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Journal articles on the topic 'Pregnа-5'

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Published: 4 June 2025

Last updated: 15 July 2025

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1

О., В. Булавенко, В. Фурман О., А. Таран О., and Л. Льовкіна О. "A MODERN OBSTETRICIAN-GYNECOLOGISTS' VIEW ON THE MULTIVITAMIN COMPLEXES FOR PREGNANT WOMEN." REPRODUCTIVE ENDOCRINOLOGY, no. 47 (June 30, 2019): 64–67. https://doi.org/10.18370/2309-4117.2019.47.64-67.

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During pregnancy, especially in the second and third trimesters, the need of pregnant woman's body for plastic and biologically active substances, which are later used to build the fetus organs and systems, significantly increases. The lack of certain vitamins, minerals and trace elements during pregnancy negatively affects the health of women and fetus, thereby increasing the risk of perinatal pathology and infant mortality, as well as the frequency of prematurity, congenital malformations, disorders of physical and mental child development. Milk secretion during lactation also contributes to the gradual depletion of vitamins and minerals in the woman body. Completing the lack of certain vitamins and microelements during pregnancy by additional unbalanced food intake, which contains the necessary micronutrients, is usually accompanied by an excessive increase in weight and increase in fetal weight, which leads to birth trauma and other complications. Therefore, even a balanced diet of a pregnant woman cannot fully satisfy her needs for vitamins and trace elements. Therefore, the use of dietary supplements during pregnancy and lactation is extremely necessary for every woman. The most favorable and rational solution to prevent the micronutrient deficiencies is the regular use of special dietary supplements for pregnant women, which include the dietary supplement Pregna-5 from Amaxa Pharma. Its feature and the main difference from other drugs of this group, presented in Ukraine, that it contains exactly those nutrients, which recommended amount is difficult to obtain with balanced diet. Pregna-5 contains ω-3 polyunsaturated fatty acid (specifically docosohexaenoic acid) in a dosage of 250 μg. Also this drug contains vitamin D3 (cholecalciferol) – 2000 MI, iodine – 200 mg, folates – 800 mg, iron – 30 mg.

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2

Gonzalez, Mario D., and Gerardo Burton. "On the Elimination of the 3-Benzylthioenol Ether of Pregn-4-ene-3,20-dione by W-2 Raney Nickel." Zeitschrift für Naturforschung B 40, no. 5 (1985): 639–44. http://dx.doi.org/10.1515/znb-1985-0513.

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Reaction of 3-benzylthiopregna-3,5-dien-20-one or of pregna-3,5-dien-20-one with W-2 Raney nickel in acetone afforded a mixture of 20-ketopregnanes with different degrees of insaturation on rings A and B, of which the main component was identified as pregn-2-en-20-one. When deactivated Raney nickel was used, the main product was the expected pregna-3,5-dien-20-one with minor amounts of pregn-4-en-20-one and pregn-5-en-20-one.

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3

Polman, Jiří, та Alexander Kasal. "Synthesis of 5-methyl-19-nor-5β-pregn-9-ene derivatives". Collection of Czechoslovak Chemical Communications 55, № 7 (1990): 1783–91. http://dx.doi.org/10.1135/cccc19901783.

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3β,5,6β-Trihydroxy-5α-pregnan-20-one 3-pivalate (I) was converted into 3β,6β-dihydroxy-5-methyl-19-nor-5β-pregn-9-en-20-one 3-pivalate 5-acetate (II) under conditions of Westphalen rearrangement. Deoxygenation in the position 6β was effected by treatment of the corresponding 6β-thiobenzoate or thioimidazolide with tributyltin hydride. Progesterone analogues XII and XIII, prepared from the 6-deoxy compound IX, exhibit abortive activity.

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4

Chodounská, Hana, та Alexander Kasal. "Epalons: Synthesis of 3α,7α-Dihydroxy-5α-pregnan-20-one". Collection of Czechoslovak Chemical Communications 63, № 10 (1998): 1543–48. http://dx.doi.org/10.1135/cccc19981543.

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3α,7α-Dihydroxy-5α-pregnan-20-one (12) was prepared from (20R)-pregn-5-ene-3β,20-diyl 3-acetate 20-benzoate (1). ∆5-Olefin was oxidized in an allylic position and hydrogenated. Inversion of a configuration at carbon C-3 was carried out by solvolysis in N,N-dimethylformamide of 3β-tosylate in the presence of sodium nitrite. For stereoselective reduction of the 7-oxo group, L-Selectride® was used.

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5

Scott, A. P., A. V. M. Canario, Nancy M. Sherwood та Carol M. Warby. "Levels of steroids, including cortisol and 17α,20β-dihydroxy-4-pregnen-3-one, in plasma, seminal fluid, and urine of Pacific herring (Clupea hareng us pallasi) and North Sea plaice (Pleuronectes platessa L.)". Canadian Journal of Zoology 69, № 1 (1991): 111–16. http://dx.doi.org/10.1139/z91-016.

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In an accompanying paper we report that herring milt contains high concentrations of conjugated cortisol and 17α,20β-dihydroxy-4-pregnen-3-one. We suggest that one source of these steroids was the urine, which could have become mixed with the milt during the hand-stripping procedure. In the present study, samples of hand-stripped milt from several other species, plaice (Pleuronectes platessa), dab (Limanda limanda), flounder (Platichthys flesus), goldfish (Carassius auratus), and rainbow trout (Oncorhynchus mykiss, formerly Salmo gairdneri), were assayed for free and conjugated cortisol. Uncontaminated samples of plasma, seminal fluid, and urine of male herring and plaice were also assayed for free and conjugated cortisol (both species), 17α,20β-dihydroxy-4-pregnen-3-one (herring only), 17α,20α-dihydroxy-4-pregnen-3-one, and 3α,17α,21-trihydroxy-5β-pregnan-20-one (plaice only). The results showed that hand-stripped milt from these other species, excluding rainbow trout (from which it was possible to obtain urine-free milt), also had markedly high levels of conjugated cortisol (200–1000 ng∙mL−1). Urine of herring and plaice had particularly high levels of conjugated cortisol (ca. 5 μg∙mL−1). Uncontaminated seminal fluid from herring, but not from plaice, also had high levels of conjugated cortisol (ca. 2 μg∙mL−1). Urine and plasma, but not seminal fluid, of herring had elevated levels of conjugated 17α,20β-dihydroxy-4-pregnen-3-one. Urine, but not plasma or seminal fluid, of male plaice had elevated levels of 17α,20α -dihydroxy-4-pregnen-3-one and 3α,17α,21-trihydroxy-5β-pregnan-20-one. It would appear that fish urine is a rich source of conjugated steroids and that care must be taken, when collecting milt for pheromone studies, to avoid urine contamination.

