1778-93-4Relevant articles and documents
Functionalization of testosterone at position 7 and synthesis of 7-(3-methoxypropyl)-4-androsten-17-ol-3-one
Bastien, Dominic,Nault, Josee,Berube, Gervais
, p. 1884 - 1892 (2009)
An efficient transformation of the terminal alkene function of 7-allyltestosterone is reported along with the stereospecific synthesis of 7-(3-methoxypropyl)-4-androsten-17-ol-3-one.
First synthesis of separable isomeric testosterone dimers showing differential activities on prostate cancer cells
Bastien, Dominic,Leblanc, Valérie,Asselin, éric,Bérubé, Gervais
, p. 2078 - 2081 (2010)
The synthesis of two separable isomeric testosterone dimers is reported. The dimers are made from testosterone in a 5 step sequence and with 36% overall yield. The key dimerization step was performed using Hoveyda-Grubb's metathesis catalysts on 7α-allyltestosterone with 75% yield. The synthesis led to separable isomeric dimers (trans and cis, 2:1). X-ray diffraction crystallography, performed on monocrystal of the minor isomer, confirms the cis geometry of the double bound between the two testosterone units. MTT assays showed that the cis dimer has the highest activity against prostate cancer cell lines. The novel cis dimer is more active than the antiandrogen cyproterone acetate indicating the possible therapeutic value of this molecule.
Kinetics of Electrophilic Fluorination of Steroids and Epimerisation of Fluorosteroids
Rozatian, Neshat,Harsanyi, Antal,Murray, Ben J.,Hampton, Alexander S.,Chin, Emily J.,Cook, Alexander S.,Hodgson, David R. W.,Sandford, Graham
supporting information, p. 12027 - 12035 (2020/08/28)
Fluorinated steroids, which are synthesised by electrophilic fluorination, form a significant proportion of marketed pharmaceuticals. To gain quantitative information on fluorination at the 6-position of steroids, kinetics studies were conducted on enol ester derivatives of progesterone, testosterone, cholestenone and hydrocortisone with a series of electrophilic N?F reagents. The stereoselectivities of fluorination reactions of progesterone enol acetate and the kinetic effects of additives, including methanol and water, were investigated. The kinetics of epimerisation of 6β-fluoroprogesterone to the more pharmacologically active 6α-fluoroprogesterone isomer in HCl/acetic acid solutions are detailed.
Microwave induced selective enolization of steroidal ketones and efficient acetylation of sterols in semisolid state
Marwah, Padma,Marwah, Ashok,Lardy, Henry A.
, p. 2273 - 2287 (2007/10/03)
Under microwave irradiation steroidal enones, more specifically, position three carbonyls were efficiently and selectively converted to the corresponding enol acetates in the presence of additional enolizable carbonyl functions at other positions, using acetic anhydride and a catalytic amount of toluene-p-sulfonic acid. Acetylation of hydroxyl groups of the sterols, including those at the hindered positions, was near quantitative. Strictly anhydrous conditions were not a pre-requisite for acetylation and the reaction system easily tolerated up to 10% (v/v) moisture.
Synthesis of C-6 fluoroandrogens: Evaluation of ligands for tumor receptor imaging
Choe, Yearn Seong,Katzenellenbogen, John A.
, p. 414 - 422 (2007/10/02)
Seven androgens, substituted with fluorine at C-6, were prepared as potential imaging agents for androgen receptor-positive prostate tumors and were evaluated in vitro in terms of their lipophilicity and their relative binding affinities (RBA, relative to R1881 = 100) for the androgen receptor and for sex steroid binding protein.Introduction of a fluorine atom into the C-6 position of an androgen generally decreases binding affinity to the androgen receptor, except in the two cases: 6α-fluoro-19-nor-testosterone RBA = 41.6 versus 30.6 for the unsubstituted steroid) and 6α-fluorotestosterone (RBA = 8.9 versus 6.6).Receptor binding of the C-6 fluoro-androgens is also stereospecific, showing higher binding affinities for the α-epimers compared to the corresponding β-epimers (4:1 - 15:1).Binding affinity to sex steroid binding protein is the lowest with 19-nor-testosterone, which is also the least lipophilic androgen studied.Based on the binding properties of compounds in this series, 6α-fluoro-19-nor-testosterone appears to have the most promise as a tumor imaging agent. - Keywords: C-6-fluoroandrogens; fluorine substitution; relative binding affinity; 6α- and 6β-epimers; log Po/w; prostate tumors
Site-Selective Fluorination of Organic Compounds Using 1-Alkyl-4-fluoro-1,4-diazabicyclooctane Salts (Selectfluor Reagents)
Lal, G. Sankar
, p. 2791 - 2796 (2007/10/02)
The new "N-F"-type electrophilic reagent family of 1-alkyl-4-fluoro-1,4-diazabicyclooctane salts (derived from elemental fluorine (F2) and 1-alkyl-1,4-diazabicyclooctane salts) has been found to be very effective for the fluorination of a wide variety of organic substrates.These include steroidal enol acetates and silyl enol ethers, phenyl-substituted olefins, sulfides bearing α-H atoms, certain carbanions, and mildly activated aromatic compounds.The products were obtained with good yields and regioselectivity under very mild reaction conditions.
Stereoscopic synthesis of 4β-deutero-Δ5-3-ketosteroids
Segal,Fradkina,Torgov
, p. 213 - 216 (2007/10/13)
Simple methods for the stereospecific synthesis of 4β-deutero-Δ5-3-ketosteroids have been developed involving the reduction of 3-acetoxy-Δ3, 5-steroids with lithium aluminum hydride and subsequent decomposition with deuterium oxide a
