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Journal articles on the topic 'Β-unsaturated steroids'

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Published: 4 June 2025

Last updated: 1 August 2025

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1

Chodounská, Hana, та Vladimír Pouzar. "Preparation of 3-(6-Deoxy-β-D-glucopyranosyloxy) and 3-(6-Deoxy-α-L-mannopyranosyloxy)androstane Derivatives with Unsaturated Side Chain in Position 17β". Collection of Czechoslovak Chemical Communications 58, № 12 (1993): 3000–3008. http://dx.doi.org/10.1135/cccc19933000.

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In our previous papers we described the preparation of 3-β-D-glucopyranosyloxy) and 3-β-D-galactopyranosyloxy) derivatives of steroids with an α,β-unsaturated ester chain in position 17β of androstane skeleton. In conection with this project we have studied silver silicate promoted glycosylation of some of above mentioned steroidal derivatives with 2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranosyl bromide and 2,3,4-tri-O-acetyl-6-deoxy-α-L-mannopyranosyl bromide.

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2

Xia, Zi-Yi, Man-Man Sun, Yang Jin, et al. "Lobosteroids A–F: Six New Highly Oxidized Steroids from the Chinese Soft Coral Lobophytum sp." Marine Drugs 21, no. 8 (2023): 457. http://dx.doi.org/10.3390/md21080457.

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To explore the steroidal constituents of the soft coral Lobophytum sp. at the coast of Xuwen County, Guangdong Province, China, a chemical investigation of the above-mentioned soft coral was carried out. After repeated column chromatography over silica gel, Sephadex LH-20, and reversed-phase HPLC, six new steroids, namely lobosteroids A–F (1–6), along with four known compounds 7–10, were obtained. Their structures were determined by extensive spectroscopic analysis and comparison with the spectral data reported in the literature. Among them, the absolute configuration of 1 was determined by X-

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3

Parish, Edward J., Huaizhong Li та Shengrong Li. "Facile β-Epoxidation of Unsaturated Steroids with Permanganateion". Synthetic Communications 25, № 6 (1995): 927–40. http://dx.doi.org/10.1080/00397919508013431.

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4

Dénès, Fabrice, Julien Farard, and Jacques Lebreton. "Synthesis of 13C-Labeled Steroids." Synthesis 51, no. 23 (2019): 4311–37. http://dx.doi.org/10.1055/s-0037-1611914.

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Due to the wide spectrum of biological activities of steroids, the detection and quantification of steroidal residues in various biological materials are crucial for drug development, doping prevention, and environmental protection. In addition, the analytical technique of stable isotopic dilution (SID) by Liquid Chromatography-Mass Spectrometry (LC-MS) requires 13C-labeled steroids as standards to provide accurate and reproducible steroid quantification. In this context, the synthesis of 13C-labeled steroids is reviewed. The approaches based on partial synthesis starting from commercially ava

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5

Živković, Marijana B., Irena T. Novaković, Ivana Z. Matić, Dušan Sladić та Natalija M. Krstić. "Synthesis and preliminary screening for the biological activity of some steroidal Δ 4 -unsaturated semicarbazone derivatives". Steroids 148 (20 квітня 2019): 36–46. https://doi.org/10.1016/j.steroids.2019.04.010.

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Eleven new steroidal mono- and bis(semicarbazones)2a–e, 4d and 3a–e have been prepared starting from various 3-oxo-α,β-unsaturated steroids. Mono-semicarbazones 2a–e were further subjected to ethyl chloroacetate in boiling absolute ethanol but, instead of expected intramolecular cyclocondensation reaction products, the new carbazate esters 5a-e were obtained. The structures of all synthesized compounds and identification of each E/Z isomer were deduced by elemental analysis, HRMS, NMR, and IR spectroscopy. Preliminary screening for the cytotoxic activity in vitro o

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6

Mesa, Dayana, Yarelys E. Augusto, Giselle Hernández та ін. "The Synthesis of Novel aza-Steroids and α, β-Unsaturated-Cyanoketone from Diosgenin". Molecules 28, № 21 (2023): 7283. http://dx.doi.org/10.3390/molecules28217283.