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6

Grandgirard, André, Stéphanie Cabaret, Lucy Martine, and Olivier Berdeaux. "New Internal Standard for Quantitative Determination of Oxyphytosterols by Gas Chromatography." Journal of AOAC INTERNATIONAL 87, no. 2 (2004): 481–84. http://dx.doi.org/10.1093/jaoac/87.2.481.

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Abstract A study was conducted to develop a new internal standard for the quantitative determination of oxyphytosterols. Tests on 5α-androsten-3β,17β-diol; 5α-androstan-3β, 17β-diol; 5-pregnen-3β,20α-diol; and 5α-pregnan-3β,20β-diolshowed that these compounds were not fully adequate. However, the compound 3β,22-dihydroxy-20-homo-5-pregnene, synthesized in 4 steps, resulted in a promising internal standard, with a molecule similar to hydroxysterols; retention time as trimethylsilyl in gas chromatography comprised between 5α-cholestane and 7α-hydroxycholesterol; clear mass spectrum in electronic impact mass spectrometry, with several intense ions suitable for selected ion monitoring-mass spectrometry. Further studies are necessary to observe the behavior of these compounds during the entire analytical procedure.

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7

Choudhary, Muhammad I., Syed G. Musharraf, Rahat A. Ali, Muhammad Atif та Atta-ur Rahman. "Microbial Transformation of Antifertility Agents, Norethisterone and 17α-Ethynylestradiol". Zeitschrift für Naturforschung B 59, № 3 (2004): 319–23. http://dx.doi.org/10.1515/znb-2004-0314.

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The microbial transformation of oral contraceptive norethisterone (1) by Cephalosporium aphidicola afforded an oxidized metabolite, 17α-ethynylestradiol (2), while the microbial transformation of 2 by Cunninghamella elegans yielded several metabolites, 19-nor-17α-pregna-1,3,5 (10)- trien-20-yne-3,4,17β -triol (3), 19-nor-17α-pregna-1,3,5 (10)-trien-20-yne-3,7α,17β -triol (4), 19- nor-17α-pregna-1,3,5 (10)-trien-20-yne-3,11α,17β -triol (5), 19-nor-17α-pregna-1,3,5 (10)-trien-20- yne-3,6β ,17β -triol (6) and 19-nor-17α-pregna-1,3,5 (10)-trien-20-yne-3,17β -diol-6β -methoxy (7). Metabolite 7 was found to be a new compound. These metabolites were structurally characterized on the basis of spectroscopic techniques

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8

Yousuf, S., S. G. Musharraf, N. Iqbal, A. Adhikari та M. I. Choudhary. "3α-Dimethylamino-20-(N-methylacetamido)pregn-5-ene". Acta Crystallographica Section E Structure Reports Online 67, № 11 (2011): o2918. http://dx.doi.org/10.1107/s160053681103964x.

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9

Oliver, James E., та William R. Lusby. "Glucosylations of pregn-5-ene-3β,20R-diol". Steroids 52, № 3 (1988): 265–78. http://dx.doi.org/10.1016/0039-128x(88)90008-6.

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10

Nahar, Lutfun, Satyajit D. Sarker, and Alan B. Turner. "Synthesis of Pregnenolone and Methyl Lithocholate Oxalate Derivatives." Natural Product Communications 3, no. 1 (2008): 1934578X0800300. http://dx.doi.org/10.1177/1934578x0800300106.

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Five new steroidal oxalate derivatives, oxalic acid (pregn-5-en-20-one)-3β-yl ethyl ester (2), oxalic acid mono (pregn-5-en-20-one)-3β-yl ester (3), chloro-oxo-acetic acid (5β-cholan-24-oic acid methyl ester)-3α-yl ester (5), oxalic acid mono (5β-cholan-24-oic acid methyl ester)-3α-yl ester (6) and oxalic acid (5β-cholan-24-oic acid methyl ester)-3α-yl ethyl ester (7) were synthesized, respectively, from pregnenolone (1) and methyl lithocholate (4) using excess oxalyl chloride.

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11

Gröndal, Staffan, та Tore Curstedt. "Steroid profile in serum: increased levels of sulphated pregnenolone and pregn-5-ene-3β,20α-diol in patients with adrenocortical carcinoma". Acta Endocrinologica 124, № 4 (1991): 381–85. http://dx.doi.org/10.1530/acta.0.1240381.

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Abstract. A serum steroid profile was determined in 11 patients with adrenocortical carcinoma, 5 with adrenocortical adenoma and 10 healthy controls. Seven of the patients with carcinoma had different forms of endocrine symptoms, and of those with adenoma 3 had Cushing's syndrome and 2 primary hyperaldosteronism. Sulphated steroids dominated in serum from both patients and controls, whereas the levels of free and glucuronated steroids were low. All patients with adrenocortical carcinoma had increased levels of sulphated pregn-5-ene-3β-ol-20-one (pregnenolone) and pregn-5-ene-3β,20α-diol compared with healthy controls and patients with adrenocortical adenoma. Serum levels of 11-deoxycortisol and/or its glucuronated metabolite tetrahydro-11-deoxycortisol were clearly elevated in 8 of the patients with carcinoma. The results are in agreement with those previously found for conjugated urinary steroids in patients with adrenocortical carcinoma. Thus, an impaired function or deficiency of 3β-hydroxysteroid dehydrogenase/Δ5-4 isomerase and in some cases also of 11β-hydroxylase could explain the findings. The sulphated pregnenolone and/or pregn-5-ene-3β,20α-diol, possibly together with free11-deoxycortisol seem to be useful for preoperative discrimination between malignant and benign adrenocortical tumours.

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12

Purushothaman, K. K., A. Sarada, and A. Saraswathy. "Chemical constituents of Lansiumanamallayanum Bedd." Canadian Journal of Chemistry 65, no. 1 (1987): 150–53. http://dx.doi.org/10.1139/v87-023.

