2530-07-6

Usage

Uses

Used in Pharmaceutical Industry:
Tigogenin acetate is used as a key intermediate for the synthesis of various semi-synthetic steroids and steroidal drugs for the treatment of conditions such as inflammation, allergies, and various hormonal imbalances.
Used in Drug Development:
Tigogenin acetate is used as a starting material in the development of new drugs for the treatment of various medical conditions, due to its unique chemical structure and properties.

InChI:InChI=1/C29H46O4/c1-17-8-13-29(31-16-17)18(2)26-25(33-29)15-24-22-7-6-20-14-21(32-19(3)30)9-11-27(20,4)23(22)10-12-28(24,26)5/h17-18,20-26H,6-16H2,1-5H3/t17-,18+,20+,21+,22-,23+,24+,25+,26+,27+,28+,29-/m1/s1

Upstream product

• 77-60-1 tigogenin 
• 108-24-7 acetic anhydride 
• 24742-79-8 (25R)-3β-Acetoxy-5α-spirostan-15-on 
• 117019-62-2 (25R)-3β-hydroxy-5α14β-spirostan-11-one 
• 77-60-1 3-epismilagenin 
• 126-19-2 sarsasapogenin 
• 88908-42-3 C₂₉H₄₇IO₄ 
• 88908-42-3 C₂₉H₄₇IO₄ 
• 39636-34-5 dihydrotigogenin 3-acetate 
• 39636-34-5 Acetic acid (4aS,4bS,6aS,7S,8R,10aS,10bR,12aS)-8-(4-hydroxy-3-methyl-butyl)-4a,6a,7-trimethyl-octadecahydro-9-oxa-pentaleno[2,1-a]phenanthren-2-yl ester 
• 77-60-1 tigogenin 
• 74808-10-9 2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate 
• 92052-38-5 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloracetimidate 
• 838087-02-8 (25S)-5β-furost-20(22)-ene-3β,26-diyl diacetate 

Downstream Products

• 1236306-01-6 (23R,25R)-23-phenylseleno-5α-spirostan-3β-ol acetate 
• 140195-62-6 (23R,25R)-3β-acetoxy-16α,23:23,26-diepoxy-5α-cholestan-22-one 
• 28404-65-1 23-oxo-tigogenin acetate 
• 469-00-1 sarsasapogeninoic acid 
• 16787-53-4 (25S)-3β-hydroxy-5β-spirostan-23-one 
• 914477-77-3 (23R,25S)-3β-acetoxy-16β,23:23,26-diepoxy-5β-cholestan-22-one 
• 1236306-02-7 (23R,25S)-23-phenylseleno-5β-spirostan-3β-ol acetate 
• 35319-92-7 (25S)-3β-acetoxy-5β-spirostan-23-one 
• 1380412-89-4 [23(23')E, 25S]-23(23')-benzylidene-5β-spirostan-3β-ol acetate 
• 359416-36-7 3β-acetoxy-16β-hydroxy-5β-bisnorcholanoic acid 22->16 lactone 
• 511-92-2 (25S)-5β-Spirostan 
• 126-19-2 sarsasapogenin 
• 289042-56-4 3-O-p-bromobenzoylsarsasapogenin 
• 1380412-87-2 [23(23')E,25R]-23(23')-benzylidene-5α-spirostan-3β-ol acetate 

Relevant academic research and scientific papers

Synthesis of clionamine B, an autophagy stimulating aminosteroid isolated from the sponge Cliona celata

Clionamine B (2), an aminosteroid isolated from the marine sponge Cliona celata, has been synthesized starting from the plant sapogenin tigogenin (5). A key step in the synsthesis is the stereoselective introduction of the C-20 α-hydroxyl substituent via oxidation of a γ-lactone enolate with molecular oxygen. Synthetic clionamine B (2) strongly stimulated autophagy in human breast cancer MCF-7 cells.

Concise large-scale synthesis of tomatidine, a potent antibiotic natural product

Tomatidine has recently generated a lot of interest amongst the pharmacology, medicine, and biology fields of study, especially for its newfound activity as an antibiotic agent capable of targeting multiple strains of bacteria. In the light of its low natural abundance and high cost, an efficient and scalable multi-gram synthesis of tomatidine has been developed. This synthesis uses a Suzuki–Miyaura-type coupling reaction as a key step to graft an enantiopure F-ring side chain to the steroidal scaffold of the natural product, which was accessible from low-cost and commercially available diosgenin. A Lewis acid-mediated spiroketal opening followed by an azide substitution and reduction sequence is employed to generate the spiroaminoketal motif of the natural product. Overall, this synthesis produced 5.2 g in a single pass in 15 total steps and 15.2% yield using a methodology that is atom economical, scalable, and requires no flash chromatography purifications.