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Recent studies have demonstrated the antiproliferative and cytotoxic effects of aza-steroids and steroidal sapogenins on human cancer cell lines. The scientific community has shown a growing interest in these compounds as drug candidates for cancer treatment. In the current work, we report the synthesis of new diosgenin oxime derivatives as potential antiproliferative agents. From (25 R)-5α-spirost-3,5,6-triol (1), a diosgenin derivative, ketones 2, 3, 4, and 9 were obtained and used as precursors of the new oximes. A condensation reaction was carried out between the steroidal ketones (2, 3, 4

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7

Grześ, Paweł A., Bonifacio Monti, Natalia Wawrusiewicz-Kurylonek, et al. "Simple Zn-Mediated Seleno- and Thio-Functionalization of Steroids at C-1 Position." International Journal of Molecular Sciences 23, no. 6 (2022): 3022. http://dx.doi.org/10.3390/ijms23063022.

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Here we report the reaction in the biphasic system of the in situ prepared selenols and thiols with 1,4-androstadiene-3,17-dione (1) or prednisone acetate (2) having α,β-unsaturated ketone as an electrophilic functionalization. The Michael-type addition reaction resulted to be chemo- and stereoselective, affording a series of novel steroidal selenides and sulfides. This is an example of a one-step, eco-friendly process that bypasses some of the main concerns connected with the bad smell and the toxicity of these seleno- and thio-reagents. Furthermore, we demonstrated that the proposed methodol

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8

Cortés-Percino, Alejandra, José Luis Vega-Báez, Anabel Romero-López, et al. "Synthesis and Evaluation of Pyrimidine Steroids as Antiproliferative Agents." Molecules 24, no. 20 (2019): 3676. http://dx.doi.org/10.3390/molecules24203676.

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A small and focused library of steroidal non-fused and fused pyrimidines was prepared from pregnenolone acetate and diosgenin, respectively. The key step was the cycloaddition reaction of nitrogen-containing 1,3-binucleophiles with the steroidal α,β-unsaturated ketone. Urea, thiourea and guanidine reacted in a similar manner and afforded the steroidal pyrimidines in good yields. The antiproliferative tests against human tumor cell lines gave GI50 values in the micromolar range and had no effect on healthy fibroblasts. Additional experiments indicated that the compounds did not act as P-glycopr

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9

Tavarès, Manuella, René Ramasseul, Jean-Claude Marchon, Bernard Bachet, Claude Brassy та Jean-Paul Mornon. "Catalytic β-stereospecific epoxidation of unsaturated steroids by trans-dioxoruthenium(VI)tetramesitylporphyrin. Stereochemical grounds for the β-diastereofacial selection". J. Chem. Soc., Perkin Trans. 2, № 8 (1992): 1321–29. http://dx.doi.org/10.1039/p29920001321.

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10

Salvador, J. A. R., M. L. Sáe Melo та A. S. Campos Neves. "Oxidations with potassium permanganate — metal sulphates and nitrates. β-Selective epoxidation of Δ5-unsaturated steroids". Tetrahedron Letters 37, № 5 (1996): 687–90. http://dx.doi.org/10.1016/0040-4039(95)02243-0.

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11

Booth, W. D., and C. A. White. "The isolation, purification and some properties of pheromaxein, the pheromonal steroid-binding protein, in porcine submaxillary glands and saliva." Journal of Endocrinology 118, no. 1 (1988): 47—NP. http://dx.doi.org/10.1677/joe.0.1180047.

