1045-69-8Relevant articles and documents
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Bellus,D. et al.
, p. 971 - 1009 (1969)
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Improved Method for the Conversion of Enol Lactones to Cyclic α,β-Unsaturated Ketones
Aristoff, Paul A.
, p. 1765 - 1766 (1985)
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Fonken et al.
, p. 5507 (1960)
Design, synthesis and biochemical studies of new 7α-allylandrostanes as aromatase inhibitors
Varela, Carla L.,Amaral, Cristina,Correia-Da-Silva, Georgina,Carvalho, Rui A.,Teixeira, Natércia A.,Costa, Saul C.,Roleira, Fernanda M.F.,Tavares-Da-Silva, Elisiário J.
, p. 662 - 669 (2013)
Two series of derivatives of 7α-allylandrostenedione, namely its 3-deoxo and 1-ene analogs, were designed and synthesised and their biochemical activity towards aromatase evaluated. In each of these series, the C-17 carbonyl group was further replaced by the hydroxyl and acetoxyl groups. The attained data pointed out that the absence of the C-3 carbonyl group led to a slightly decrease in the inhibitory activity and the introduction of an additional double bond in C-1 revealed to be a very beneficial structural change in the studied compounds (compound 12, IC50 = 0.47 μM, Ki = 45.00 nM). Furthermore, the relevance of the C-17 carbonyl group in the D-ring as a structural feature required to achieve maximum aromatase inhibitory activity is also observed for this set of derivatives.
Synthesis and preliminary in vitro biological evaluation of 7α-testosterone-chlorambucil hybrid designed for the treatment of prostate cancer
Bastien, Dominic,Hanna, Rana,Leblanc, Valérie,Asselin, éric,Bérubé, Gervais
, p. 442 - 447 (2013)
The synthesis of 7α-testosterone-chlorambucil hybrid is reported. This compound is made from testosterone in a 6 step reaction sequence and with 23% overall yield. An alternative convergent reaction sequence yielded the same hybrid through a Grubbs metathesis reaction between chlorambucil allyl ester and 7α-allyltestosterone with 35% overall yield. MTT assays showed that the hybrid is selective towards hormone-dependent prostate cancer cell line (LNCaP (AR+)) and shows similar activity than the parent drug, chlorambucil. Thus, the new hybrid shows promising potential for drug targeting of hormone-dependent prostate cancer through its capacity of delivering chlorambucil directly to the site of treatment. This could extend the use of chlorambucil to prostate cancer in the future.
Synthesis and characterization of dimeric steroids based on 5-oxo-4,5-seco-yne units linked by a diyne spacer
Valdez-García, Ricardo M.,Alarcón-Manjarrez, Carlos,Arcos-Ramos, Rafael,Flores-álamo, Marcos,Iglesias-Arteaga, Martín A.
, p. 13 - 22 (2018)
New dimeric steroids in which two 5-oxo-4,5-seco-3-yne steroids units are linked by a flexible diyne spacer, were prepared by both Eglinton and Pd-catalyzed coupling of the corresponding monomers. X-Ray crystallography shows that one of the obtained dimers displays a novel supramolecular network in which the facial hydrophobicity of the steroidal skeleton plays an important role. The crystal packing is dominated by interactions that accommodate the steroid cores in a highly crowded packed columnar self-assembly. Unambiguous NMR characterization of the obtained compounds is also provided.
Aspects of the progesterone response in Hortaea werneckii: Steroid detoxification, protein induction and remodelling of the cell wall
Krizancic Bombek, Lidija,Lapornik, Ajda,Ukmar, Marjeta,Matis, Maja,Cresnar, Bronislava,Katalinic, Jasna Peter,Zakelj-Mavric, Marija
, p. 1465 - 1474 (2008)
Progesterone in sublethal concentrations temporarily inhibits growth of Hortaea werneckii. This study investigates some of the compensatory mechanisms which are activated in the presence of progesterone and are most probably contributing to escape from growth inhibition. These mechanisms lead on the one hand to progesterone biotransformation/detoxification but, on the other, are suggested to increase the resistance of H. werneckii to the steroid. Biotransformation can detoxify progesterone efficiently in the early logarithmic phase, with mostly inducible steroid transforming enzymes, while progesterone biotransformation/detoxification in the late logarithmic and stationary phases of growth is not very efficient. The relative contribution of constitutive steroid transforming enzymes to progesterone biotransformation is increased in these latter phases of growth. In the presence of progesterone, activation of the cell wall integrity pathway is suggested by the overexpression of Pck2 which was detected in the stationary as well as the logarithmic phase of growth of the yeast. Progesterone treated H. werneckii cells were found to be more resistant to cell lysis than mock treated cells, indicating for the first time changes in the yeast cell wall as a result of treatment with progesterone.