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Several triterpenoids and steroids have been isolated from Lansiumanamallayanum Bedd. The leaves yielded an unknown triterpene lansitriol and four new steroids, lansisterone E1, lansisterone Z2, lansisterol B, and lansisterol A 3. From the bark, a new triterpene lactone designated as lansilactone 4 was isolated. Structures for compounds 1, 2, 3, and 4 have been proposed as 3β,4β-dihydroxy-17(20)-trans 5α-pregna-16-one; 3β,4β-dihydroxy-17(20)-trans 5α-pregna-16-one; 24-methylene 3β,4β,7β, 20-tetrahydroxy cholest-5-ene, and 25,26,27-lanostane trisnorlactone.

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13

Petrera, Erina, Maria Joselevich, Alberto Ghini, Gerardo Burton, and Celia E. Coto. "Antiherpes Virus Activities of New 6–19 Carbon-Bridged Steroids and Some Synthetic Precursors." Antiviral Chemistry and Chemotherapy 14, no. 5 (2003): 243–48. http://dx.doi.org/10.1177/095632020301400503.

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Three synthetic 6,19-carbon bridged steroids: 3β,20β-diacetyloxy-5α-chloro-19a(R)-hydroxy-6,19-methanopregnane, 3β,20β-diacetyloxy-5α-chloro-6,19-methanopregnane, 6,19-methanopregn-4-ene-3,20-dione and four synthetic precursors: 3β,20β-diacetyloxy-19-hydroxypregn-5-ene, 3β,20β-diacetyloxy-pregn-5-en-19-al, 3β,20β-diacetyloxy-19(E)-(methoxymethylidene)-pregn-5-ene and 20β-acetyloxy-3β-hydroxy-19(E)-(methoxymethylidene)-pregn-5-ene were tested against herpes virus replication in cell cultures. Several compounds were cytotoxic for stationary cells. Antiviral studies performed with all compounds against HSV-1 indicated a dose-dependent virus susceptibility with selectivity indexes (SI) values in the range 1.7–183.2. Selected compounds were also tested against HSV-2 and the SI values obtained were in the range of 31–273. Attempts to reveal the step of virus multiplication affected by pregnanes were performed with one compound. HSV-1 virus incubation with the compound did not alter the ability of virus particles to infect cells; moreover, neither virus adsorption nor penetration appeared to be affected. The drug must be present during at least the first 7 h of the virus cycle to inhibit more than 90% of virus production. All these results suggest that these novel molecules interfere with an intracellular step of virus multiplication, thus behaving like true antivirals.

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14

Warthen, J. D., R. M. Waters та J. E. Oliver. "1H NMR chemical shift studies of pregn-5-ene-3β,20(R)-diol and pregn-5-ene-3β-ol,20-one d-glucopyranoside derivatives". Spectrochimica Acta Part A: Molecular Spectroscopy 46, № 3 (1990): 369–75. http://dx.doi.org/10.1016/0584-8539(90)80107-a.

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15

Kasal, Alexander, Jenny Pokorná та Jaroslav Zajíček. "3β,11α,17-Trihydroxy-5-pregnen-20-one 11-hemisuccinate as a haptene for RIA of "17α-hydroxypregnenolone"". Collection of Czechoslovak Chemical Communications 56, № 6 (1991): 1340–47. http://dx.doi.org/10.1135/cccc19911340.

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6β,17-Dihydroxy-3α,5-cyclo-5α-pregnan-20-one (VII) and 17-hydroxy-6β-methoxy-3α,5-cyclo-5α-pregnan-20-one (IX) were hydroxylated into the position 11α using Rhizopus nigricans fungi culture, and then selectively converted into haptene XIII for the RIA determination of 3β,17-dihydroxypregn-5-en-20-one (IV).

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16

Kapras, Vojtěch, Eva Šťastná, Hana Chodounská, Vladimír Pouzar, and Zdena Krištofíková. "Preparation of steroid sulfamates and their interaction with GABAA receptor." Collection of Czechoslovak Chemical Communications 74, no. 4 (2009): 643–50. http://dx.doi.org/10.1135/cccc2008187.

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Sulfamoyl chloride was used for the preparation of 3α- and 3β-sulfamates of steroids: 20-oxo-5α-pregnan-3α-yl sulfamate (4), 20-oxo-5α-pregnan-3β-yl sulfamate (5), 20-oxo-5β-pregnan-3α-yl sulfamate (7), and 20-oxo-5β-pregnan-3β-yl sulfamate (9) from the corresponding 3α- and 3β-alcohols. Sulfur trioxide–pyridine complex was employed for the preparation of 20-oxo-5α-pregnan-3α-yl pyridinium sulfate (10). The specific steroid binding was detected by the decrease of the specific [35S]-tert-butylbicyclo[2.2.2]phosphorothionate binding after application of the tested compounds.

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17

Back, Thomas G., Joseph H. L. Chau, Brian P. Dyck та Patricia L. Gladstone. "The synthesis of some novel N-chloro-Δ1-4-azasteroids by efficient N-chlorination of azasteroid lactams with trichloroisocyanuric acid". Canadian Journal of Chemistry 69, № 9 (1991): 1482–86. http://dx.doi.org/10.1139/v91-219.

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The preparation of N-chloro-Δ1-4-azasteroids 2a–2c from lactams 1a–1c was achieved conveniently and in high yield with trichloroisocyanuric acid. The treatment of 20β-hydroxy-4-aza-5α-pregn-1-en-3-one (1d) with this reagent produced the less stable N-chloro compound 2d, which reacted further to afford 4-aza-5α-pregn-1-en-3,20-dione (4) as the principal product. The similar chlorination of 4-azacholest-5-en-3-one (5) occurred at C-6, giving 6-chloro-4-azacholest-5-en-3-one (6). Photolysis of N-chloro-4-aza-5α-cholest-1-en-3-one (2a) in methanol produced the transient N-acyl imine 7, which was trapped by the solvent to afford 5-methoxy-4-azacholest-1-en-3-one (8), along with 4-azacholesta-1,5-dien-3-one (9) and its 6-chloro derivative 10. Key words: N-chloroazasteroid, Δ1-4-azasteroid, N-chloro-Δ1-4-azasteroid, trichloroisocyanuric acid, N-chlorination.