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ABSTRACT Pheromaxein, the 16-androstene steroid-binding protein with a relative molecular mass of 15 000 was isolated in sub-milligram quantities from the submaxillary gland and saliva of the Gottingen miniature boar, after a fourfold purification involving the following methods: ultrafiltration for submaxillary gland cytosols and ethanol precipitation for saliva, Concanavalin-A-Sepharose affinity chromatography, sodium dodecyl sulphate polyacrylamide gel electrophoresis, 'Extractigel-D' affinity chromatography (to remove sodium dodecyl sulphate) and fast protein-liquid chromatography. Yields

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12

Moussa, Senigra, Oum Elkhair Rahim, Rezkallah Chafika, Ammar Haouat, and Ghemam Amara Djilani. "Identification, quantification, and antioxidant capacity of active compounds in Fagonia cretica organic extracts." Brazilian Journal of Animal and Environmental Research 7, no. 4 (2024): e76066. https://doi.org/10.34188/bjaerv7n4-141.

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This study aims to identify and quantify the active compounds and antioxidant capacity for scavenging free radicals in the organic extracts of *Fagonia cretica*. Extracts were prepared based on the polarity differences of solvents from the dried plant material, starting with the hydromethanolic extract, followed by fractionation into n-hexane, chloroform, ethyl acetate, and 1-butanol, respectively. The following compounds were evaluated: saponins, tannins, steroids, terpenes, cardenolides, flavonoids, coumarins, saturated and unsaturated steroids, along with the estimation of phenolic and flav

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13

SYAMALA, M. S., J. DAS, S. BASKARAN та S. CHANDRASEKARAN. "ChemInform Abstract: A Novel and Highly β-Selective Epoxidation of δ5- Unsaturated Steroids with Permanganate Ion." ChemInform 23, № 38 (2010): no. http://dx.doi.org/10.1002/chin.199238234.

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14

TAVARES, M., R. RAMASSEUL, J. C. MARCHON, B. BACHET, C. BRASSY та J. P. MORNON. "ChemInform Abstract: Catalytic β-Stereospecific Epoxidation of Unsaturated Steroids by trans-Dioxoruthenium(VI)tetramesitylporphyrin. Stereochemical Grounds for the β-Diastereofacial Selection." ChemInform 23, № 48 (2010): no. http://dx.doi.org/10.1002/chin.199248257.

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15

Mostinski, Yelena, David Lankri, and Dmitry Tsvelikhovsky. "Transition-Metal-Catalyzed Synthesis of Spirolactones." Synthesis 49, no. 11 (2017): 2361–73. http://dx.doi.org/10.1055/s-0036-1588783.

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Spiranoid lactone structures can frequently be observed as scaffold segments of various biochemical compounds and drugs of natural origin. Examples of these structures have been identified among terpenoids, alkaloids, steroids, carbohydrates, and many other natural products. Such a broad natural diversity and biological activity allows a wide spectrum of these systems to be attractive targets for synthetic and medicinal chemists. Covering a broad spectrum of recognized approaches toward the design of spirolactones established over the past several decades, this review focuses on transition-met

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16

Kesavan, Venkitasamy, та Srinivasan Chandrasekaran. "A Highly β-Stereoselective Catalytic Epoxidation of Δ5-Unsaturated Steroids with a Novel Ruthenium(II) Complex under Aerobic Conditions". Journal of Organic Chemistry 63, № 20 (1998): 6999–7001. http://dx.doi.org/10.1021/jo980829k.

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17

Zhao, Yuan-Cong, Yong-Ze Xiang, Lin Pu, Meng Yang та Xiao-Qi Yu. "Highly β-selective epoxidation of the Δ5- and Δ4-unsaturated steroids catalyzed by the silica-supported polyhalogenated ruthenium porphyrin". Applied Catalysis A: General 301, № 2 (2006): 176–81. http://dx.doi.org/10.1016/j.apcata.2005.11.025.

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18

Qadir, Abdul, Athar Ali, Muhammad Arif, et al. "Solvent Extraction and GC-MS Analysis of Sesame Seeds for Determination of Bioactive Antioxidant Fatty Acid/Fatty Oil Components." Drug Research 68, no. 06 (2017): 344–48. http://dx.doi.org/10.1055/s-0043-123466.

