784206-41-3

Upstream product

• 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 
• 73728-76-4 4,4'-dihydroxy-5,5'-diisopropyl-7,7'-dimethyl-bis(3H-naphtho[1,8-bc]furan-3-one) 
• 303-45-7 (rac)-gossypol 

Downstream Products

• 303-45-7 (rac)-gossypol 
• 105201-55-6 acetic acid 1,7,1',6',7'-pentaacetoxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-6-yl ester 
• 1256724-07-8 6,6',7,7'-tetrahydroxy-3,3'-dimethyl-5,5'-bis(4-methylphenethyl)-2,2'-binaphthyl-1,1',4,4'-tetraone 
• 1256724-02-3 N₅,N₅'-bis(4-ethylphenethyl)-6,6',7,7'-tetrahydroxy-3,3'-dimethyl-1,1',4,4'-tetraoxo-1,1',4,4'-tetrahydro-2,2'-binaphthyl-5,5'-dicarboxamide 
• 1256724-01-2 6,6',7,7'-tetrahydroxy-3,3'-dimethyl-N₅,N₅'-bis(3-methylbenzyl)-1,1',4,4'-tetraoxo-1,1',4,4'-tetrahydro-2,2'-binaphthyl-5,5'-dicarboxamide 
• 1256723-98-4 6,6',7,7'-tetrahydroxy-3,3'-dimethyl-1,1',4,4'-tetraoxo-N₅,N₅'-bis(2-phenylpropyl)-1,1',4,4'-tetrahydro-2,2'-binaphthyl-5,5'-dicarboxamide 
• 1256724-20-5 3,3'-dimethyl-5,5'-bis(4-methylphenethyl)-2,2'-binaphthyl-1,1',6,6',7,7'-hexaol 
• 1256724-15-8 1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-5,5'-bis(4-methylphenethyl)-2,2'-binaphthyl 
• 1173895-60-7 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-N₅,N₅'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide 
• 1173895-59-4 N₅,N₅'-bis(4-ethylphenethyl)-1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-2,2'-binaphthyl-5,5'-dicarboxamide 
• 1173895-49-2 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-N₅,N₅'-bis(3-methylbenzyl)-2,2'-binaphthyl-5,5'-dicarboxamide 
• 1173895-39-0 1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N₅,N₅'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide 
• 1173895-37-8 N₅,N₅'-bis(4-ethylphenethyl)-1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-2,2'-binaphthyl-5,5'-dicarboxamide 
• 1173895-24-3 1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N₅,N₅'-bis(3-methylbenzyl)-2,2'-binaphthyl-5,5'-dicarboxamide 

Relevant academic research and scientific papers

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.

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

Synthesis and biological evaluation of apogossypolone derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins

Overexpression of antiapoptotic Bcl-2 family proteins is commonly related with tumor maintenance, progression, and chemoresistance. Inhibition of these antiapoptotic proteins is an attractive approach for cancer therapy. Guided by nuclear magnetic resonan

BI-97C1, an optically pure apogossypol derivative as pan-active inhibitor of antiapoptotic B-cell lymphoma/Leukemia-2 (Bcl-2) family proteins

In our continued attempts to identify novel and effective pan-Bcl-2 antagonists, we have recently reported a series of compound 2 (Apogossypol) derivatives, resulting in the chiral compound 4 (8r). We report here the synthesis and evaluation on its optically pure individual isomers. Compound 11 (BI-97C1), the most potent diastereoisomer of compound 4, inhibits the binding of BH3 peptides to Bcl-XL, Bcl-2, Mcl-1, and Bfl-1 with IC 50 values of 0.31, 0.32, 0.20, and 0.62 μM, respectively. The compound also potently inhibits cell growth of human prostate cancer, lung cancer, and lymphoma cell lines with EC50 values of 0.13, 0.56, and 0.049 μM, respectively, and shows little cytotoxicity against bax -/-bak-/- cells. Compound 11 displays in vivo efficacy in transgenic mice models and also demonstrated superior single-agent antitumor efficacy in a prostate cancer mouse xenograft model. Therefore, compound 11 represents a potential drug lead for the development of novel apoptosis-based therapies against cancer.

Design and synthesis of a gossypol derivative with improved antitumor activities

A novel chemical process has been devised for the synthesis of a new derivative of gossypol, 6,7,6',7'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl- [2,2']binaphthalenyl-1,4,1',4'-tetraone (Apogossypolone). This new process has only four steps, with a shorter synthesis span, a simple purification process, and improved yield and quality. The structure of apogossypolone was characterized by 1H-nuclear magnetic resonance, 13C- nuclear magnetic resonance, mass spectroscopy, infrared spectroscopy, and elemental analysis. Cell-cytotoxicity assay demonstrates that apogossypolone is three- to six-fold more potent than the parent compound, (-)-gossypol, in inhibiting the human prostate tumor cell lines PC-3 and DU-145 as well as the human breast cancer cell line MDA-MB-231. The colony-formation assay with DU-145 cells showed that apogossypolone inhibited more than 70% of colony formation at 1 μM, whereas (-)-gossypol at 10 μM only inhibited less than 50% of colony formation. The results indicate that apogossypolone exerts strong antitumor activities in human prostate and breast cancer cells, and thus represents a promising cancer therapeutic.

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