697235-38-4

Usage

Uses

Used in Antineoplastic Applications:
(1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-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 is used as an antineoplastic agent, specifically for its potential to inhibit the growth and proliferation of cancer cells. Its antineoplastic activity makes it a promising candidate for the development of novel cancer therapies.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-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 is used as a key compound in the development of new drugs targeting cancer treatment. Its unique structure and antineoplastic properties offer opportunities for the creation of innovative therapeutic agents.
Used in Research and Development:
(1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-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 is utilized in research and development for understanding its mechanism of action, potential side effects, and optimization for therapeutic use. (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-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 serves as a valuable tool for scientists to explore new avenues in cancer research and drug development.

Anticancer Research

It is a natural flavogline compound from the group of cyclopenta[b]benzofurans,extracted from the fruits of Aglaila sylvestre, which shows anticancer activityagainst lung and breast cancers (Shoeb 2006). The plant extract is reported to bepotent against P-388 cells in in vivo experiments. In the hollow fiber in vivo assay,it shows cytotoxicity in a dose-dependent way. It works by altering the cell signal pathways that related to the cell survival as well as angiogenesis and exerts itseffects by inhibiting the translation of mRNA preferentially associated withmalignancy (Balunas and Kinghorn 2005; Cencic et al. 2009).

Upstream product

• 62-23-7 4-nitro-benzoic acid 
• 697235-39-5 5'''-episilvestrol 
• 960365-65-5 (1R,2R,3S,3aR,8bS)-methyl 1,6,8b-trihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate 
• 960365-79-1 C₄₈H₅₀O₁₃ 

Relevant academic research and scientific papers

SILVESTROL ANTIBODY-DRUG CONJUGATES AND METHODS OF USE

The invention relates generally to a silvestrol molecule activated with a leaving group. The invention further relates generally to an antibody-drug conjugate comprising an antibody conjugated by a linker to one or more silvestrol drug moieties and methods of treatment.

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.

Enantioselective synthesis of the complex rocaglate (-)-silvestrol

The total synthesis of the natural product (-)-silvestrol (1) has been accomplished and features enantioselective [3+2] photocycloaddition of a substituted 3-hydroxyflavone and methyl cinnamate promoted by a chiral Bronsted acid. Initial biological studies indicate a 5-10-fold greater activity of silvestrol as an inhibitor of protein synthesis in HeLa cells than its 1″″ diastereomer.

Total synthesis of (-)-episilvestrol and (-)-silvestrol

Sugar and spice... The total synthesis of the rare but potent anticancer natural product (-)-episilvestrol and its 5? epimer (-)-silvestrol was accompushed from D-glucose, naringenin, and methyl cinnamate (see scheme). The key steps of the sequence were inspired by the possible biogenesis of these compounds.

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.