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AbstractThe seed kernels of Sesamum indicum L. (family: Pedaliaceae) were extracted with ethanol and yield of components determined by Gas Chromatography/Mass Spectrometry (GC/MS). The free radical scavenging activities of ethanolic extract against1, 1-Diphenyl-2-picrylhydrazyl (DPPH) were determined by UV spectrophotometer at 517 nm. Phytochemical screening revealed the presence of numerous bioactive compounds including steroids, phenolic, terpenoids, fatty acids and different types of ester compounds. The ethanolic extract was purified and analyzed by GC MS.The prevailing compounds found in

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19

Serebrennikova, Olga Viktorovna, Eugenia Borisovna Strelnikova, and Irina Vladimirovna Russkikh. "CHROMATOMASS SPECTROMETRIC STUDY OF LEAVES OF RUBUS IDAEUS L. AND SORBUS AUCUPARIA L. SOUTH OF THE TOMSK REGION." chemistry of plant raw material, no. 2 (May 22, 2024): First. http://dx.doi.org/10.14258/jcprm.20240212935.

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The features of the distribution of fat-soluble organic compounds in the leaves of deciduous shrubs Rubus idaeus and Sorbus aucuparia growing in identical weather conditions in mixed and pine forests of the southern taiga of Western Siberia are shown. The composition of n-alkanes, saturated and unsaturated fatty acids, n-aldehydes, n-alkane-2-ones, n-alkanols, acyclic isoprenoids, steroids and pentacyclic triterpenoids was studied by chromatomass spectrometry. It was found that the microclimate of pine forest and mixed forest influences the composition of organic compounds in the leaves of sin

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20

KESAVAN, V., та S. CHANDRASEKARAN. "ChemInform Abstract: A Highly β-Stereoselective Catalytic Epoxidation of Δ5-Unsaturated Steroids with a Novel Ruthenium(II) Complex under Aerobic Conditions." ChemInform 30, № 6 (2010): no. http://dx.doi.org/10.1002/chin.199906170.

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21

Hantos, Susanne M., Sasmita Tripathy, Najma Alibhai, and Tony Durst. "Synthesis of trichiliasterones A and B 16-Ketosteroids isolated from Trichilia hirta and Trichilia americana." Canadian Journal of Chemistry 79, no. 11 (2001): 1747–53. http://dx.doi.org/10.1139/v01-126.

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The syntheses of trichiliasterone A (3β-hydroxypregnan-2,16-dione) and trichiliasterone B (2-hydroxyandrost-1,4-diene-3,16-dione) have been carried out starting from isoandrosterone and testosterone acetate, respectively. In each synthesis the functionality in the D ring was installed prior to working on ring A. In the case of trichiliasterone A, the D ring chemistry involved a Wittig reaction to generate the 17-methylene group, followed by SeO2 oxidation to give an α,β-unsaturated ketone. Reaction with lithium dimethyl cuprate gave the required 17-ethyl-16-keto functionality. A 2,3-epoxy enol

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22

Ishar, M. P. S., N. K. Girdhar, K. Kumar, Rama Rama та S. Kaur. "ChemInform Abstract: Investigations on Photochemical Linking of Steroids with Amino Acids: Irradiation of α,β-Unsaturated Steroidal Ketones in the Presence of Amino Acids in Aqueous Medium." ChemInform 31, № 16 (2010): no. http://dx.doi.org/10.1002/chin.200016199.

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23

Tung, Yu-Tang, Chun-Hsu Pan, Yi-Wen Chien, and Hui-Yu Huang. "Edible Mushrooms: Novel Medicinal Agents to Combat Metabolic Syndrome and Associated Diseases." Current Pharmaceutical Design 26, no. 39 (2020): 4970–81. http://dx.doi.org/10.2174/1381612826666200831151316.

