144405-75-4

Basic information

• Product Name: (2S,3R,5R,10R,13R,14S)-17-Acetyl-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-6-one
• CAS NO: 144405-75-4
• Molecular Weight: 362.466
• Mol File: 144405-75-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (2S,3R,5R,10R,13R,14S)-17-Acetyl-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,5R,10R,13R,14S)-17-Acetyl-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-6-one(144405-75-4)
• EPA Substance Registry System: (2S,3R,5R,10R,13R,14S)-17-Acetyl-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-6-one(144405-75-4)

Safety Data

• Hazardous Substances Data: 144405-75-4(Hazardous Substances Data)

Upstream product

• 76808-40-7 2β,3β,14-tris-(trimethylsilanyloxy)-5β-pregn-7-ene-6,20-dione 
• 123171-35-7 tert-Butyl-[4-((S)-2-methyl-2,3-dihydro-furan-2-yl)-butoxy]-diphenyl-silane 
• 104211-77-0 C₃₂H₄₈O₈ 
• 17086-76-9 cyasterone 
• 84507-67-5 (3aS,5aR,6aR,9aS,10aR,12aR)-3a-Hydroxy-8,8,10a,12a-tetramethyl-1-((1R,2R)-1,2,5-trihydroxy-1,5-dimethyl-hexyl)-1,2,3,3a,5a,6,6a,9a,10,10a,10b,11,12,12a-tetradecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one 
• 5289-74-7 β-ecdysterone 
• 19399-09-8 (3aS,5aR,6aR,9aS,10aR,12aR)-1-Acetyl-3a-hydroxy-8,8,10a,12a-tetramethyl-1,2,3,3a,5a,6,6a,9a,10,10a,10b,11,12,12a-tetradecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one 
• 67-56-1 methanol 
• 5289-74-7 20-Hydroxyecdysone 

Downstream Products

• 5289-74-7 20-Hydroxyecdysone 
• 123171-52-8 (20R,25S)-27(3-(tert-butyl-diphenyl-silanyloxy)-propyl)-2β,3β,14,20,25,5β-pentahydroxycholest-7-ene-6,22-dione 
• 123171-52-8 (20R,25R)-27(3-(tert-butyl-diphenyl-silanyloxy)-propyl)-2β,3β,14,20,25,5β-pentahydroxycholest-7-ene-6,22-dione 

Relevant articles and documents

First example of trifluoromethylation in the ecdysteroid series. Synthesis of (20RS)-20-O-hydro-20-trifluoromethylpoststerone

The title compound was synthesized by trifluoromethylation of poststerone derivatives with trimethyl(trifluoromethyl)silane in the presence of tetrabutylammonium fluoride.

Backstabbing P-gp: Side-chain cleaved ecdysteroid 2,3-dioxolanes hyper-sensitize MDR cancer cells to doxorubicin without efflux inhibition

P-glycoprotein (P-gp, ABCB1) over-expression, causing a multi-drug resistant (MDR) phenotype, is a major problem in cancer chemotherapy that urgently requires novel approaches. Our previous studies showed certain ecdysteroid derivatives as promising chemo-sensitizers against MDR and non-MDR cancer cell lines while also exerting mild to moderate inhibition of P-gp function. Here we report the preparation of a set of substituted 2,3-dioxolane derivatives of poststerone, a known in vivo metabolite of 20-hydroxyecdysone (20E). In contrast with previously studied ecdysteroid dioxolanes, the majority of the new compounds did not inhibit the efflux function of P-gp. Nevertheless, a strong, dose dependent sensitization to doxorubicin was observed on a P-gp transfected cancer cell line and on its susceptible counterpart. We also observed that the MDR cell line was more sensitive to the compounds' effect than the non-MDR. Our results showed for the first time that the chemo-sensitizing activity of ecdysteroids can be fully independent of functional efflux pump inhibition, and suggest these compounds as favorable leads against MDR cancer.

Rapid, laser-induced conversion of 20-hydroxyecdysone-A follow-up study on the products obtained

We have recently reported the set-up of an experimental system for the laser-induced photochemical modification of bioactive substances, where two ecdysteroids, 20-hydroxyecdysone (20E) and its diacetonide derivative served as probes. As a direct continuation of our previous work, three new compounds together with five other ecdysteroid derivatives, have been identified from the novel, laser-induced photo-transformation reaction of 20E. The structures and NMR signal assignment were established by comprehensive one- and two-dimensional NMR spectroscopy supported by mass spectroscopy. Possible ways for the formation of each species is also discussed. Similar to their parental compound, the products obtained are potentially bioactive and worthy for further investigations; due to the low yields, however, a different approach for their higher scale production is suggested.