784206-41-3

Basic information

• Product Name: apogossypol
• Synonyms: apogossypol
• CAS NO: 784206-41-3
• Molecular Weight: 462.543
• Mol File: 784206-41-3.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: apogossypol(CAS DataBase Reference)
• NIST Chemistry Reference: apogossypol(784206-41-3)
• EPA Substance Registry System: apogossypol(784206-41-3)

Safety Data

• Hazardous Substances Data: 784206-41-3(Hazardous Substances Data)

Upstream product

• 3117-02-0 2,3-dimethoxy-1,4-benzoquinone 
• 5453-04-3 (±)-gossypol acetic acid 
• 7144-61-8 5,5'-diisopropyl-1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-2,2'-binaphthalene 
• 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 articles and documents

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.

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.

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.