5822-57-1

Usage

Uses

Used in Pharmaceutical Applications:
(3S,5S,10S,13R,14S,17S)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5R)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde is used as a potential pharmaceutical compound for its possible biological activity due to its complex steroidal structure and multiple functional groups.
Used in Medicinal Chemistry Research:
(3S,5S,10S,13R,14S,17S)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5R)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde is used as a subject of study in medicinal chemistry, aiming to explore its potential therapeutic effects and applications in the treatment of various diseases, given its unique structural features and stereochemistry.
Used in Drug Design and Development:
(3S,5S,10S,13R,14S,17S)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5R)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde can be utilized in drug design and development processes, where its structural features may be exploited to create novel therapeutic agents with improved efficacy and selectivity.
Used in Chemical Synthesis:
(3S,5S,10S,13R,14S,17S)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5R)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde may also be used as a starting material or intermediate in the synthesis of other complex organic molecules, particularly those with potential applications in the pharmaceutical or chemical industries.

InChI:InChI=1/C29H42O10/c1-15-22(32)23(33)24(34)25(38-15)39-17-3-8-27(14-30)19-4-7-26(2)18(16-11-21(31)37-13-16)6-10-29(26,36)20(19)5-9-28(27,35)12-17/h11,14-15,17-20,22-25,32-36H,3-10,12-13H2,1-2H3/t15?,17-,18+,19?,20?,22+,23?,24?,25-,26+,27-,28-,29-/m0/s1

Upstream product

• 69980-52-5 2,3,4-tri-O-acetyl-L-rhamnopyranosyl bromide 
• 66-28-4 strophanthidin 
• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 

Downstream Products

• 7044-33-9 convalloside 

Relevant academic research and scientific papers

Antiarol cinnamate and africanoside, a cinnamoyl triterpene and a hydroperoxy-cardenolide from the stem bark of antiaris africana

From the methanol extract of the stem bark of the African tree Antiaris africana Engler, two new bioactive metabolites were isolated, namely, the α-amyrin derivative 1β,11α-dihydroxy-3β-cinnamoyl-α- amyrin (antiarol cinnamate, 1) and a cardiac glycoside, 3β-O-(α-L- rhamnopyranosyl)-14β-hydroperoxy-5β-hydroxy-19-oxo-17β-card- 20(22)-enolide (africanoside, 2a), together with the known compounds-α- amyrin and its acetate, β-sitosterol and its 3-O-β-D-glucopyranoside, friedelin, ursolic and oleanolic acid, 19-norperiplogenin, strophanthidol, strophanthidinic acid, periplogenin (3a), 3-epiperiplogenin, strophanthidin (3b) and 3,3-dimethoxy-4-O-β-D-xylopyronosyl-ellagic acid. Their structures were established on the basis of their spectroscopic data and by chemical methods, while 3a was additionally confirmed by Xray crystal structure analysis. The aglycone moiety possessing a hydroperoxy group was found for the first time in cardenolides. Compounds 1 and 2a showed no activity against bacteria, fungi, and microalgae; however, the crude extract exhibited a high toxicity against Artemia salina and a selective antitumor activity against human tumor cell lines. Africanoside (2a) effected a concentration-dependent inhibition of tumor cell growth with a mean IC50 value of 5.3nM. Georg Thieme Verlag KG Stuttgart - New York.

SYNTHESIS OF CONVALLOSIDE

The known natural diglycoside convalloside - strophanthidin 3β-O- - has been synthesized.The synthesis was carried out by the Koenigs-Knorr method via the preparation as intermediates of convallatoxin and its 2,3-isopropylidene derivative.Selectivity of glycosylation was achieved by the preliminary protection of the two OH groups in the cardenolide L-rhamnoside (convallatoxin).