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Metabolic syndrome is an aggregation of conditions and associated with an increased risk of developing diabetes, obesity and cardiovascular diseases (CVD). Edible mushrooms are widely consumed in many countries and are valuable components of the diet because of their attractive taste, aroma, and nutritional value. Medicinal mushrooms are higher fungi with additional nutraceutical attributes having low-fat content and a transisomer of unsaturated fatty acids along with high fiber content, biologically active compounds such as polysaccharides or polysaccharide β-glucans, alkaloids, steroids, pol

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24

Bertsch, Andreas, Horst Schweer, and Andreas Titze. "Analysis of the Labial Gland Secretions of the Male Bumblebee Bombus griseocollis (Hymenoptera: Apidae)." Zeitschrift für Naturforschung C 59, no. 9-10 (2004): 701–7. http://dx.doi.org/10.1515/znc-2004-9-1015.

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Abstract The labial gland secretions from males of the bumblebee Bombus (Separatobombus) griseocollis De Geer, a bumblebee exhibiting perching behaviour, were analysed by gas chromatography/ mass spectrometry (GC/MS) in the electron impact and positive ion chemical ionization mode. The major compound of the complex mixture of alkenols, acetates, hydrocarbons, wax type esters and steroids is tetradecyl acetate, considerable amounts of hexadecyl, geranyllinaloyl, geranylgeranyl, docosyl, tetracosenyl and hexacosenyl acetate were also found. 1,3-Tetradecanediol diacetate, detected as a minor comp

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25

Čobeljić, Božidar R., Marijana B. Živković, Ivana Z. Matić, et al. "Synthesis, characterization and biological activity of pt(ii) complexes with steroidal thiosemicarbazones." J Serb Chem Soc 85, no. 5 (2021): 459–68. https://doi.org/10.2298/JSC201211083C.

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Abstract: In this work, Pt(II) complexes of previously synthesized steroidal thiosemicarbazones were synthesized and characterized. The ligands and their metal complexes were studied by analytical and spectroscopic data (elemental analysis, IR, 1D NMR and 2D NMR, HSQC, HMBC, NOESY, COSY), the analysis of which enabled complete 1H and 13C assignments of each compound including E and Z isomers. All the synthesized ligands and complexes were screened for their cytotoxic and antimicrobial activity. The results demonstrate that new steroidal thiosemicarbazone complexes were significantly less cytot

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26

Zaretskii, Z. V. I., J. M. Curtis, A. G. Brenton та J. H. Beynon. "Translational energy release and stereochemistry of steroids. XI—Determination of the configuration of α,β-unsaturated 3-keto steroid alcohols with the hydroxyl group in rings C and D". Organic Mass Spectrometry 23, № 7 (1988): 511–16. http://dx.doi.org/10.1002/oms.1210230703.

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27

CHODOUNSKA, H., та V. POUZAR. "ChemInform Abstract: Steroids. Part 371. Preparation of 3-(6-Deoxy-β-D-glucopyranosyloxy) and 3-(6-Deoxy-α-L-mannopyranosyloxy)androstane Derivatives with Unsaturated Side Chain in Position 17β." ChemInform 25, № 14 (2010): no. http://dx.doi.org/10.1002/chin.199414265.

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28

Hansen, CH, B. Fraiture, R. Rouhi, E. Otto, G. Förster, and G. Kahaly. "HPLC Glycosaminoglycan Analysis in Patients with Graves' Disease." Clinical Science 92, no. 5 (1997): 511–17. http://dx.doi.org/10.1042/cs0920511.

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1. Orbital accumulation of hydrophilic, interstitial glycosaminoglycans (GAGs) and subsequent expansion of retrobulbar tissue lead to the clinical manifestation of exophthalmos in patients with Graves' eye disease. 2. A highly specific method to determine the concentration and biochemical composition of different GAGs was developed in order to obtain a sensitive test system for the activity of the disease. By means of this method, GAG excretion in 24 h urine collections of 56 patients and 21 controls was analysed by precipitation with cetylpyridinium chloride and potassium acetate in ethanol,

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29

Radman, Sanja, Ana-Marija Cikoš, Sanja Babić, et al. "In Vivo and In Vitro Antioxidant Activity of Less Polar Fractions of Dasycladus vermicularis (Scopoli) Krasser 1898 and the Chemical Composition of Fractions and Macroalga Volatilome." Pharmaceuticals 15, no. 6 (2022): 743. http://dx.doi.org/10.3390/ph15060743.