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18

Pozo, Oscar J., Josep Marcos, Olha Khymenets, et al. "SULFATION PATHWAYS: Alternate steroid sulfation pathways targeted by LC–MS/MS analysis of disulfates: application to prenatal diagnosis of steroid synthesis disorders." Journal of Molecular Endocrinology 61, no. 2 (2018): M1—M12. http://dx.doi.org/10.1530/jme-17-0286.

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The steroid disulfates (akabis-sulfates) are a significant but minor fraction of the urinary steroid metabolome that have not been widely studied because major components are not hydrolyzed by the commercial sulfatases commonly used in steroid metabolomics. In early studies, conjugate fractionation followed by hydrolysis using acidified solvent (solvolysis) was used for the indirect detection of this fraction by GC–MS. This paper describes the application of a specific LC–MS/MS method for the direct identification of disulfates in urine, and their use as markers for the prenatal diagnosis of disorders causing reduced estriol production: STSD (steroid sulfatase deficiency), SLOS (Smith-Lemli-Opitz syndrome) and PORD (P450 oxidoreductase deficiency). Disulfates were detected by monitoring a constant ion loss (CIL) from the molecular di-anion. While focused on disulfates, our methodology included an analysis of intact steroid glucuronides and monosulfates because steroidogenic disorder diagnosis usually requires an examination of the complete steroid profile. In the disorders studied, a few individual steroids (as disulfates) were found particularly informative: pregn-5-ene-3β,20S-diol, pregn-5-ene-3β,21-diol (STSD, neonatal PORD) and 5α-pregnane-3β,20S-diol (pregnancy PORD). Authentic steroid disulfates were synthesized for use in this study as aid to characterization. Tentative identification of 5ξ-pregn-7-ene-3ξ,20S-diol and 5ξ-pregn-7-ene-3ξ,17,20S-triol disulfates was also obtained in samples from SLOS affected pregnancies. Seven ratios between the detected metabolites were applied to distinguish the three selected disorders from control samples. Our results show the potential of the direct detection of steroid conjugates in the diagnosis of pathologies related with steroid biosynthesis.

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19

Deb, Subrata, Steven Pham, Dong-Sheng Ming, et al. "Characterization of Precursor-Dependent Steroidogenesis in Human Prostate Cancer Models." Cancers 10, no. 10 (2018): 343. http://dx.doi.org/10.3390/cancers10100343.

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Castration-resistant prostate tumors acquire the independent capacity to generate androgens by upregulating steroidogenic enzymes or using steroid precursors produced by the adrenal glands for continued growth and sustainability. The formation of steroids was measured by liquid chromatography-mass spectrometry in LNCaP and 22Rv1 prostate cancer cells, and in human prostate tissues, following incubation with steroid precursors (22-OH-cholesterol, pregnenolone, 17-OH-pregnenolone, progesterone, 17-OH-progesterone). Pregnenolone, progesterone, 17-OH-pregnenolone, and 17-OH-progesterone increased C21 steroid (5-pregnan-3,20-dione, 5-pregnan-3,17-diol-20-one, 5-pregnan-3-ol-20-one) formation in the backdoor pathway, and demonstrated a trend of stimulating dihydroepiandrosterone or its precursors in the backdoor pathway in LNCaP and 22Rv1 cells. The precursors differentially affected steroidogenic enzyme messenger RNA (mRNA) expressions in the cell lines. The steroidogenesis following incubation of human prostate tissue with 17-OH-pregnenolone and progesterone produced trends similar to those observed in cell lines. Interestingly, the formation of C21 steroids from classical pathway was not stimulated but backdoor pathway steroids (e.g., 5-pregnan-3,20-dione, 5-pregnan-3-ol-20-one) were elevated following incubations with prostate tissues. Overall, C21 steroids were predominantly formed in the classical as well as backdoor pathways, and steroid precursors induced a diversion of steroidogenesis to the backdoor pathway in both cell lines and human prostate tissue, and influenced adaptive steroidogenesis to form C21 steroids.

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20

Huo, Shao-Jie, Ji-Chun Wu, Xi-Chen He, Qi-Yun Wu та Jiang Du. "Crystal structure of 3β-methoxy-20α-dimethylamino-pregn-5-ene, C24H41NO". Zeitschrift für Kristallographie - New Crystal Structures 233, № 6 (2018): 1057–58. http://dx.doi.org/10.1515/ncrs-2018-0168.

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21

Chien, Nguyen Quyet, та Günter Adam. "1α,3β-Dihydroxy-pregn-5-en-20-on durch Witanolid-Seitenkettenabbau". Zeitschrift für Chemie 24, № 12 (2010): 439. http://dx.doi.org/10.1002/zfch.19840241207.

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22

Bhat, Z. A., M. Ali, S. H. Ansari, and K. J. Naquvi. "PHYTOCHEMICAL INVESTIGATION OF AERIAL PARTS OF SWERTIA TETRAGONA EDGEW." INDIAN DRUGS 49, no. 05 (2012): 35–38. http://dx.doi.org/10.53879/id.49.05.p0035.

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Swertia tetragona Edgew (Gentianaceae) is a Himalayan herb used as a substitute for S. chirayita.Phytochemical investigation of its aerial parts yielded pregn-4-en-3?-ol, 1-methoxy-4, 5-dihydroxy-7-methyl xanthone and stigmasterol characterized on the basis of spectral data analysis.

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23

Stuhlemmer, Ursel, Werner Haussmann, Frank Milek, Wolfgang Kreis та Ernst Reinhard. "3 α-Hydroxysteroid-5β-oxidoreductase in Tissue Cultures of Digitalis lanata". Zeitschrift für Naturforschung C 48, № 9-10 (1993): 713–21. http://dx.doi.org/10.1515/znc-1993-9-1006.