Sarsasapogenin-structure-modified derivatives, pharmaceutical compositions thereof and applications of the compositions

The invention relates to sarsasapogenin-structure-modified derivatives. The derivatives are characterized in that the structure formulas of the derivatives are shown as (I) and (II); pharmaceutical compositions of the derivatives and applications thereof are also provided; and many of the newly synthesized compounds show activity superior to activity of lead compounds through activity testing aiming at AD related targets. The compositions have high practical value for treating senile dementia. Defects of sarsasapogenin-structure-modified derivatives in the prior art are made up. The derivatives and the compositions are of great significance.

Epimerization of C-22 in (25R)- and (25S)-sapogenins

Most of the naturally occurring steroidal sapogenins (C-23 non-substituted frameworks), possess an R configuration at the spiro C-22 center. Their C-22 epimers have become important targets in biological research. This paper describes a procedure to obtain 22S-spirostans from 22R-sapogenins and pseudosapogenin skeletons, without affecting the chirality at either C-25 or C-20. An optimal way to synthesize the pair of C-22 stereoisomers of 23-acetyldiosgenin is also reported. The latter was obtained from a 22,26-epoxycholestane or from 23-acetylfurostene compounds.

Epimerization of C-22 in (25R)- and (25S)-sapogenins

Most of the naturally occurring steroidal sapogenins (C-23 non-substituted frameworks), possess an R configuration at the spiro C-22 center. Their C-22 epimers have become important targets in biological research. This paper describes a procedure to obtain 22S-spirostans from 22R-sapogenins and pseudosapogenin skeletons, without affecting the chirality at either C-25 or C-20. An optimal way to synthesize the pair of C-22 stereoisomers of 23-acetyldiosgenin is also reported. The latter was obtained from a 22,26-epoxycholestane or from 23-acetylfurostene compounds.

The crystal structure of 3-epismilagenin acetate and 23-oxo-3-epismilagenin acetate

The crystal structure together with unambiguous assignation of 1H and 13C NMR signals of 3-epismilagenin acetate 4 and 23-oxo-3-epismilagenin acetate 5 are described. Compound 4, crystallized as orthorhombic system a = 10.535(1) A, b = 13.775 (1) A, c = 18.347 (1) A, α = β = γ = 90°; with space group P2 1 2 1 2 1 ; while compound 5 crystallized as a monoclinic system a = 10.380(1) A, b = 7.327(1) A, c = 17.881(1) A, α = γ = 90°, β = 99.56(1)°, with a space group P2 1 . The presence a carbonyl group at C(23) in compound 5 produces a significant deviation from the chair conformation observed in compound 4. The effects of the side chain modifications on the puckering parameters derived from are discussed.

Synthesis of 5(6)-dihydro-OSW-1 by using the intact skeleton of tigogenin

5(6)-Dihydro-OSW-1 (1), an analogue of OSW-1 with the potent anticancer activity, was synthesized by utilizing the intact skeleton of tigogenin in 13 steps in 9.0% overall yield. This synthesis demonstrated an effective and reasonable synthetic strategy for bioactive steroids with side chains as compared with their routine synthesis.

Cyanoglycosylation accompanied by ring-opening of spirostanols

The reaction of 3-O-acetylsarsasapogenin (7), which has no hydroxyl group susceptible to glycosylation, with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (5) in the presence of a mixed catalyst, Hg(CN)2 and HgBr2, caused by clea

TRANSFORMATIONS OF SOLASODINE AND DERIVATIVES OF HECOGENIN BY CUNNINGHAMELLA ELEGANS

Incubation of (25R)-5α-spirostane-3β,12β-diol (rickogenin) with the fungus Cunninghamella elegans led to the formation of (25R)-7β,12β-dihydroxy-5α-spirostan-3-one, (25R)-5α-spirostan-3β,7β,12β-triol and (25R)-5α-spirostan-3β,7α,12α-triol.Incubation of (25R)-5α-spirostan-3,12-dione (hecogenone) with the same fungus gave rise to (25R)-5α-spirostan-3,7,12-trione.When the (22R,25R)-spirosolane, solasod-5-en-3β-ol (solasodine) was incubated with C. elegans, solasod-5-ene-3β,7β-diol, solasod-5-ene-3β,7α-diol and 3β-hydroxysolasod-5-en-7-one were produced.In contrast, incubation of solasodine with Penicillium patulum gave solasod-4-en-3-one and the 6-methylsalicylic acid salt of solasodine.