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6?-Acetamido-5?-hydroxy-cholestan-3?-yl acetate.

ABSTRACT: The title steroid, C(31)H(53)NO(4), was prepared from the corresponding 5?,6?-epoxy-cholestane. The conformation of the six-membered rings is close to a chair form, while the five-membered ring adopts a twist conformation. The hydroxyl and acetamide groups are in axial positions. The nucleophilic species bound to the steroid nucleus at position 6 by the ?-face, whereas the hydroxyl group at position 5 has ?-orientation. All rings are trans-fused. The crystal packing shows that the mol-ecules related by twofold symmetry exist as O-H?O hydrogen-bonded dimers.

SUBMITTER: Pinto RM

PROVIDER: S-EPMC2959794 | biostudies-literature |

REPOSITORIES: biostudies-literature

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6β-Chloro-5α-hydr-oxy-20-oxopregnan-3β-yl acetate.

Project description:The title steroid, C(23)H(35)ClO(4), is a pregnane derivative prepared by ring opening of the corresponding 5α,6α-ep-oxy steroid with BiCl(3). There are two symmetry-independent mol-ecules in the asymmetric unit that show no significant differences concerning bond lengths and angles. The conformation of the six-membered rings in both mol-ecules is close to a chair form, while the five-membered ring adopts an envelope conformation. All rings in both mol-ecules are trans-fused. The mol-ecules are held together by an extensive O-H⋯O hydrogen-bonding network.

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Androstane-3β,5α,6β,17β-tetrol tri-hydrate.

Project description:The title hydrated tetrol, C(19)H(32)O(4)·3H(2)O, was synthesized by stereoselective reduction of the compound 3β,5α,6β-trihy-droxy-androstan-17-one. All rings are fused trans. The organic mol-ecules are connected head-to-tail along the c axis via O-H⋯O hydrogen bonds. Layers of water mol-ecules in the ab plane inter-connect these chains. A quantum chemical ab initio Roothan Hartree-Fock calculation of the isolated mol-ecule gives values for the mol-ecular geometry close to experimentally determined ones, apart from the C-O bond lengths, whose calculated values are significantly smaller than the measured ones, probably a consequence of the involvement of the C-OH groups in the hydrogen-bonding network.

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16α-Bromo-17β-hydr-oxy-5α-androstan-3β-yl acetate.

Project description:The title compound, C(21)H(33)BrO(3), an inter-mediate in the synthesis of the neuromuscular blocking agent rocuronium bromide, contains two independent mol-ecules in the asymmetric unit, which have almost identical geometries: in both mol-ecules, the steroidal rings A, B and C have slightly flattened chair conformations and ring D assumes a half-chair conformation. In the crystal, O-H⋯O hydrogen bonds and weak C-H⋯O and C-H⋯Br inter-actions help to establish the packing.

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3β, 6β-dichloro-5-hydroxy-5α-cholestane facilitates neuronal development through modulating TrkA signaling regulated proteins in primary hippocampal neuron.

Project description:Potentiating neuritogenesis through pharmacological intervention might hold therapeutic promise in neurodegenerative disorders and acute brain injury. Here, we investigated the novel neuritogenic potentials of a steroidal chlorohydrin, 3β, 6β-dichloro-5-hydroxy-5α-cholestane (hereafter, SCH) and the change in cellular proteome to gain insight into the underlying mechanism of its neurotrophic activity in hippocampal neurons. Morphometric analysis showed that SCH promoted early neuronal differentiation, dendritic arborization and axonal maturation. Proteomic and bioinformatic analysis revealed that SCH induced upregulation of several proteins, including those associated with neuronal differentiation and development. Immunocytochemical data further indicates that SCH-treated neurons showed upregulation of Hnrnpa2b1 and Map1b, validating their proteomic profiles. In addition, a protein-protein interaction network analysis identified TrkA as a potential target connecting most of the upregulated proteins. The neurite outgrowth effect of SCH was suppressed by TrkA inhibitor, GW441756, verifying TrkA-dependent activity of SCH, which further supports the connection of TrkA with the upregulated proteins. Also, the computational analysis revealed that SCH interacts with the NGF-binding domain of TrkA through Phe327 and Asn355. Collectively, our findings provide evidence that SCH promotes neuronal development via upregulating TrkA-signaling proteins and suggest that SCH could be a promising therapeutic agent in the prevention and treatment of neurodegenerative disorders.