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Abstract Putative intermediates of cardenolide biosynthesis, namely progesterone, pregnenolone, 5β-pregnane-3,20-dione or 5β-pregnan-3β-ol-20-one, were administered to light- or darkgrown shoot cultures of Digitalis lanata. The unsaturated com pounds were reduced to their respective 5 a-pregnanes, 5β-pregnane-3,20-dione was reduced to 5β-pregnan-3α-ol-20-one and 5β-pregnan-3β-ol-20-one was isomerized to the respective 3α-pregnane. Suspension cultures of Digitalis lanata, on the other hand, accumulated both the 3α- and the 3β-isom er of 5β-pregnan-3-ol-20-one when incubated in the presence of 5β-pregnane- 3.20-dione. When 5β-pregnan-3α-ol-20-one was administered the cultured cells accumulated large amounts of the 3β-isomer together with small amounts of 5β-pregnane-3,20-dione, which may be regarded as an intermediate during the isomerization reaction. Cell-free, buffered extracts from light-grown shoots were shown to reduce 5β-pregnane- 3.20-dione almost exclusively to 5β-pregnan-3α-ol-20-one when 0.05 m MgCl2 were present in the incubation mixture. Under these conditions the formation of 5β-pregnan-3β-ol-20-one was inhibited. The enzyme activity could be recovered from m em brane-free supernatants. Optimum enzyme activity occurred at pH 7.0 and 42 °C. The energy of activation was 56.2 kJ/mol and the enzyme reaction was found to be NADPH -dependent. SH reagents were essential for enzyme activity. The enzyme seems to be specific for 5β-pregnan-3-ones since neither 5 a-pregnane-3-ones nor Δ4/Δ5-pregnenes were reduced. The NADPH : 5β-pregnane 3α-hydroxysteroid-5β-oxidoreductase described here may play a role in the regulation of cardenolide biosynthesis by removing precursors, such as 5β-pregnane-3,20-dione, from the pathway

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24

Radhakrishnan, R., M. A. Viswamitra, K. K. Bhutani та R. M. Vaid. "The structure of 3β,20α-bis(dimethylamino)pregn-5-en-18-ol". Acta Crystallographica Section C Crystal Structure Communications 44, № 10 (1988): 1820–23. http://dx.doi.org/10.1107/s0108270188006808.

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25

Galdecki, Z., P. Grochulski, Z. Wawrzak, William L. Duax, Phyllis Strong та Albert Segaloff. "Structure determination of 3β,17-dihydroxy-17α-pregn-5-ene-20-one". Steroids 45, № 3-4 (1985): 289–96. http://dx.doi.org/10.1016/0039-128x(85)90077-7.

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26

Polman, Jiří, та Alexander Kasal. "The synthesis of 5-methyl-19-nor-5β-pregna-9,16-diene-3,20-dione, 5-methyl-19-nor-5β-pregna-9,10-diene-3,6,20-trione and their analogues with annellated E ring". Collection of Czechoslovak Chemical Communications 56, № 12 (1991): 2892–905. http://dx.doi.org/10.1135/cccc19912892.

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The synthesis of compounds VII, XVII, XXXIV and XXXVII is described, in which biological activity is assumed. The key steps of their preparation are the dehalogenation of compound XVIII and radicalic deoxygenation of the 6β-hydroxy group in compound XXX, which take place without skeletal rearrangements.

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Sethi, Arun, Akriti Bhatia, Ranvijay Pratap Singh, and Atul Srivastava. "Synthesis and Evaluation of Some Novel Pregnane Derivatives as Anti-Hyperlipidemic and Anti-Oxidant Agents." Letters in Organic Chemistry 16, no. 1 (2018): 40–49. http://dx.doi.org/10.2174/1570178615666180806123719.

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In the present paper, synthesis of few novel pregnane derivatives and their evaluation as potential anti-hyperlipidemic and anti-oxidant agents has been reported. The synthesis of 3&#946;-hydroxy- 16&#945;-methoxy pregn-5-en-20-one (4) was achieved by reaction of 3&#946;-hydroxy-5,16-pregnadiene-20-one (3) with KOH/MeOH under reflux. Compound 4 on treatment with succinic and phthalic anhydride afforded compound 6 and 7, respectively. The reaction of the C-20-oxime-pregnadiene (8) with 1,5- dibromohexane yielded 20-(O-6-bromo hexyl)-oximino-3&#946;-hydroxy-pregn-5, 16-diene (9). A novel heterocyclic derivative 3&#946;-hydroxy-androst-5-en [17,16-c]-2′-methyl-7′ bromo-3′,4′-dihydro quinoline (16) was synthesized by reaction of 3 with 3-bromoaniline. However, attempted synthesis of other heterocyclic derivatives by reaction of (3) with other halogenated amine led to Aza-Michael addition products (10-14). The synthesized compounds were also evaluated for their anti-hyperlipidemic and anti-oxidant activities. Compounds 6 and 14 were found to exhibit more lipid lowering and antioxidant activities in comparison to other compounds.

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Visbal, Gonzalo, Alvaro Alvarez, Belisario Moreno та Gioconda San-Blas. "S-Adenosyl-l-Methionine Inhibitors Δ24-Sterol Methyltransferase and Δ24(28)-Sterol Methylreductase as Possible Agents against Paracoccidioides brasiliensis". Antimicrobial Agents and Chemotherapy 47, № 9 (2003): 2966–70. http://dx.doi.org/10.1128/aac.47.9.2966-2970.2003.

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ABSTRACT We studied the antiproliferative effects of three azasterol analogs [piperidyl-2-yl-5α-pregnan-3β,20(R)-diol (AZA-1), 22-piperidin-2-yl-pregnan-22(S),3β-diol (AZA-2), and 22-piperidin-3-yl-pregnan-22(S),3β-diol (AZA-3)] and their effects on the lipid composition of the pathogenic yeastlike phase of the dimorphic fungus Paracoccidioides brasiliensis. Inhibition was 100% for AZA-1 at 5 μM, 62% for AZA-2 at 10 μM, and 100% for AZA-3 at 0.5 μM. The analogs inhibited different stages of the sterol biosynthesis pathway.

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29

Decréau, Richard A., and Charles M. Marson. "Preparation of 3,17‐ and 3,20‐Difluoro‐Derivatives of the Androst‐5‐ene and Pregn‐5‐ene Series." Synthetic Communications 34, no. 23 (2004): 4369–85. http://dx.doi.org/10.1081/scc-200039449.

