3-Oxo-17,19-ditritoxybeyer-15-en

3-Oxo-17,19-ditritoxybeyer-15-en

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3-Oxo-17,19-ditritoxybeyer-15-en
Category Others
Catalog number BBF-05160
CAS 37589-87-0
Molecular Weight 803.08
Molecular Formula C58H58O3

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Specification

Synonyms 17-Norkaur-15-en-3-one, 18-(triphenylmethoxy)-13-[(triphenylmethoxy)methyl]-, (4α,8β,13β)- (9CI)
IUPAC Name (4aS,5R,6aS,9R,11aS,11bS)-5-hydroxy-4,11b-dimethyl-4,9-bis((trityloxy)methyl)-1,4,4a,5,6,9,10,11,11a,11b-decahydro-6a,9-methanocyclohepta[a]naphthalen-3(2H)-one

Properties

Density 1.19±0.1 g/cm3

Reference Reading

1. Cytotoxic nor-dammarane triterpenes from Viburnum hainanense Merr. et Chun
Wei Wang, Juan Song, GuoBing Shi, QingGong Yu Fitoterapia. 2016 Apr;110:8-12. doi: 10.1016/j.fitote.2016.02.006. Epub 2016 Feb 8.
Five new nor-dammarane triterpenes, 12β-O-acetyl-17β-hydoxy-3,15-dioxo-20,21,22,23,24,25,26,27-octanordammanran (1), 12β-hydoxy-17β-methoxy-3,15-dioxo-20,21,22,23,24,25,26,27-octanordammanran (2), 12β-O-acetyl-3,15-dioxo-17-en-20,21,22,23,24,25,26,27-octanordammanran (3), 12β-hydoxy-15α-O-acetyl-3-oxo-17-en-20,21,22,23,24,25,26,27-octanordammanran (4) and 3β-hydoxy-17-oxo-12-en-20,21,22,23,24,25,26,27-octanordammanran (5), were obtained from the ethanol extract of the whole plants of Viburnum hainanense Merr. et Chun. Structural elucidation of all the compounds was performed by spectral methods such as 1D and 2D NMR, IR, UV, and HRESIMS. The isolated compounds were tested in vitro for cytotoxic potential against seven tumor cell lines (Hep-2, SCL-1, CAL-27, UMSCC-1, Detroit-562, SCC-PKU, and TCA-83). As result, compounds 1 and 2 exhibited cytotoxic activities with IC50 values less than 10 μM.
2. Synthesis of human long-term metabolites of dehydrochloromethyltestosterone and oxymesterone
Nicolas Kratena, Sandra Pfeffer, Valentin S Enev, Günter Gmeiner, Peter Gärtner Steroids. 2020 Dec;164:108716. doi: 10.1016/j.steroids.2020.108716. Epub 2020 Aug 26.
We herein report the synthesis of the long-term metabolites "M4" (IUPAC: 4-chloro-17-hydroxymethyl-17-methyl-18-norandrosta-4,13-dien-3-ol) of dehydrochloromethyl-testosterone (DHCMT, Oral Turinabol) and "Oxy M9" (4-hydroxy-17β-hydroxymethyl-17α-methyl-18-norandrosta-4,13-dien-3-one) of oxymesterone (Oranabol). Both compounds were derived from a common synthetic route starting from dehydroepiandrosterone acetate. Four different stereoisomers were evaluated for metabolite M4. The previously assigned structure could be corrected regarding the C-3 and C-17 stereocenters.
3. Three novel non-nitrogenous cassane diterpenoids from Erythrophleum suaveolens (Guill. et Perr.) Brenan (Fabaceae)
Jacques Dibi Konan, Faustin Aka Kabran, Barthelemy Koffi Attioua, Landry Claude Ahmont Kablan, Sandrine Any-Grah Aka, Armand Angely Koffi, Aminata Ouoyogodé Akoubet, Elvis N'nang Otogo, Blandine Seon-Meniel, Karine Le Blanc, Jean-Christophe Jullian, Drissa Sissouma, Mehdi A Beniddir, Pierre Champy Nat Prod Res. 2021 Apr;35(8):1364-1371. doi: 10.1080/14786419.2019.1650354. Epub 2019 Aug 7.
During our research to contribute to the elucidation of the chemical composition of the root bark of E. suaveolens, six non-nitrogenous cassane diterpenoids (1-6) were isolated and identified. Of these secondary metabolites, three have never been previously described: Cassan-13,15-dien-3-oxo-17-oic acid (2), Cassan-15-en-[7,17]-γ-lactone (3) and 6α-hydroxy-cassamic acid (5). The other are known but, never isolated from the root barks of E. suaveolens (Fabaceae): Cassan-13,15-dien-17-oic acid (1), 6α-hydroxy-cassamic acid methyl esther (4) and cassamic acid (6). Their structures were established according to the spectroscopic data (NMR 1D and 2D, HR-ESI-MS and IR), in comparison with those of literature. The originality of this study lies in the fact that three new natural molecules were isolated and identified. In addition, all the isolated compounds (1-6) were reported for the first time from the root barks of E. suaveolens.

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