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Effect of a synthetic steroid 5α-androst-3β, 5α, 6β-triol on gene expression in irradiated BV2 cells

Project description:We aimed to study the potential role and underlying mechanism of 5α-androst-3β, 5α, 6β-triol on irradiated BV2 cells. We established radiation induced BV2 cells injury model and pretreated with 5α-androst-3β, 5α, 6β-triol or vehicle. We then performed gene expression profiling analysis using data obtained from RNA-seq of different groups.

2024-04-18 | GSE230636 | GEO

5α-Androst-3-en-17β-yl acetate.

Project description:In the crystal structure of the title compound, C(21)H(32)O(2), ring A is highly distorted, with a conformation inter-mediate between 10β-sofa and 1α,10β-half chair; rings B and C have slightly flattened chair conformations. Ring D assumes an unusual 13β-envelope conformation, probably induced by the acet-oxy substituent. Cohesion of the crystal structure is due only to weak van der Waals inter-actions.

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3β,6β-Diacet-oxy-5,9α-dihy-droxy-5α-cholest-7-en-11-one acetic acid 0.04-solvate.

Project description:The title compound, C31H48O7·0.04CH3COOH, is a polyoxy-genated steroid obtained by selective chemical oxidation of 7-de-hydro-cholesteryl acetate. The asymmetric unit comprises three mol-ecules of the steroid (Z' = 3) and a mol-ecule of acetic acid which has occupancy factor 0.131 (5). The geometric parameters of the independent mol-ecules do not reveal significant differences. In one mol-ecule, the terminal isopropyl group is disordered over two sets of sites with occupancy ratio 0.869 (5):0.131 (5). The three mol-ecules reveal different hydrogen-bonding patterns. Each of them is involved in an intra-molecular S(6) hydrogen-bonding motif, involving hy-droxy groups as donor and acceptor. In the crystal, two independent mol-ecules form dimers through hydrogen bonding between an OH donor and an acetate carbonyl acceptor, giving rise to R 2 (2)(16) ring patterns. A single hydrogen bond between the OH group and a ketone carbonyl group is observed between two symmetry-independent mol-ecules.

| S-EPMC3685037 | biostudies-literature

6β-Methyl-3,20-dioxopregn-4-en-17-yl acetate.

Project description:The title compound, C(24)H(34)O(4), is a precursor of Megestrol acetate. Ring A has a half-chair conformation [Q = 0.446 (3) Å, θ = 54.6 (4)° and ϕ = 9.5 (4)°]. Ring D adopts a 13β-envelope conformation [Q = 0.463 (2) Å and ϕ = 188.2 (3)°].

| S-EPMC3343965 | biostudies-literature

Cholestane-3β,5α,6β-triol: high levels in Niemann-Pick type C, cerebrotendinous xanthomatosis, and lysosomal acid lipase deficiency.

Project description:Niemann-Pick type C (NPC) is a progressive neurodegenerative disease characterized by lysosomal/endosomal accumulation of unesterified cholesterol and glycolipids. Recent studies have shown that plasma cholestane-3β,5α,6β-triol (CT) and 7-ketocholesterol (7-KC) could be potential biomarkers for the diagnosis of NPC patients. We aimed to know the sensitivity and specificity of these biomarkers for the diagnosis of NPC compared with other diseases that can potentially lead to oxysterol alterations. We studied 107 controls and 122 patients including 16 with NPC, 3 with lysosomal acid lipase (LAL) deficiency, 8 with other lysosomal diseases, 5 with galactosemia, 11 with cerebrotendinous xanthomatosis (CTX), 3 with Smith-Lemli-Opitz, 14 with peroxisomal biogenesis disorders, 19 with unspecific hepatic diseases, 13 with familial hypercholesterolemia, and 30 with neurological involvement and no evidence of an inherited metabolic disease. CT and 7-KC were analyzed by HPLC-ESI-MS/MS as mono-dimethylglycine derivatives. Levels of 7-KC were high in most of the studied diseases, whereas those of CT were only high in NPC, LAL, and CTX patients. Consequently, although CT is a sensitive biomarker of NPC disease, including those cases with doubtful filipin staining, it is not specific. 7-KC is a very unspecific biomarker.

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3α,4α-Ep-oxy-5α-androstan-17β-yl acetate.

Project description:The title compound, C(21)H(32)O(3), results from modifications of the A and D rings of the aromatase substrate androstenedione. Ring A adopts a conformation between 10β-sofa and 1α,10β half-chair. Rings B and C are in slightly flattened chair conformations. Ring D approaches a 13β-envelope conformation, probably due to the acet-oxy substituent, and shows a very short Csp(3)-Csp(3) bond next to the epoxide ring, which is characteristic of 3-4 epoxides. .

| S-EPMC2968911 | biostudies-literature

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