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The present research is a comprehensive investigation of Dasycladus vermicularis (Scopoli) Krasser 1898 from the Adriatic Sea (Croatia) regarding volatilome–volatile organic compounds (VOCs, mostly nonpolar compounds) and less polar nonvolatile compounds for the first time. Headspace solid-phase microextraction (HS-SPME) and hydrodistillation (HD) were used showing the great volatilome variability among fresh (HS-FrDV and HD-FrDV) and dried (HS-DrDV and HD-DrDV) samples after GC–MS analysis. Aromatic aldehydes were dominant in both fresh and air-dried HS samples with benzaldehyde as the most a

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30

Černý, Ivan, Vladimír Pouzar, Pavel Drašar та Miroslav Havel. "β-Glucosides of steroidal unsaturated nitriles". Collection of Czechoslovak Chemical Communications 52, № 10 (1987): 2521–33. http://dx.doi.org/10.1135/cccc19872521.

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Reaction of 3β-methoxymethoxy-5-pregnen-20-one (Ia) with diethyl cyanomethylphosphonate and subsequent removal of the protecting group afforded (20E)-3β-hydroxy-24-norchola-5,20(22)-diene-23-nitrile (IIIa). Besides the analogous derivative IIIb with another double bond in position 14, the fully saturated compounds IIIc and IIId with configuration 5α and 5β, respectively, were prepared similarly. Silver silicate-catalyzed glycosylation of IIIa-IIId with tetra-O-acetyl-α-D-glucopyranosyl bromide gave β-D-glucopyranosides IVa-IVd in 77-89% yield. A parallel series of hemisuccinates VIa-VId was pr

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31

López-Pérez, Borja, Miguel A. Maestro та Antonio Mouriño. "Total synthesis of 1α,25-dihydroxyvitamin D3 (calcitriol) through a Si-assisted allylic substitution". Chemical Communications 53, № 58 (2017): 8144–47. http://dx.doi.org/10.1039/c7cc04690a.

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A total synthesis of calcitriol through a Si-assisted substitution to generate the trans-hydrindane core and an asymmetric CuH-catalyzed 1,4-reduction of α,β,γ,δ-unsaturated ester to access the steroid configuration at C20 is described.

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32

Krstić, Natalija M., Mira S. Bjelaković, Milan M. Dabović та Vladimir D. Pavlović. "Thionation of Some α,β-Unsaturated Steroidal Ketones". Molecules 15, № 5 (2010): 3462–77. http://dx.doi.org/10.3390/molecules15053462.

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33

Iglesias-Arteaga, Martin A., та Juan E. Hernández-Martínez. "BF3·OEt2-Catalyzed Aldol Condensation of Steroid Sapogenins and 2-Oxoacids: A Single Step Conversion of Steroid Spiroketals into Branched α,β-Unsaturated Spirolactones". Synthesis 52, № 15 (2020): 2241–44. http://dx.doi.org/10.1055/s-0040-1708018.

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BF3·OEt2-catalyzed aldol reaction of steroid sapogenins with glyoxylic acid or pyruvic acid led to compounds in which the novel spirocyclic side chain bears an α,β-unsaturated lactone. The structures of the new spirolactones were established with the aid of combined 1D and 2D NMR techniques. A plausible mechanism is described.

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34

Pouzar, Vladimír, Ivan Černý, Pavel Drašar, and Miroslav Havel. "New approach to steroidal hemisuccinates and glycosides." Collection of Czechoslovak Chemical Communications 52, no. 3 (1987): 775–87. http://dx.doi.org/10.1135/cccc19870775.