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30

Turuta, A. M., N. E. Voishvillo, A. V. Kamernitskii, N. V. Dzhlantiashvili, and A. A. Korobov. "Transformation of 5?-H-pregn-16-en-3?-ol-20-one into pregn-4-ene-9?,16?,17?-triol-3,20-dione 16,17-acetonide." Bulletin of the Russian Academy of Sciences Division of Chemical Science 41, no. 8 (1992): 1482–84. http://dx.doi.org/10.1007/bf00864351.

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31

Baranovsky, A. V., and R. P. Litvinovskaya. "1H and 13C NMR Spectral Characteristics of 15-Substituted Pregn-5-Ene and Androst-5-Ene Steroid Compounds." Journal of Applied Spectroscopy 86, no. 5 (2019): 867–76. http://dx.doi.org/10.1007/s10812-019-00908-z.

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32

Duax, W. L., J. F. Griffin, P. D. Strong та Y. Guan. "Structure of 3β-hydroxy-16α-methyl-5-pregnen-20-one". Acta Crystallographica Section C Crystal Structure Communications 45, № 9 (1989): 1433–35. http://dx.doi.org/10.1107/s0108270189004488.

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33

Holland, Herbert L., Ronald W. Ninniss, and Frances M. Brown. "Stereochemistry of hydrogen loss during C-21 dehydroxylation of tetrahydrodeoxycorticosterone by Eubacteriumlentum." Canadian Journal of Chemistry 67, no. 10 (1989): 1590–95. http://dx.doi.org/10.1139/v89-242.

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The loss of hydrogen from the C-21 position of 5β-pregnane-3α,21-diol-20-one (tetrahydrodeoxycorticosterone, THDOC) during reductive removal of the 21-hydroxy group by the anaerobic bacterium Eubacteriumlentum has been shown to be selective for the pro-S position by the use of THDOC labelled with deuterium at the C-21 pro-S and C-21 pro-R positions. The labelled substrates were obtained by using the bacterium Clostridiumparaputrificum to reduce chemically prepared C-21 labelled samples of pregn-4-en-21-ol-3,20-dione (deoxycorticosterone, DOC) at C-3 and C-4 (5). The stereochemistry of deuterium label introduced by chemical means at C-21 of DOC was determined by comparison with a sample of 21-(R)-DOC-21-d1 produced by reduction of the corresponding aldehyde pregn-4-en-21-al-3,20-dione, 21-d by the enzyme 21-hydroxysteroid NAD oxidoreductase from beef liver. Keywords: Eubacterium, Clostridium, steroids, tetrahydrodeoxycorticosteroids.

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34

Kasal, Alexander, Jiří Polman та Miloš Buděšínský. "Hydrogenation of a Tetrasubstituted Double Bond: Synthesis of 5-Methyl-19-nor-5β-pregnanes". Collection of Czechoslovak Chemical Communications 63, № 10 (1998): 1549–63. http://dx.doi.org/10.1135/cccc19981549.

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Reduction of C=C and/or C=O bonds in 5-methyl-19-nor-5β-pregn-9-ene-3,20-dione (1) leads to saturated and unsaturated ketones and hydroxy ketones. The C=C reduction affords mainly 9β,10β and 9α,10β dihydro products. Reaction conditions of partial esterification, hydrolysis and oxidation were elaborated. Several analogues were prepared for the testing of gestagenic and neurosteroidal activities.

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35

Pouzar, Vladimír, Tereza Slavíková, and Ivan Černý. "Preparation of 7-[O-(Carboxymethyl)oxime] Derivatives of Dehydroepiandrosterone and Pregnenolone." Collection of Czechoslovak Chemical Communications 61, no. 3 (1996): 404–12. http://dx.doi.org/10.1135/cccc19960404.

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Novel simple syntheses of 7-(O-carboxymethyloxime) derivatives of 3β-hydroxyandrost-5-en-17-one (dehydroepiandrosterone) and of 3β-hydroxypregn-5-en-20-one (pregnenolone) are reported. In the first one, 17-oxoandrost-5-en-3β-yl acetate was oxidized to give the 7,17-dione which was then selectively reduced in the position 17. Oximation, reoxidation, and deacetylation yielded the desired oxime. The second synthesis started with (20R)-pregn-5-ene-3β,20-diol 3-acetate which was converted to the 20-nitrate, oxidized to the C-7 ketone, oximated, partially deprotected in position 20, reoxidized, and deacetylated. Both the 7-(O-carboxymethyloxime) derivatives have been devised as immunoassay components.

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36

Kasal, Alexander. "Epalons: Synthesis of 7-Norallopregnanolone." Collection of Czechoslovak Chemical Communications 64, no. 9 (1999): 1471–78. http://dx.doi.org/10.1135/cccc19991471.

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The title compound 2 was prepared from (20R)-pregn-5-ene-3β,20-diyl 3-acetate 20-benzoate (3) via (20R)-3β-acetoxy-20-benzoyloxy-5-oxo-5,6-secopregnan-6-oic acid (5) and (20R)-3β-acetoxy-20-benzoyloxy-7-nor-5β,6α-pregnane-6,5-carbolactone (6). An intermediate 7-norpregn-5-ene derivative - (20R)-7-norpregn-5-ene-3β,20-diyl 3-acetate 20-benzoate (7) - was hydrogenated using diimide in statu nascendi. The inversion of configuration at carbon C-3 was carried out via (20R)-7-nor-5α-pregnane-3β,20-diyl 3-tosylate 20-benzoate (12) and (20R)-7-nor-5α-pregnane-3α,20-diyl 20-benzoate 3-formate (13).

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37

Deb, Subrata, Mei Yieng Chin, Steven Pham, et al. "Steroidogenesis in Peripheral and Transition Zones of Human Prostate Cancer Tissue." International Journal of Molecular Sciences 22, no. 2 (2021): 487. http://dx.doi.org/10.3390/ijms22020487.

