10481-80-8Relevant articles and documents
Synthesis and bioevaluation of novel steroidal isatin conjugates derived from epiandrosterone/androsterone
Ke, Shaoyong,Zhang, Zhigang,Liu, Manli,Fang, Wei,Huang, Daye,Wan, Zhongyi,Zhou, Ronghua,Wang, Kaimei,Shi, Liqiao
, p. 1607 - 1614 (2019)
Steroids are classes of natural products widely distributed in nature, which have been demonstrated to exhibit broad biological functions, and have also attracted increasing interest from bioorganic and pharmaceutical researches. In order to develop novel chemical entities as potential cytotoxic agents, a series of steroidal isatin conjugations derived from epiandrosterone and androsterone were efficiently prepared and characterized, and all these obtained compounds were screened for their potential cytotoxic activities. The preliminary bioassay indicated that most of the newly synthesized compounds exhibited good cytotoxic activities against human gastric cancer (SGC-7901), melanoma (A875), and hepatocellular liver carcinoma (HepG2) cell lines compared with 5-fluorouracil (5-FU), which might be considered as promising scaffold for further development of potential anticancer agents.
Synthesis, Characterization, and Biological Properties of Steroidal Ruthenium(II) and Iridium(III) Complexes Based on the Androst-16-en-3-ol Framework
Koch, Vanessa,Meschkov, Anna,Feuerstein, Wolfram,Pfeifer, Juliana,Fuhr, Olaf,Nieger, Martin,Schepers, Ute,Br?se, Stefan
, p. 15917 - 15926 (2019)
A range of novel cyclometalated ruthenium(II) and iridium(III) complexes with a steroidal backbone based on androsterone were synthesized and characterized by NMR spectroscopy and X-ray crystallography. Their cytotoxic properties in RT112 and RT112 cP (cisplatin-resistant) cell lines as well as in MCF7 and somatic fibroblasts were compared with those of the corresponding nonsteroidal complexes and the noncyclometalated pyridyl complexes as well as with cisplatin as reference. All steroidal complexes were more active in RT112 cP cells than cisplatin, whereby the cyclometalated pyridinylphenyl complexes based on 5c showed high cytotoxicity while maintaining low resistant factors of 0.33 and 0.50.
Steroid derivative containing isatin unit as well as preparation method and application thereof
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Paragraph 0029; 0032-0034; 0037; 0040-0042, (2019/06/07)
The invention provides a steroid derivative containing an isatin unit as well as a preparation method and application thereof. The structure formula of the steroid derivative containing the isatin unit is as shown in the formula I (the formula is shown in the description). The preparation method of the compound comprises the steps that (1) a compound epiandrosterone or androsterone serves as an initial raw material to make dehydration reaction with hydrazine hydrate to obtain an intermediate; (2) the intermediate makes condensation reaction with substituation isatin in a solvent, so that a first kind of target compound with R1 being H is obtained; and (3) the first kind of target compound with R1 being H makes esterification reaction with chloride with the structure formula being R1Cl in asolvent, so that a second kind of target compound with R1 being CH3CO, CH3CH2CO, CH3SO2 or PhCO is obtained. The compound can serve as a substite product used for preparing active components of novelanticancer drugs.
Crystal structures and Hirshfeld surface analyses of the di- and tri-hydrates of (5α,17E)-17-hydrazonoandrostan-3-ol: Significant differences in the hydrogen bonding patterns and supramolecular arrangements
Gomes, Ligia R.,Low, John N.,Turner, Alan B.,Baddeley, Thomas C.,Wardell, James L.
, p. 92 - 103 (2018/10/20)
The crystal structures, Hirshfeld surface analyses and electrostatic potential surfaces of the di- and tri-hydrates of (5α,17E)-17-hydrazonoandrostan-3-ol, 3, namely [3·(H2O)2] and [3·(H2O)3], are reported. The trihydrate, isolated from a solution of 3 in moist methanol, recrystallizes in the orthorhombic space group, P212121, while that of the dihydrate, isolated from a 1:1 aqueous methanol solution, recrystallizes in the monoclinic space group, P21. The asymmetric unit of the trihydrate involves one steroid and three water molecules, while that of the dihydrate has two similar but independent steroid molecules and four hydrate molecules. Very similar conformations are found for the steroid molecules in both hydrates. As expected, the different mole ratios of water: steroid have major influences on the structures. In both cases, complex crystal structures are constructed from various classical hydrogen bonds, involving the hydrate molecules and the hydroxy and hydrazonyl moieties of the steroid. In the trihydrate, there are no direct connections between the steroid molecules, instead the water molecules link the steroid molecules, with only weak van der Waals forces between the steroid molecules. There are some direct links between the steroid molecules in the dihydrate, involving O–H(steroid hydroxyl)?O(steroid oxo) hydrogen bonds, in a head to head fashion, and O–H?N(hydrazonyl) hydrogen bonds, in a head to tail fashion. However, the major occurrence throughout the structure is of steroid molecules linked by water molecules.
