- A New Synthesis of 19-Nor Steroids via 2,4-Dibromoestrogens
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19-Nor steroids (7) and (8) have been synthesised via oxidation of 2,4-dibromoestrogens (1) and (2) with nitric acid followed by hydrogenation over palladium-on-charcoal and subsequent treatment with Nafion-H.
- Numazawa, Mitsuteru,Hoshi, Kumiko,Kimura, Katsuhiko
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- Microbial transformation of nandrolone decanoate by acremonium strictum
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Estr-4-en-3,17-dione II, 17β-hydroxyestr-4-en-3-one III, 15α-hydroxyestr-4-en-3,17-dione IV, and 15α,17β-dihydroxyestr- 4-en-3-one V were produced by microbial transformation of nandrolone decanoate I in the culture of Acremonium strictum PTCC 5282. Bioconversion characteristics observed were ester hydrolysis, oxidation, and hydroxylation. Each microbial product was purified chromatographically and characterized on the basis of spectral data obtained from 1H-NMR, 13C-NMR, FT-IR, MS, and physical constants such as melting point and optical rotation.
- Yazdi, Mojtaba Tabatabaei,Zanjanian, Seyedeh Maryam,Faramarzi, Mohammad Ali,Amini, Mohsen,Amani, Amir,Abdi, Khosrou
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- Where does hydrolysis of nandrolone decanoate occur in the human body after release from an oil depot?
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Long-term therapy of nandrolone (N) is recommended to increase mineral density and muscle strength. Using a parenteral sustained release drug formulation with nandrolone decanoate (ND), therapeutic N levels can be achieved and maintained. Until now, it is unknown if hydrolysis of ND into N occurs in tissue at the injection site or after systemic absorption. Therefore, hydrolysis studies were conducted to investigate the location and rate of ND hydrolysis after its release from the oil depot. ND hydrolysis was studied in porcine tissues, to mimic the human muscular and subcutaneous tissues. Additionally, the ND hydrolysis was studied in human whole blood, plasma and serum at a concentration range of 23.3–233.3?μM. ND hydrolysis only occurred in human whole blood. The hydrolysis did not start immediately, but after a lag time. The mean lag time for all studied concentrations was 34.9?±?2.5?min. Because of a slow penetration into tissue, hydrolysis of ND is found to be very low in surrounding tissue. Therefore the local generation of the active compound is clinically irrelevant. It is argued that after injection of the oil depot, ND molecules will be transported via the lymphatic system towards lymph nodes. From here, it will enter the central circulation and within half an hour it will hydrolyse to the active N compound.
- Kalicharan,Bout,Oussoren,Vromans
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- Extreme electric fields power catalysis in the active site of ketosteroid isomerase
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Enzymes use protein architecture to impose specific electrostatic fields onto their bound substrates, but the magnitude and catalytic effect of these electric fields have proven difficult to quantify with standard experimental approaches. Using vibrational Stark effect spectroscopy, we found that the active site of the enzyme ketosteroid isomerase (KSI) exerts an extremely large electric field onto the C=O chemical bond that undergoes a charge rearrangement in KSI's rate-determining step. Moreover, we found that the magnitude of the electric field exerted by the active site strongly correlates with the enzyme's catalytic rate enhancement, enabling us to quantify the fraction of the catalytic effect that is electrostatic in origin. The measurements described here may help explain the role of electrostatics in many other enzymes and biomolecular systems.
- Fried, Stephen D.,Bagchi, Sayan,Boxer, Steven G.