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The peripheral zone (PZ) and transition zone (TZ) represent about 70% of the human prostate gland with each zone having differential ability to develop prostate cancer. Androgens and their receptor are the primary driving cause of prostate cancer growth and eventually castration-resistant prostate cancer (CRPC). De novo steroidogenesis has been identified as a key mechanism that develops during CRPC. Currently, there is very limited information available on human prostate tissue steroidogenesis. The purpose of the present study was to investigate steroid metabolism in human prostate cancer tissues with comparison between PZ and TZ. Human prostate cancer tumors were procured from the patients who underwent radical prostatectomy without any neoadjuvant therapy. Human prostate homogenates were used to quantify steroid levels intrinsically present in the tissues as well as formed after incubation with 2 µg/mL of 17-hydroxypregnenolone (17-OH-pregnenolone) or progesterone. A Waters Acquity ultraperformance liquid chromatography coupled to a Quattro Premier XE tandem quadrupole mass spectrometer using a C18 column was used to measure thirteen steroids from the classical and backdoor steroidogenesis pathways. The intrinsic prostate tissue steroid levels were similar between PZ and TZ with dehydroepiandrosterone (DHEA), dihydrotestosterone (DHT), pregnenolone and 17-OH-pregnenolone levels higher than the other steroids measured. Interestingly, 5-pregnan-3,20-dione, 5-pregnan-3-ol-20-one, and 5-pregnan-17-ol-3,20-dione formation was significantly higher in both the zones of prostate tissues, whereas, androstenedione, testosterone, DHT, and progesterone levels were significantly lower after 60 min incubation compared to the 0 min control incubations. The incubations with progesterone had a similar outcome with 5-pregnan-3,20-dione and 5-pregnan-3-ol-20-one levels were elevated and the levels of DHT were lower in both PZ and TZ tissues. The net changes in steroid formation after the incubation were more observable with 17-OH-pregnenolone than with progesterone. In our knowledge, this is the first report of comprehensive analyses of intrinsic prostate tissue steroids and precursor-driven steroid metabolism using a sensitive liquid chromatography-mass spectrometry assay. In summary, the PZ and TZ of human prostate exhibited similar steroidogenic ability with distinction in the manner each zone utilizes the steroid precursors to divert the activity towards backdoor pathway through a complex matrix of steroidogenic mechanisms.

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38

Popova, Pavlinka, Yancho Zarev, Rositsa Mihaylova, Georgi Momekov, and Iliana Ionkova. "Antiproliferative activity of extract from in vitro callus cultures of Astragalus vesicarius ssp. carniolicus (A. Kern.) Chater." Pharmacia 68, no. 1 (2021): 217–21. http://dx.doi.org/10.3897/pharmacia.68.e63421.

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Five isoflavonoids, i.e. 5-hydroxy-7-methoxy-2’, 5’-dihydroxyisoflavone (AV4), 5, 7-dihydroxy-4’-methoxyisoflavone (AV6), 7-methoxy-5-hydroxy-4’-methoxy-2’-hydroxyisoflavone (AV7), 8-pregnyl genistein (AV9), 5,7-dihydroxy-8-pregnyl-4’-methoxy-2’-hydroxyisoflavone (AV10) and one coumarochromone – sophorophenolone (AV8) were isolated from EtOAc of in vitro callus cultures of Astragalus vesicarius ssp. carniolicus, after enzymatic hydrolysis with β-glucosidase. Their structures were tentatively elucidated by spectroscopic mean (1H NMR and HR-ESI-MS spectra). Antiproliferative activity of EtOAc extract and isolated aglycones against chemosensitive human promyelocyte cell line HL-60 and its multidrug-resistant variant HL-60/Dox was assessed in vitro. Despite the strong activity of EtOAc (IC50 8.8 µg/mL (HL-6, 72 h) to 11.8 µg/mL (HL-60/Dox, 72 h)), prenylated compound AV9 showed also antiproliferative activity – 36.1 µg/mL (HL-60 and HL-60/Dox, 72 h).

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39

Popova, Pavlinka, Yancho Zarev, Rositsa Mihaylova, Georgi Momekov, and Iliana Ionkova. "Antiproliferative activity of extract from in vitro callus cultures of Astragalus vesicarius ssp. carniolicus (A. Kern.) Chater." Pharmacia 68, no. (1) (2021): 217–21. https://doi.org/10.3897/pharmacia.68.e63421.

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Five isoflavonoids, i.e. 5-hydroxy-7-methoxy-2', 5'-dihydroxyisoflavone (AV4), 5, 7-dihydroxy-4'-methoxyisoflavone (AV6), 7-methoxy-5-hydroxy-4'-methoxy-2'-hydroxyisoflavone (AV7), 8-pregnyl genistein (AV9), 5,7-dihydroxy-8-pregnyl-4'-methoxy-2'-hydroxyisoflavone (AV10) and one coumarochromone – sophorophenolone (AV8) were isolated from EtOAc of in vitro callus cultures of Astragalus vesicarius ssp. carniolicus, after enzymatic hydrolysis with β-glucosidase. Their structures were tentatively elucidated by spectroscopic mean (<sup>1</sup>H NMR and HR-ESI-MS spectra). Antiproliferative activity of EtOAc extract and isolated aglycones against chemosensitive human promyelocyte cell line HL-60 and its multidrug-resistant variant HL-60/Dox was assessed in vitro. Despite the strong activity of EtOAc (IC<sub>50</sub> 8.8 µg/mL (HL-6, 72 h) to 11.8 µg/mL (HL-60/Dox, 72 h)), prenylated compound AV9 showed also antiproliferative activity – 36.1 µg/mL (HL-60 and HL-60/Dox, 72 h).

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40

Pouzar, Vladimír, Lenka Kárászová та Miroslav Havel. "Preparation of 21-methoxycarbonyl-21-methylene-5-pregnen-3β-ol derivatives". Collection of Czechoslovak Chemical Communications 52, № 11 (1987): 2735–43. http://dx.doi.org/10.1135/cccc19872735.

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Reaction of 3β-methoxymethoxy-21-nor-5-pregnen-20-ol p-toluenesulfonate (II) with sodium dimethyl malonate afforded dimethyl 3β-methoxymethoxy-5-pregnene-21,21-dicarboxylate (III). Partial hydrolysis of III, followed by reaction with formaldehyde and diethylamine, gave methyl 3β-methoxymethoxy-21-methylene-5-pregnene-21-carboxylate (XVI) which was further transformed into hemisuccinate XIX.

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41

Lisgarten, David R., John N. Lisgarten, and Rex A. Palmer. "Crystal structure and charge distribution for 20 oximino-5?-pregn-16-eno[3, 4,-c]-1?2?5?-oxadiazole (HS998)." Journal of Crystallographic and Spectroscopic Research 23, no. 4 (1993): 273–78. http://dx.doi.org/10.1007/bf01263586.

