Rocaglaol

Base Information

• Chemical Name: Rocaglaol
• CAS No.: 147059-46-9
• Molecular Formula: C₂₆H₂₆O₆
• Molecular Weight: 434.489
• Mol file: 147059-46-9.mol

Synonyms:8bH-Cyclopenta[b]benzofuran-1,8b-diol,1,2,3,3a-tetrahydro-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-, [1R-(1a,3b,3ab,8bb)]-; Ferrugin; Rocaglaol

Chemical Property of Rocaglaol

Chemical Property:

• PSA: 77.38000
• LogP: 3.73630

Purity/Quality:

98%min ^*data from raw suppliers

Rocaglaol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Rocaglaol is a natural flavagline compound known for its potent anticancer properties, including the ability to inhibit tumor cell proliferation at low nanomolar concentrations while exhibiting minimal toxicity to normal cells. As part of a broader class of plant-derived molecules, it serves as a key structural template for the development of synthetic analogues with enhanced cytotoxicity, such as those modified at specific positions to improve therapeutic efficacy. These findings highlight its potential as a scaffold for novel anticancer agents.

Technology Process of Rocaglaol

There total 10 articles about Rocaglaol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.5%

(±)-(3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one (117828-45-2,136892-17-6,145679-22-7) → 6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydrocyclopentabenzofuran-1,8b(1H)-diol (136850-46-9,136892-16-5,147059-46-9,147202-06-0)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; 1) -78 deg C, 30 min, 2) up to r. t., 3 h;

Reference yield: 93.0%

(±)-(3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one (117828-45-2,136892-17-6,145679-22-7) → (3S,3aR,8bS)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-3-phenyl-1,2,3,3a-tetrahydro-benzo[b]cyclopenta[d]furan-1,8b-diol (136850-46-9,136892-16-5,147059-46-9,147202-06-0)

Guidance literature:

With sodium tetrahydroborate; In methanol; 1) 0 deg C, 6 h, 2) r. t., 2 h;

Reference yield: 50.0%

3-<4,6-dimethoxy-2-(4-methoxyphenyl)-3-oxo-2,3-dihydrobenzofuran-2-yl>-3-phenylpropanal (136850-29-8,136850-45-8) → 6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydrocyclopentabenzofuran-1,8b(1H)-diol (136850-46-9,136892-16-5,147059-46-9,147202-06-0)

Guidance literature:

With samarium diiodide; In methoxybenzene; at 70 ℃; for 0.25h;

DOI:10.1016/S0040-4039(01)01807-X

upstream raw materials:

3-<4,6-dimethoxy-2-(4-methoxyphenyl)-3-oxo-2,3-dihydrobenzofuran-2-yl>-3-phenylpropanal

3-<4,6-dimethoxy-2-(4-methoxyphenyl)-3-oxo-2,3-dihydrobenzofuran-2-yl>-3-phenylpropanal

(±)-(3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one

3-<4,6-dimethoxy-2-(4-methoxyphenyl)-3-oxo-2,3-dihydrobenzofuran-2-yl>-3-phenylpropanal

Downstream raw materials:

(±)-(3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one

(3S,3aR,8bR)-6,8-Dimethoxy-3a-(4-methoxy-phenyl)-8b-methylsulfanylmethoxy-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one

3-<4,6-dimethoxy-2-(4-methoxyphenyl)-3-oxo-2,3-dihydrobenzofuran-2-yl>-3-phenylpropanal

8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-1-oxo-3-phenyl-2,3,3a,8a-tetrahydrocyclopentabenzofuran-2(1H)-carboxamide

Refernces

Novel flavaglines displaying improved cytotoxicity

10.1021/jm101318b

The research investigates the synthesis and cytotoxic properties of novel flavagline analogues with the aim of identifying compounds that could serve as effective anticancer agents. Flavaglines are a class of plant-derived natural products known for their unique anticancer properties, including the ability to inhibit tumor cell proliferation at low nanomolar concentrations without significant toxicity to normal cells. The study explores the structural requirements for cytotoxicity by synthesizing various analogues and examining their effects on different human cancer cell lines. Key chemicals used in the research include rocaglaol (a natural flavagline), FL3 (a synthetic analogue), and various derivatives with modifications at positions C-1, C-2, C-8, and C-40. The researchers found that replacing the hydroxy group at C-1 with an aminoformyl enhanced cytotoxicity and identified compound 18b as particularly effective, reducing tumor growth in a murine allograft model at non-toxic doses. The study concludes that these findings support further preclinical development of flavagline analogues, especially compound 18b, for potential use in cancer treatment.