Tada,Sawa
, p. 3347,3349 (1968)
HYDROXYLATION OF PROGESTERONE BY CEPHALOSPORIUM APHIDICOLA
Farooq, Afgan,Hanson, James R.,Iqbal, Zahida
, p. 723 - 726 (1994)
The fungus, Cephalosporium aphidicola, has been shown to hydroxylate progesterone predominantly at the 6β- and 11α-positions.Minor metabolites include tetstosterone acetate, the 20(R)-alcohol and 12β,17α-dihydroxyprogesterone.The sequence involves hydroxylation at 11α and then 6β.The hydroxylations of 11α- and 17α-hydroxyprogesterone and 9β,10α-retroprogesterone have also been examined in the light of these results. - Key words: Cephalosporium aphidicola; progesterone; 9β,10α-retroprogesterone; steroid; microbiological hydroxylation.
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Ruzicka,Wettstein
, p. 1264,1273 (1935)
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Highly efficient, solvent-free esterification of testosterone promoted by a recyclable polymer-supported tosylic acid catalyst under microwave irradiation
Borowiecki, Pawe?,Kraszewski, Maciej
, p. 288 - 305 (2019)
Although the classical acylation of testosterone clearly benefits from a broad substrate scope and available catalysts, the requirement of hazardous reagents and the high waste production are its drawbacks. To optimize the process efficiency as well as minimize the environmental impact, we decided to develop a novel method of testosterone esters synthesis, which relies on the usage of recyclable heterogeneous polymer-supported tosylic acid catalyst and microwave-assistance effect in a non-solvent system. Under the established MW-conditions, the acceleration of the process rate was so efficient that the reaction completed within 2.5 min, thus affording the desired esters in the 33–96% yield range without using a work-up procedure. Furthermore, the elaborated catalytic system could be recycled for at least 2 runs not only without a loss of the products yield, but unexpectedly with significant improvement of the reaction efficiency, which may indicate that the reduction of the catalyst loading is possible. We believe that this finding constitutes a very good starting-point for further optimization of the studied process.
Novel catalytic activity of immobilized spores under reduced water activity
Dutta, Tapan K.,Samanta, Timir B.
, p. 629 - 632 (1997)
Onset of a new catalytic function during transformation of progesterone by immobilized spores of Aspergillus ochraceus TS under reduced water activity is reported. The pathway of transformation, which furnished 1,4-androstadien-17β-ol-3-one and 1,4-androstadien-3,17-dione due to cleavage of C17-C20 bond, is different from normal reaction sequence.
Iridium-catalysed highly selective reduction-elimination of steroidal 4-en-3-ones to 3,5-dienes in water
Li, Jide,Tang, Weiping,Ren, Demin,Xu, Jiaxi,Yang, Zhanhui
supporting information, p. 2088 - 2094 (2019/04/29)
Steroidal 3,5-diene is an important structural motif in steroid drugs. In this report, an iridium-catalyzed reduction-elimination of readily available steroidal 4-en-3-ones is realized to prepare steroidal 3,5-dienes. At a low catalyst loading (S/C = 200), heating 4-en-3-ones in a water-mixed organic solvent with formic acid without inert atmosphere protection afforded the desired 3,5-dienes in moderate to excellent yields. In a gram-scale preparation, recrystallization is used instead of column chromatography to purify products. Excellent functionality tolerance and regioselectivity are featured. Structural moieties such as alkanols (primary, secondary and tertiary), esters (except for formate), tolylates, and ketones (endocyclic or exocyclic) are not affected. Surprisingly, the reduction-elimination only takes place at A-ring 4-en-3-ones. In addition, bicyclic 4-en-3-ones are also viable substrates. Synthetic applications of steroidal 3,5-dienes are demonstrated. Our method can also lead to steroidal 3,5-dienes-3-d (>99% d-incorporation) when DCO2D and D2O are used together.
