475-56-9

Usage

Uses

Used in Organic Chemistry:
[2,2'-Binaphthalene]-1,1',6,6',7,7'-hexol, 3,3'-diMethyl-5,5'-bis(1-Methylethyl)is used as a key compound in organic chemistry for its unique molecular structure and potential to form novel chemical entities.
Used in Material Science:
In the field of material science, [2,2'-Binaphthalene]-1,1',6,6',7,7'-hexol, 3,3'-diMethyl-5,5'-bis(1-Methylethyl)is used as a building block for the development of new materials with specific properties, such as optical, electronic, or mechanical characteristics.
Used in Pharmaceutical Research:
[2,2'-Binaphthalene]-1,1',6,6',7,7'-hexol, 3,3'-diMethyl-5,5'-bis(1-Methylethyl)is used as a starting material or intermediate in the synthesis of pharmaceutical compounds, potentially leading to the development of new drugs with improved therapeutic properties.

Upstream product

• 303-45-7 (rac)-gossypol 
• 73728-76-4 4,4'-dihydroxy-5,5'-diisopropyl-7,7'-dimethyl-bis(3H-naphtho[1,8-bc]furan-3-one) 
• 7144-61-8 5,5'-diisopropyl-1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-2,2'-binaphthalene 
• 5453-04-3 (±)-gossypol acetic acid 
• 3117-02-0 2,3-dimethoxy-1,4-benzoquinone 
• 17273-29-9 (+)-Gossypol 

Relevant academic research and scientific papers

A new synthetic route for preparation of enantiomers of gossypol and apogossypol from racemic gossypol

The paper described the preparation of enantiomers of gossypol and apogossypol from racemic gossypol via a two-step procedure. In the first step, D-tryptophan methyl ester was used as an effective agent to resolve racemic gossypol into (–)-gossypol and (+)-gossypol. Next, the deformylation reaction of the corresponding (–)-gossypol and (+)-gossypol was conducted in sodium hydroxide solution, followed by sulfuric acid neutralization in inert atmosphere and the resulting precipitate was filtered and washed with water to give (–)-apogossypol and (+)-apgossypol, respectively in high yields and in high enantiomeric excesses.

Regioselective Bromination and Fluorination of Apogossypol Hexamethyl Ether

Apogossypol hexamethyl ether (3) was brominated upon treatment with any of a number of brominating agents.Each reagent gave a different bromo derivative.Thus, the reaction of 3 with bromine in CCl4 with ultrasound irradiation gave 4 in 71 percent yield.When treated with bromine and iron powder in CCl4 at -5 deg C, 3 afforded 5 in 65 percent yield.The reaction of 3 with pyridinium bromide perbromide in 1,2-dichloroethane at 65-70 deg C furnished 6 in 70 percent yield.Treatment of 3 with NBS in DMF at room temperature afforded 7 in 30 percent yield.Treatment of 4 and 5 with potassium fluoride and 18-crown-6 in acetonitrile at room temperature furnished 8 and 9, respectively.An attempt to introduce trifluoromethyl groups at the 8 and 8' positions of 4, by treatment with cuprous iodide and sodium trifluoroacetate, failed and gave only 10.Interestingly, but unexpectedly, 11 and 12 were produced upon treating 4 with silver(I) fluoride.

Synthesis of 14C-radioactively labeled derivatives of gossypol and the study of their pharmacokinetics

The method of obtaining radioactively labeled 14C-gossypol-acetic add has been improved: from it have been synthesized 14C-derivatives of gossypol and their complexes with N-polyvinylpyrrolidone. A comparative study has been made of the pharmacokinetics of batriden, megosin, and their water-soluble complexes.

Synthesis method of 1, 1 '-deoxygossypol

The invention discloses a systhesiz method of 1, 1 '-deoxygossypol . The method comprises the following steps: 1, taking gossypol acetate I as a starting material, taking gossypol acetate I as a starting material, and removing aldehyde groups to obtain apogossypol II; 2, acetylating the aspogossypol II to obtain aspogossypol III; 3, selectively removing acetyl of the aspogossypol III to obtain an intermediate IV; 4, protecting phenolic hydroxyl of the intermediate IV to obtain an intermediate V; 5, removing acetyl from the intermediate V to obtain an intermediate VI; 6, protecting phenolic hydroxyl of the intermediate VI to obtain an intermediate VII; 7, reducing the protected phenolic hydroxyl group of the VII of the intermediate to obtain a 1, 1'- deoxygossypol precursor VIII; and 8, removing a methoxy group of the 1, 1'- deoxygossypol precursor VIII to obtain a target product 1, 1 '-deoxygossypol . Reaction raw materials are cheap and easy to obtain, synthesis process steps are fewer, the total yield is as high as 45%, reaction conditions are mild, and safety is high. The method is simple in technological process and post-treatment, easy to operate and good in industrial prospect.