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New synthesis of hemisuccinate and β-D-glucopyranoside of (20E)-21-ethoxycarbonyl-5,20-pregnadien-3β-ol (XVIII and XXVI) is described, consisting in the preparation of a protected hemisuccinate (XV) or glucoside (XXIII) intermediate, into which the unsaturated ester grouping in the side-chain is incorporated only in the final stage of the synthesis. The primary hydroxyl at C(20) was protected by tert-butyldimethylsilyl, trityl or nitrate groups, the succinate was blocked with 2-(trimethylsilyl)ethyl or 2,2,2-trichloroethyl groups and the glucosides were used in the form of peracetyl derivative

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35

Gogoi, Junali, Pranjal Gogoi, Pranjal Bezbaruah та Romesh C. Boruah. "Microwave-assisted Pd-catalyzed synthesis of fused steroidal and non-steroidal pyrimidines from β-halo-α,β-unsaturated aldehydes". Tetrahedron Letters 54, № 52 (2013): 7136–39. http://dx.doi.org/10.1016/j.tetlet.2013.10.094.

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36

Kuball, H. G., S. Neubrech та A. Schönhofer. "Optical activity of oriented molecules. α,β-unsaturated steroid ketones and their sector rules". Chemical Physics 163, № 1 (1992): 115–32. http://dx.doi.org/10.1016/0301-0104(92)80146-m.

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37

Frelek, Jadwiga, Wojciech J. Szczepek та Hans Peter Weiß. "Circular dichroism of steroidal and related cisoid α,β-unsaturated ketones. Part I." Tetrahedron: Asymmetry 4, № 3 (1993): 411–24. http://dx.doi.org/10.1016/s0957-4166(00)86086-3.

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38

Qinjian, Zhao, та Li Zhensu. "Preparative separation and properties of (E)- and (Z)-steroidal α,β-unsaturated ketoximes". Journal of Chromatography A 635, № 2 (1993): 342–45. http://dx.doi.org/10.1016/0021-9673(93)80379-m.

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39

Frelek, Jadwiga, Wojciech J. Szczepek та Hans Peter Weiß. "Circular dichroism of steroidal and related cisoid α,β-unsaturated ketones. Part II". Tetrahedron: Asymmetry 6, № 6 (1995): 1419–30. http://dx.doi.org/10.1016/0957-4166(95)00175-o.

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40

Suginome, Hiroshi, та Takashi Ohki. "A new photoinduced rearrangement of steroidal α,β-unsaturated cyclic ketone oximes into the β,γ-unsaturated isomer involving an intramolecular stereospecific hydrogen transfer". J. Chem. Soc., Chem. Commun., № 23 (1988): 1568–70. http://dx.doi.org/10.1039/c39880001568.

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41

Ricigliano, J. W., та T. M. Penning. "Evidence that enzyme-generated aromatic Michael acceptors covalently modify the nucleotide-binding site of 3α-hydroxysteroid dehydrogenase". Biochemical Journal 269, № 3 (1990): 749–55. http://dx.doi.org/10.1042/bj2690749.

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The non-steroidal allylic and acetylenic alcohols 1-(4′-nitrophenyl)prop-2-en-1-ol (I) and 1-(4′-nitrophenyl)prop-2-yn-1-ol (II) are oxidized by homogeneous 3 alpha-hydroxysteroid dehydrogenase to the corresponding alpha β-unsaturated ketones 1-(4′-nitrophenyl)prop-2-en-1-one (III) and 1-(4′-nitrophenyl)prop-2-yn-1-one (IV), which then inactivate the enzyme selectively with high affinity; low effective partition ratios are observed for the parent alcohols [Ricigliano & Penning (1989) Biochem. J. 262, 139-149]. Inactivation of 3 alpha-hydroxysteroid dehydrogenase by compound (I) displays an

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Yaremenko, F. G., N. S. Pivnenko, L. A. Kutulya, Zh A. Kondratyuk, N. B. Novikova та N. I. Shkolnikova. "New steroid α,β-unsaturated ketones as chiral components of induced cholesteric liquid crystal systems". Russian Chemical Bulletin 58, № 5 (2009): 1072–83. http://dx.doi.org/10.1007/s11172-009-0137-9.

