33766-62-0

Upstream product

• 143-62-4 (+)-digitoxigenin 
• 83911-60-8 5-(3'β-benzyloxy-14'-hydroxy-5'β,14'β-androstan-17'β-yl)-2H-pyran-2-one 
• 773-64-8 2-mesitylenesulphonyl chloride 
• 83911-57-3 5-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-3,6-dihydro-2H-pyran-2,3-diol 
• 83911-59-5 5-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-2H-pyran-2-one 
• 83911-58-4 5-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-3-hydroxy-3,6-dihydro-2H-pyran-2-one 
• 83911-56-2 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)2,5-dihydroxy-3-pentanal ethylene acetal 
• 83911-55-1 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)furan-2-carbaldehyde ethylene acetal 
• 64647-72-9 3β-t-butyldimethylsilyloxy-5β-androst-15-ene-17one 
• 571-31-3 Epietiocholanolone 
• 1229-12-5 androstane-3,17-dione 
• 63-05-8 Androstenedione 

Downstream Products

• 4029-66-7 (3β,5β)-3-(acetyloxy)-14-hydroxy-bufa-20,22-dienolide 
• 118661-50-0 14-hydroxy-3β-(4-nitro-benzoyloxy)-5β,14β-bufa-20,22-dienolide 
• 18126-17-5 3β-hydroxy-21-nor-5β-pregnen-(14)-oic acid-(20) 
• 3714-45-2 12β-hydroxybufalin 
• 60617-83-6 bufalin 3-succinate 
• 113960-56-8 bufalin 3-[N-(tert-butoxycarbonyl)hydrazido]succinate 
• 852831-45-9 12α-hydroxybufalin 
• 852831-46-0 7β,12α-dihydroxybufalin 
• 852831-47-1 7β,15α-dihydroxybufalin 
• 852831-48-2 5β,7β-dihydroxybufalin 
• 1314863-61-0 4-nitrophenyl carbamate-3-O-bufalin 
• 1314863-48-3 (3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl(2-(pyrrolidin-1-yl)ethyl)carbonate 
• 1314863-49-4 4-(((((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)carbonyl)amino)butanoic acid 
• 1314863-50-7 (3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl(2-(pyrrolidin-1-yl)ethyl)carbamate 

Relevant academic research and scientific papers

New cytotoxic bufadienolides from the roots and rhizomes of Helleborus thibetanus Franch

Three new bufadienolides 14β, 16β-dihydroxy-3β-[β-D-glucopyranosyl-(1→6)-(β-D-glucopyranosyl)oxy]-5α-bufa-20, 22-dienolide (1), 14β-hydroxy-3β-[β-D-glucopyranosyl-(1→4)-(β-D-glucopyranosyl)oxy]-5α-bufa-20, 22-dienolide (2) and hellebrigenin-3-O-β-D-glucosyl-(1→4)-β-D-glucoside (3), together with eight known bufadienolides (4–11) were isolated from the roots and rhizomes of Helleborus thibetanus. Their structures were elucidated by extensive spectroscopic methods and acid hydrolysis. Compounds 1–7 were evaluated for their cytotoxic activity against HCT116, A549 and HepG2 tumor cell lines. Compound 1 exhibited moderate cytotoxicity against HepG2 cells with IC50 value of 15.1 ± 1.72 μM. Compounds 5 and 6 exhibited moderate cytotoxicity against HCT116 cells with IC50 values of 15.12 ± 0.58 μM and 13.17 ± 2.34 μM, respectively.

Unified Total Synthesis of Five Bufadienolides

We report a unified total synthesis of five bufadienolides: bufalin (1), bufogenin B (2), bufotalin (3), vulgarobufotoxin (4), and 3-(N-succinyl argininyl) bufotalin (5). After the steroidal ABCD ring 8 was produced, the D ring was cross-coupled with a 2-pyrone moiety and stereoselectively epoxidized to generate 6. TMSOTf promoted a stereospecific 1,2-hydride shift from 6 to establish the β-oriented 2-pyrone of 19. Functional group manipulations from 19 furnished 1-5, which potently inhibited cancer cell growth.