Preparation method and intermediate of gossypol and derivative thereof

The invention discloses a preparation method and an intermediate of gossypol and derivatives thereof. The preparation method comprises the following steps: in a solvent, under the action of alkali, apalladium catalyst and a chiral ligand, carrying out a coupling reaction shown in the specification on a compound 6 and a double-boron reagent to obtain a compound (+)-7, wherein the structure of thechiral ligand is shown as a formula L1. The preparation method is simple, easy to operate and suitable for industrial production.

Enantioselective cross-coupling for axially chiral tetra-ortho-substituted biaryls and asymmetric synthesis of gossypol

The axially chiral tetra-ortho-substituted biaryl skeleton exists in numerous biologically important natural products, pharmaceutical molecules, chiral catalysts, and ligands. The efficient synthesis of chiral tetra-ortho-substituted biaryl structures rem

Synthesis and biological evaluation of a novel apogossypolone derivative

Overexpression of antiapoptotic Bcl-2 family proteins plays an important role in tumor maintenance, progression, and chemo-resistance. Targeting these antiapoptotic proteins using nonpeptidic small molecule inhibitors is a new and appealing strategy for cancer therapy. In this study, a novel apogossypolone (ApoG2) derivative, 6, 7, 6′, 7′- tetrahydroxy -3, 3′- dimethyl - [2, 2′] binaphthalenyl-1, 4, 1′, 4′- tetraone (compound 6) was synthesized and screened in vitro for its biological activities. Using the MTT assay and colony formation assay, we found that ApoG2 exerted more potent cytotoxic activities against PC-3 and MDA-231 cells in a dose-dependent manner than the compound 6. In addition, Hoechst 33258 assay results further revealed that ApoG2 exhibits obvious apoptotic characteristics in a dose-dependent manner, but the compound 6 led to apoptosis with less extent. Taken together, albeit the compound 6 inferior to ApoG2 in many ways on cancer cells in vitro, our results suggest that the compound 6 still represents a candidate drug for the development of novel apoptosis-based therapies for cancer.

Gossypol derivatives and preparation thereof, application of gossypol derivatives in pesticide and anti-cancer activity

The invention relates to gossypol derivatives and preparation method thereof and application of the gossypol derivatives in plant virus prevention and control, insecticidal action, bactericidal action and anti-cancer action, wherein the significance of all groups in a formula is shown in the description. The gossypol derivatives show the excellent anti-plant virus activity, bactericidal activity, insecticidal activity and anti-cancer activity.

Inhibitory effects of gossypol, gossypolone, and apogossypolone on a collection of economically important filamentous fungi

Racemic gossypol and its related derivatives gossypolone and apogossypolone demonstrated significant growth inhibition against a diverse collection of filamentous fungi that included Aspergillus flavus, Aspergillus parasiticus, Aspergillus alliaceus, Aspergillus fumigatus, Fusarium graminearum, Fusarium moniliforme, Penicillium chrysogenum, Penicillium corylophilum, and Stachybotrys atra. The compounds were tested in a Czapek agar medium at a concentration of 100 μg/mL. Racemic gossypol and apogossypolone inhibited growth by up to 95%, whereas gossypolone effected 100% growth inhibition in all fungal isolates tested except A. flavus. Growth inhibition was variable during the observed time period for all tested fungi capable of growth in these treatment conditions. Gossypolone demonstrated significant aflatoxin biosynthesis inhibition in A. flavus AF13 (B1, 76% inhibition). Apogossypolone was the most potent aflatoxin inhibitor, showing greater than 90% inhibition against A. flavus and greater than 65% inhibition against A. parasiticus (B1, 67%; G 1, 68%). Gossypol was an ineffectual inhibitor of aflatoxin biosynthesis in both A. flavus and A. parasiticus. Both gossypol and apogossypolone demonstrated significant inhibition of ochratoxin A production (47%; 91%, respectively) in cultures of A. alliaceus.

NAPHTHALENE-BASED INHIBITORS OF ANTI-APOPTOTIC PROTEINS

Methods of using apogossypol and its derivatives for treating inflammation is disclosed. Also, there is described a group of compounds having structure A, or a pharmaceutically acceptable salt, hydrate, N-oxide, or solvate thereof are provided: wherein ea