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Neef, G., E. Ottow, G. Ast та H. Vierhufe. "Ceric(IV)Ammonium Nitrate Catalyzed Nucleophilic Opening of a Steroidal α,β-Unsaturated Epoxide". Synthetic Communications 23, № 7 (1993): 903–11. http://dx.doi.org/10.1080/00397919308013287.

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Suginome, Hiroshi, Makoto Kaji, Toshiharu Ohtsuka, Shinji Yamada та Akio Furusaki. "A new stereospecific rearrangement of an excited steroidal α,β-unsaturated cyclic ketone oxime". J. Chem. Soc., Chem. Commun., № 4 (1987): 283–84. http://dx.doi.org/10.1039/c39870000283.

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Suginome, Hiroshi, Takashi Ohki, Atsushi Nagaoka та Hisanori Senboku. "Photoinduced molecular transformations. Part 133. New photoinduced deconjugation of steroidal α,β-unsaturated cyclic ketone oxime into the β,γ-unsaturated isomer involving stereospecific proton transfer". J. Chem. Soc., Perkin Trans. 1, № 14 (1992): 1849–54. http://dx.doi.org/10.1039/p19920001849.

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Edwards, O. E., J. L. Douglas, D. C. Horwell, W. Rank та T. Sano. "Thermal and photochemical reactions of steroidal α-azido ketones". Canadian Journal of Chemistry 70, № 9 (1992): 2405–12. http://dx.doi.org/10.1139/v92-305.

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Photolysis of 9α-azido-3β,20β-diacetoxy-5α-pregnan-11-one in methanol gave the N-acyl imine 11-aza-3β,20β-diacetoxy-C-homo-5α-pregn-9,11-en-12-one 4 and the aminoketone 9a-aza-3β,20β-diacetoxy-9-methoxy-B-homo-5α-pregnan-11-one 7. In dichloromethane containing triethylamine the irradiation of this azide gave the N-acyl imine 4 and the α,β-unsaturated amino ketone 9a-aza-3β,20β-diacetoxy-B-homo-5α-pregn-8-en-11-one 8. Thermolysis or photolysis of 12α-azido-3α,20β-diacetoxy-5β-pregnan-11-one gave the N-acyl imine 12-aza-3α,20β-diacetoxy-C-homo-5β-pregn-12-en-11-one 10 as major product. Photolysi

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FRELEK, J., W. J. SZCZEPEK та H. P. WEISS. "ChemInform Abstract: Circular Dichroism of Steroidal and Related Cisoid α,β- Unsaturated Ketones. Part 1." ChemInform 24, № 29 (2010): no. http://dx.doi.org/10.1002/chin.199329226.

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SUGINOME, H., T. OHKI, A. NAGAOKA та H. SENBOKU. "ChemInform Abstract: Photoinduced Molecular Transformations. Part 133. New Photoinduced Deconjugation of Steroidal α,β-Unsaturated Cyclic Ketone Oxime into the β,γ-Unsaturated Isomer Involving Stereospecific Proton Transfer." ChemInform 23, № 45 (2010): no. http://dx.doi.org/10.1002/chin.199245246.

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Ghosh, Pranab, Antara Sarkar та Jayanta Das. "Mercuric(II) Acetate Oxidation of Steroidal Exocyclic α,β-Unsaturated Ketone: Transformation into a Cyclic Ether". Molbank 2009, № 3 (2009): M616. http://dx.doi.org/10.3390/m616.

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Parish, Edward J., Mitsuhiro Tsuda та G. J. Schorepfer. "Stereospecific 1,4-addition to an α,β-unsaturated steroidal epoxide: syntheses of new 15-oxygenated sterols". Chemistry and Physics of Lipids 49, № 1-2 (1988): 119–29. http://dx.doi.org/10.1016/0009-3084(88)90073-4.

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