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42

Shestak, O. P., V. L. Novikov, A. V. Skorova, and A. V. Kamernitskii. "Novel skeletal rearrangement of 3?-acetoxy-5?-pregna-14,16-dien-20-one to 3?-acetoxy-17-acetyl-5?-etiojerva-12,14,16-triene." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 37, no. 6 (1988): 1230–32. http://dx.doi.org/10.1007/bf00961938.

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43

Stulov, S. V., N. O. Dugin, M. S. Zharkova, et al. "Interaction of novel oxazoline derivatives of 17(20)e-pregna-5,17(20)-diene with cytochrome P450 17A1." Biomeditsinskaya Khimiya 62, no. 1 (2016): 38–44. http://dx.doi.org/10.18097/pbmc20166201038.

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In order to find novel inhibitors of 17a-hydroxylase-17,20-lyase (cytochrome P450 17A1, CYP17A1), a key enzyme of biosynthesis of androgens, molecular docking of six new oxazoline-containing derivatives 17(20)E-pregna-5,17(20)-diene has been carried out to the active site of the crystal structure of CYP17A1 (pdb 3ruk). Results of this study indicate that: 1) complex formation of docked compounds with CYP17A1 causes their isomerization in energetically less favorable 17(20)Z-isomer; 2) the localization of the steroid moiety of all compounds in the active site is basically the same; 3) the structure of the oxazoline moiety significantly influences its position relative to heme as well as the energy of complex formation; 4) coordination of the nitrogen atom of the oxazoline moiety and the heme iron is only possible in the 17(20)Z-conformation with anti oriented double bonds 17(20), and C=N; 5) the presence of two substituents at C4' of the oxazoline moiety significantly impairs ligand binding; 6) oxazoline - and benzoxazole-containing derivatives 17(20)E-pregna-5,17(20)-diene can effectively inhibit the catalytic activity CYP17A1 and may be of interest as a basis for the development of new drugs for the treatment of androgen-dependent cancer.

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44

ITOH, SHINJI, and ITSUO YOSHIZAWA. "A Synthetic Method of 5β-Pregn-20-en-3α-ol from Lithocholic Acid." YAKUGAKU ZASSHI 105, no. 5 (1985): 507–11. http://dx.doi.org/10.1248/yakushi1947.105.5_507.

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45

Kamperdick, Christine, Tran Van Sung, Trinh Thi Thuy, Mai Van Tri та Günter Adam. "(20R)-O-(3)-α-l-arabinopyranosyl-pregn-5-en-3β,20-diol from Brucea javanica". Phytochemistry 38, № 3 (1995): 699–701. http://dx.doi.org/10.1016/0031-9422(94)00737-e.

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46

Lindeman, S. V., A. M. Turuta, Yu T. Struchkov, and A. V. Kamernitskii. "The structure of 16, 17?-epoxy-17?-pregn-5-en-3?-ol-20-one monohydrate." Russian Chemical Bulletin 42, no. 2 (1993): 365–70. http://dx.doi.org/10.1007/bf00697098.

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47

Ripperger, Helmut, та Klaus Schreiber. "Anlagerung von 2-Lithium-3-isopropyl-furan an 3β-Tetrahydropyranyloxy-pregn-5-en-20-on". Zeitschrift für Chemie 14, № 7 (2010): 274–75. http://dx.doi.org/10.1002/zfch.19740140712.

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48

Robichaud, M., and G. Debonnel. "Modulation of the firing activity of female dorsal raphe nucleus serotonergic neurons by neuroactive steroids." Journal of Endocrinology 182, no. 1 (2004): 11–21. http://dx.doi.org/10.1677/joe.0.1820011.

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Important gender differences in mood disorders result in a greater susceptibility for women. Accumulating evidence suggests a reciprocal modulation between the 5-hydroxytryptamine (5-HT) system and neuroactive steroids. Previous data from our laboratory have shown that during pregnancy, the firing activity of 5-HT neurons increases in parallel with progesterone levels. This study was undertaken to evaluate the putative modulation of the 5-HT neuronal firing activity by different neurosteroids. Female rats received i.c.v. for 7 days a dose of 50 micro g/kg per day of one of the following steroids: progesterone, pregnenolone, 5beta-pregnane-3,20-dione (5beta-DHP), 5beta-pregnan-3alpha-ol,20-one, 5beta-pregnan-3beta-ol,20-one, 5alpha-pregnane-3,20-dione, 5alpha-pregnan-3alpha-ol,20-one (allopregnanolone, 3alpha,5alpha-THP), 5alpha-pregnane-3beta-ol,20-one and dehydroepiandrosterone (DHEA). 5beta-DHP and DHEA were also administered for 14 and 21 days (50 micro g/kg per day, i.c.v.) as well as concomitantly with the selective sigma 1 (sigma1) receptor antagonist NE-100. In vivo, extracellular unitary recording of 5-HT neurons performed in the dorsal raphe nucleus of these rats revealed that DHEA, 5beta-DHP and 3alpha,5alpha-THP significantly increased the firing activity of the 5-HT neurons. Interestingly, 5beta-DHP and DHEA showed different time-frames for their effects with 5beta-DHP having its greatest effect after 7 days to return to control values after 21 days, whereas DHEA demonstrated a sustained effect over the 21 day period. NE-100 prevented the effect of DHEA but not of 5beta-DHP, thus indicating that its sigma1 receptors mediate the effect of DHEA but not that of 5beta-DHP. In conclusion, our results offer a cellular basis for potential antidepressant effects of neurosteroids, which may prove important particularly for women with affective disorders.

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POLMAN, J., та A. KASAL. "ChemInform Abstract: Steroids. Part 360. The Synthesis of 5-Methyl-19-nor-5β-pregna-9, 16-diene-3,20-dione, 5-Methyl-19-nor-5β-pregna-9,10-diene-3,6,20- trione and Their Analogues with Anellated E Ring." ChemInform 23, № 13 (2010): no. http://dx.doi.org/10.1002/chin.199213280.

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Bruttomesso, Andrea, та Eduardo Gros. "First Synthesis of (20S) 3β,16β-Dihydroxy-5-pregnen-20,16-carbolactone (Diosgeninlactone)". Molecules 5, № 12 (2000): 564–65. http://dx.doi.org/10.3390/50300564.

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