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- SYNTHESIS OF OPTICALLY ACTIVE (+)-19-NORTESTOSTERONE BY ASYMMETRIC BIS-ANNULATION REACTION
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Michael reaction of 1,7-octadien-3-one with 2-methylcyclopentane-1,3-dione, followed by intramolecular aldol condensation promoted by L-amino acids produced the optically active (+)-4-(3-butenyl)-7a-methyl-5,6,7,7a-tetrahydro-indane-1,5-dione in high chem
- Shimizu, Isao,Naito, Yoichiro,Tsuji, Jiro
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- Nitrobenzene as hydrogen acceptor in Pd/C-catalyzed hydrogen transfer reaction
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Nitrobenzene was found to work as an efficient hydrogen acceptor in the oxidation of allylic alcohols to give the corresponding enones in high yields.
- Tanaka, Takanori,Kawabata, Hirotoshi,Hayashi, Masahiko
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- Preparation method of [3-14C] marked 17alpha-estradiol
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The invention belongs to the technical field of synthesis of compounds marked by radioisotope 14C, and provides a preparation method of [3-14C] marked 17alpha-estradiol. The preparation method includes the following steps that 17beta-acylated elollactone and 14C marked acetylchloride serve as starting materials, and a condensation reaction, a primary hydrolysis reaction, a Mitsunobu reaction, an aromatization reaction and a secondary hydrolysis reaction are carried out to obtain [3-14C] marked 17alpha-estradiol. The method has the advantages that the synthesis cost is low, the line is short and the product yield is high. Besides, the preparation method is easy to operate and suitable for large-scale production.
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Paragraph 0089; 0098-0099
(2019/06/07)
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- Regio- and stereoselective reduction of 17-oxosteroids to 17β-hydroxysteroids by a yeast strain Zygowilliopsis sp. WY7905
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The reduction of 17-oxosteroids to 17β-hydroxysteroids is one of the important transformations for the preparation of many steroidal drugs and intermediates. The strain Zygowilliopsis sp. WY7905 was found to catalyze the reduction of C-17 carbonyl group of androst-4-ene-3,17-dione (AD) to give testosterone (TS) as the sole product by the constitutive 17β-hydroxysteroid dehydrogenase (17β-HSD). The optimal conditions for the reduction were pH 8.0 and 30 °C with supplementing 10 g/l glucose and 1% Tween 80 (w/v). Under the optimized transformation conditions, 0.75 g/l AD was reduced to a single product TS with >90% yield and >99% diastereomeric excess (de) within 24 h. This strain also reduced other 17-oxosteroids such as estrone, 3β-hydroxyandrost-5-en-17-one and norandrostenedione, to give the corresponding 17β-hydroxysteroids, while the C-3 and C-20 carbonyl groups were intact. The absence of by-products in this microbial 17β-reduction would facilitate the product purification. As such, the strain might serve as a useful biocatalyst for this important transformation.
- Liu, Yuanyuan,Wang, Yu,Chen, Xi,Wu, Qiaqing,Wang, Min,Zhu, Dunming,Ma, Yanhe
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- C-20 STEROID COMPOUNDS, COMPOSITIONS AND USES THEREOF TO TREAT TRAUMATIC BRAIN INJURY (TBI), INCLUDING CONCUSSIONS
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The present invention relates to C-20 steroid compounds, compositions and methods of use thereof to treat, minimize and/or prevent traumatic brain injury (TBI), including severe TBI, moderate TBI and mild TBI, including concussions.
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- HELIX 12 DIRECTED STEROIDAL PHARMACEUTICAL PRODUCTS
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Compounds having the structure or their salts: are used to treat or reduce le likelihood of acquiring androgen-dependent diseases, such as prostate cancer, benign prostatic hyperplasia, polycystic ovarian syndrome, acne, hirsutism, seborrhea, androgenic alopecia and male baldness. They can be formulated together with pharmaceutically acceptable diluent or carrier or otherwise made into any pharmaceutical dosage form. Some of these compounds having tissue-specific antiandrogenic activity and tissue-specific androgenic activity can be used to treat or reduce the risk of developing diseases related to loss of androgenic stimulation. Combinations with other active pharmaceutical agents are also disclosed.