Stille and Suzuki Cross-Coupling Reactions as Versatile Tools for Modifications at C-17 of Steroidal Skeletons – A Comprehensive Study
Koch, Vanessa,Nieger, Martin,Br?se, Stefan
supporting information, p. 832 - 840 (2017/03/11)
Herein, we report on a comparative Stille and Suzuki cross-coupling study of steroidal vinyl (pseudo)halides with different boronic acids and tributyltin organyls. Furthermore, we have investigated the “inverse” case of those cross-coupling reactions, i.e., the reaction of a steroidal vinylpinacolatoborane or a tributyltin steroid with various bromides. The development of both methods allows the introduction of different residues at C-17 of steroid skeletons providing access to a broad variety of steroid analogues which are of high interest for biological screenings or natural product synthesis. (Figure presented.).
Abiraterone acetate reducing impurity and preparation method thereof
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Paragraph 0018, (2017/10/22)
The invention discloses an abiraterone acetate reducing impurity and a preparation method thereof. The impurity is 17-(3-pyridyl) androstane-3 beta-acetoxyl. The preparation method of the impurity includes the steps: taking dehydroepiandrosterone as a starting material; performing catalytic hydrogenation by palladium carbon to obtain (3 beta)-3-hydroxy-17-sterone; performing reaction by hydrazine hydrate to obtain 17-hydrazono-androstane-3 beta-alcohol; performing iodine substitution to obtain 17-iodine-androstane-3 beta-alcohol; reacting the 17-iodine-androstane-3 beta-alcohol with borane reagents under palladium catalysis to obtain 17-(3-pyridyl) androstane-3 beta-alcohol; performing acetic anhydride acetylation to obtain the abiraterone acetate reducing impurity 17-(3-pyridyl) androstane-3 beta-acetoxyl.
Synthesis and biological evaluation of some nitrogen containing steroidal heterocycles
Abdelhalim, Mervat M.,Kamel, Eman M.,Rabie, Samira T.,Mohamed, Nadia R.
scheme or table, p. 78 - 84 (2011/03/18)
epi-Androsterone 1 was converted into its hydrazone derivative through the reaction with hydrazine hydrate 80%. Hydrazonoandrostane derivative 2b reacted with hydrazonoyl halides in the presence of K2CO3 forming the corresponding hyd
Facile synthesis and in vitro cytotoxic evaluation of novel thiadiazole, pyrazole, and dithiole-androstane derivatives
Mohamed, Nadia R.,Elmegeed, Gamal A.,Abdelhalim, Mervat M.,Rady, Hanaa M.
body text, p. 848 - 856 (2010/08/19)
In the aim of identifying new steroidal cytotoxic agents with potential antiproliferative activity against hepatoma cell lines (Hep-G2), we synthesized modified steroids containing the thiadiazole, pyrazole, or dithiole moiety. Epiandrosterone 1 reacted with carbon disulfide and sodium hydride to furnish -oxoketene dithio-disodium salt 2. Treatment of 2 with the hydrazonoyl halides 5a-d produced the thiadiazole anellated androstanone 7a-d, respectively. The reaction of 1 with hydrazine hydrate produced the hydrazide adduct 8, which cyclized upon reflux in acetic acid to form the condensed pyrazoloandrostanone derivative 9. Interaction of 8 with carbon disulfide and sodium hydride formed the disodium salt 10, which reacted with ethylchloroacetate to furnish the final adduct, dithioloandrostane derivative, 13. Compounds 7a, 7d, 9, and 13 were examined for their cytotoxicity against a panel of hepatoma cell lines (Hep-G2) using MTT assay. The results provide that, at incubation time 72 h, in DMSO, compound 7d (50 mol/mL) showed the most significant cytotoxic effect at P 0.05. The higher dose (100 mol/mL) of compound 7d, at 48 h incubation, reversed the effect causing resistance and the growth rate return to the control level. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
Microbiological hydroxylation of some epoxy steroids by the fungus Mucor plumbeus
Alfooty, Khalid. O.
body text, p. 314 - 317 (2009/05/30)
The preparation of epoxy steroids derived from testosterone, dehydroisoandrosterone and epiandrosterone using m-chloroperbenzoic acid and their biotransformation by the fungus Mucor plumbeus is described. The results reveal an effect of the epoxide on the biotransformation.
