158342-64-4Relevant academic research and scientific papers
Dehydroepiandrosterone derived imidazolium salts and their antimicrobial efficacy
Hryniewicka, Agnieszka,Niemirowicz-Laskowska, Katarzyna,Wielgat, Przemys?aw,Car, Halina,Hauschild, Tomasz,Morzycki, Jacek W.
, (2020/12/29)
Hybrid molecules consisting of steroid-imidazolium salts reveal interesting biological properties, especially regarding antimicrobial activities. Novel dehydroepiandrosterone derived imidazolium salts (11 salts) with side chains of different lengths were obtained in an efficient and straightforward synthetic route. Antimicrobial properties of new salts were examined by determining their minimum inhibitory concentrations (MICs). They were studied against several strains of bacteria, including clinical isolates of MRSA, and fungi. New compounds showed high activity against Gram-positive bacteria and Candida albicans as well as good compatibility with the representatives of the host cells when applied at concentrations corresponding to MIC value. The studies indicated high antimicrobial efficacy of imidazolium salts against the above-mentioned microorganisms with low hemolytic activity at a concentration that restricts the growth of the microorganisms. The interference of salts with the immune defense system, the influence on the biological activity of monocytes/macrophages measured by their viability and metabolic activity was also studied. The new compounds have shown immunoprotective properties.
Synthesis and anti-gastric cancer activity evaluation of novel triazole nucleobase analogues containing steroidal/coumarin/quinoline moieties
Zhao, Jian-Wei,Wu, Zeng-Hui,Guo, Jia-Wen,Huang, Ming-Jie,You, Ya-Zhen,Liu, Hong-Min,Huang, Li-Hua
supporting information, (2019/08/12)
A series of novel triazole nucleobase analogues containing steroidal/coumarin/quinoline moieties have been synthesized based on copper-catalyzed azide-alkyne cycloaddition (CuAAC). The anti-cancer activity of the new triazole nucleobase analogues was stud
Method for synthesizing 3 beta-hydroxyl-16-aryl androstane-5 (6), 8 (14), 15 (16)-triene-17-ketone
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Paragraph 0015, (2016/10/10)
The invention relates to a method for synthesizing 3 beta-hydroxyl-16-aryl androstane-5 (6), 8 (14), 15 (16)-triene-17-ketone. The method includes steps of (a), synthesizing (3 beta)-hyroxyl-16-bromine-androstane-5 (6)-alkene-17-ketone; (b), synthesizing (3 beta)-hydroxyl-androstane-5 (6), 8 (14), 15 (16)-triene-17-ketone which is an intermediate; (c), generating (3 beta)-hydroxyl-16-iondine-androstane-5 (6), 8 (14), 15 (16)-triene-17-ketone from a product obtained at the step (b) by means of iodination in solvent systems; (d), carrying out coupling reaction on a product obtained at the step (c) and arylboronic acid under the effects of palladium catalysts to obtain a target compound.
Synthesis and biological evaluation of 3β-androsta-5,8(14),15-trien-17-one derivatives as potential anticancer agents
Li, Yang,Liu, Jinliang,Wang, Lizhong,Qing, Xushun,Wang, Cunde
, p. 74 - 80 (2016/06/01)
A novel and operationally simple method for highly efficient synthesis of promising anti-cancer 3β-hydroxy-16-arylandrosta-5,8(14),15-trien-17-ones was reported. Compounds were tested for their cytotoxic activities against A549, SKOV3, MKN-45 and MDA-MB-4
Darzens reaction rate enhancement using aqueous media leading to a high level of kinetically controlled diastereoselective synthesis of steroidal epoxyketones
Li, Bo,Li, Chunbao
, p. 8271 - 8277 (2015/03/18)
Darzens reactions between halocarbonyls and aldehydes have been carried out in water in the presence of a Li+-containing base, a phase-transfer catalyst, and granular polytetrafluoroethylene under mechanical stirring. Reactions using both aromatic and aliphatic aldehydes produced epoxides stereoselectively in good to excellent yields. This is the first time that aliphatic aldehydes with α-H have been used in aqueous Darzens reactions. The Darzens reactions were much faster in water than in organic solvents. This aqueous rate enhancement occurred for Darzens reactions between enantiopure steroidal haloketones and aldehydes, yielding enantiopure spiroepoxides with a high level of kinetically controlled diastereoselectivity. Chromatography was avoided in the purifications of the steroidal spiroepoxides. This is an example of preparing enantiopure epoxyketones via aqueous Darzens reaction using chiral α-haloketone substrates.