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Page/Page column 71-72
(2010/02/12)
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- Anti-glaucomatous pharmaceutical composition and the process for obtaining them
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The invention relates to the domain of medicinal chemistry. It concerns more particularly that of the preparation of pharmaceutical compositions for ocular use. A subject of the invention is pharmaceutical compositions for ocular use characterized in that they contain at least one selected compound of steroidal structure in combination with or admixed with a pharmaceutically-acceptable, inert carrier or vehicle. The compositions according to the invention are intended to the treatment of glaucoma.
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- Synthesis of labelled [13C6]testosterone and [13C5]19-nortestosterone
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The condensation of ethyl acetoacetate-13C4 and ethyl bromoacetate-13C2 afforded, in seven steps, (1,2,3,4,5-13C5) 5-(diethylphosphono)-2-pentanone ethylene ketal 9. The reaction of this labelled compound with 7-[[(1,1-dimethylethyl)-dimethylsilyl]oxy]-1,6,6a,7,8, 9, 9a, 9b-octahydro-6a-methyl-[6aS-(6aa,7a,9aβ,9ba)] cyclopenta[f][1]benzopyran-3 (2H)-one 13 gave the benzindenone 14 which was converted to (1,2,3,4,10,19-13C6)testosterone 17 then, into (1,2,3,4,10-13C5)19-nortestosterone 18 by a reductive alkylation method.
- Joubert,Beney,Marsura,Luu-Duc
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p. 745 - 754
(2007/10/02)
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- Direct Conversion of 13β-Alkylgonatetraenes into 13β-Alkylgon-4-en-3-ones
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Birch reduction of 8,9-didehydroestradiol-17β 3-methyl ether 1 or 9(11)-didehydroestradiol-17β 3 methyl ether 2 followed by acid hydrolysis results in a mixture of 19-nortestosterone 8 and 19-nor-9β,10α-testosterone 9 in varying amounts.However, reduction of their acetates with sodium or lithium, tert-butyl alcohol in liquid ammonia and in the presence of aniline affords exclusively 19-nortestosterone.Similarly, 18α-homo-19-nortestosterone 12 is prepared from the acetate of 18α-homoestradiol-17β 3 methyl ether, 10.
- Bijoy, Panicker,Ramachandran, Uma,Rao, G. S. R. Subba
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p. 2331 - 2334
(2007/10/02)
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- Fluorine-18-Labeled Progestin Ketals: Synthesis and Target Tissue Uptake Selectivity of Potential Imaging Agents for Receptor-Positive Breast Tumors
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We have studied two new fluorine-substituted progestins as potential imaging agents for progesterone-receptor-positive human breast tumors. The steroids are 16α,17α-fluoroacetophenone ketals of 16α,17α-dihydroxyprogesterone and 16α,17α,21-trihydroxy-19-norprogesterone. Synthesis of the latter compound in seven steps from 19-norandrost-4-ene-3,17-dione is reported. Both compounds demonstrate high affinity for the progesterone receptor (PgR) (52.5 and 240percent, respectively, relative to R5020 = 100). The syntheses were adapted to 18F-labeling with 4'--fluoroacetophenone, prepared from 4'-nitroacetophenone by nucleophilic substitution with K18F/Kryptofix. Considerable adjustment of reaction conditions was required to effect ketalization using tracer quantities of the ketone. In tissue distribution studies in estrogen-primed immature female rats, both ketals showed selective uterine uptake, which was blocked by coinjection of a saturating dose of the unlabeled progestin ORG 2058. Additionally, metabolic stability of the radiolabel was indicated by the low radioactivity levels seen in bone. Both compounds showed relatively high uptake in fat, in accord with their relative lipophilicities demonstrated by HPLC-derived octanol-water partition coefficients. The selective uterine uptake and metabolic stability of these compounds suggests that this class of PgR ligands might be promising for the selective imaging of receptor-positive tumors if derivatives of reduced lipophilicity can be prepared.
