cancer cells lines, and it was found that the stereochemistry of the core was critical for activity. Synthetic analogue 4-desmethoxyepisilvestrol (46) was also active against lung and colon cancer cell lines.

PROCESSES AND INTERMEDIATES

The present invention relates to synthetic processes for the preparation of compounds bearing a dioxanyl moiety, in particular to compounds bearing a dioxanyl side chain attached to a mono- or polycyclic core moiety, more particularly a cyclopentabenzofuran core moiety. The invention also relates to intermediate compounds used in these processes. Compounds which can be prepared by the process of the invention can be used as candidates for screening for potential therapeutic activity, thus the invention also relates to compounds obtainable or prepared by the methods described above, in particular to those having cytotoxic or cytostatic activity.