- Kochanny, Monica J.,VanBrocklin, Henry F.,Kym, Philip R.,Carlson, Kathryn E.,O'Neil, James P.,et al.
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p. 1120 - 1127
(2007/10/02)
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- Photoinduced Molecular Transformations. Part 112.Transformation of Steroids into Ring-A-Aromatized Steroids and 19-Norsteroids involving a Regioselective β-Scission of Alkoxyl Radicals; Synthesis of Two Marine Natural Products, 19-Nor-5α-cholestan-3β-ol and 19-norcholest-4-en-3-one...
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A new transformation of steroids into 19-norsteroids and ring-A-aromatized steroids is described.The transformation method involves the removal of the 10β-methyl group by a regioselective β-scission of alkoxyl radicals.Cholesterol was transformed into two marine natural products, 19-nor-5α-cholestan-3β-ol and 19-norcholest-4-en-3-one, and into 19-norcholesta-1,3,5(10)-trien-3-ol.Transformations of 3β-hydroxyandrost-5-en-17-one into 19-nortestosterone, estrone, and the related estranes are also described.
- Suginome, Hiroshi,Senboku, Hisanori,Yamada, Shinji
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p. 2199 - 2205
(2007/10/02)
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- Microbiological Transformations. XIII. Transformations of 19-Nor and 19-Hydroxy Analogues of Testosterone and Androstendione by Means of Rhodotorula mucilaginosa Strain
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Preparative transformation carried out
- Dmochowska-Gladysz, Jadwiga,Tlomak, Elzbieta,Siewinski, Antoni
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- Synthesis of gon-4-enes
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1. A therapeutic composition having progestational activity comprising as active ingredient a 17-aliphatic carboxylic acid ester of 17α-ethynyl-18-methyl-19-nortestosterone and a pharmaceutical carrier for said compound.
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- Production of unsaturated carbocyclic ketones
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Preparation of α,β-unsaturated carbocyclic ketones by reacting an enol lactone with a carbanion generated by treatment of a methylphosphonate or a mono-substituted methylphosphonate with base.
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- Asymmetric synthesis of organic compounds
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Optically active organic compounds are prepared starting from optically inactive reactants by means of an optically active agent which influences the course of the reaction. In particular optically active compounds having a "meso" type carbon atom undergo an intramolecular ring closure in the presence of an optically active agent to yield an optically active product having one additional ring. The present process is particularly useful in the preparation of optically active bicyclic diketones which are important intermediates in the total synthesis of steroids.
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- Synthesis of 13-alkyl-gon-4-ones
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The preparation of 13-methylgon-4-enes and novel 13-polycarbonalkylgon-4-enes by a new total synthesis is described. 13-Alkylgon-4-enes having progestational, anabolic and androgenic activities are prepared by forming a tetracylic gonane structure unsaturated in the 1,3,5(10),9(11) and 14-positions, selectively reducing in the B- and C-rings, and converting the aromatic A-ring compounds so-produced to gon-4-enes by Birch reduction and hydrolysis.
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- Tetrahydropyran-2-ols
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Stereo-specific total synthesis of steroidal materials. 7-Substituted 3-oxo-1-heptenes or variants thereof are reacted with 2-alkylcycloalkane-1,3-diones yielding 3-substituted 6a β-alkyl-cyclopenta [f] [1] benzopyrans or naphtho [2,1-b] pyrans. These are then subjected to a selective catalytic hydrogenation followed by an introduction of a hydroxy, alkoxy or acyloxy group at the 4a-position to produce a 3-substituted 6a β,4a-hydroxy, alkoxy or acyloxy perhydrocyclopenta [f] [1] benzopyran or perhydro-naphtho [2,1-b] pyran. These latter compounds are then converted into 4- or 5-(3-oxoalkyl)perhydroindene-5-ones or perhydronaphthalene-6-ones which in turn can be converted to known steroidal materials by known methods.
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