Design and synthesis of novel D-ring fused steroidal heterocycles
Zhang, Bao-Le,Zhang, En,Pang, Lu-Ping,Song, Li-Xing,Li, Ya-Fei,Yu, Bin,Liu, Hong-Min
, p. 1200 - 1208 (2013/10/22)
Using dehydroepiandrosterone as the starting material, we have synthesized a series of steroid analogs possessing a D-ring fused with heterocycles which are pyridine, imidazo [2,1-b]thiazoles or substituted thiazole imines. All the final structures are first reported and identified by NMR and MS spectroscopys, the yields of these products are moderate to good and the reaction conditions are mild. The cytotoxicity of the synthesized compounds against EC-109(human esophageal carcinoma), EC-9706(human esophageal carcinoma), MGC-803(human gastric carcinoma) were investigated.
A facile total synthesis of drospirenone isomers containing 14β-hydrogen configuration
Wan, Wen,Ma, Guobin,Gao, Wei,Wang, Jing,Li, Lei,Rao, Shangqin,Zheng, Chunfang,Jiang, Haizhen,Deng, Hongmei,Hao, Jian
, p. 6597 - 6603 (2013/09/24)
A facile strategy for the preparation of two isomeric drospirenones 13 and 16 possessing a 14β-hydrogen was developed, using 3β-hydroxyandrost-5- en-17-one as the starting material. The total synthetic route involves eight steps, giving 2% overall yield. The structures of the main compounds 11, 13, 14 and 16 were determined by single crystal XRD analysis.
Novel steroid inhibitors of glucose 6-phosphate dehydrogenase
Hamilton, Niall M.,Dawson, Martin,Fairweather, Emma E.,Hamilton, Nicola S.,Hitchin, James R.,James, Dominic I.,Jones, Stuart D.,Jordan, Allan M.,Lyons, Amanda J.,Small, Helen F.,Thomson, Graeme J.,Waddell, Ian D.,Ogilvie, Donald J.
supporting information; experimental part, p. 4431 - 4445 (2012/09/11)
Novel derivatives of the steroid DHEA 1, a known uncompetitive inhibitor of G6PD, were designed, synthesized, and tested for their ability to inhibit this dehydrogenase enzyme. Several compounds with approximately 10-fold improved potency in an enzyme assay were identified, and this improved activity translated to efficacy in a cellular assay. The SAR for steroid inhibition of G6PD has been substantially developed; the 3β-alcohol can be replaced with 3β-H-bond donors such as sulfamide, sulfonamide, urea, and carbamate. Improved potency was achieved by replacing the androstane nucleus with a pregnane nucleus, provided a ketone at C-20 is present. For pregnan-20-ones incorporation of a 21-hydroxyl group is often beneficial. The novel compounds generally have good physicochemical properties and satisfactory in vitro DMPK parameters. These derivatives may be useful for examining the role of G6PD inhibition in cells and will assist the future design of more potent steroid inhibitors with potential therapeutic utility.
Design, synthesis and evaluation of novel 16-imidazolyl substituted steroidal derivatives possessing potent diversified pharmacological properties
Bansal, Ranju,Guleria, Sheetal,Thota, Sridhar,Bodhankar, Subhash L.,Patwardhan, Moreshwar R.,Zimmer, Christina,Hartmann, Rolf W.,Harvey, Alan L.
scheme or table, p. 621 - 629 (2012/05/20)
As a part of our investigations into the structural-activity relationship studies of a novel class of medicinally active 16-substituted steroids, several new 16-imidazolyl substituted steroidal derivatives have been synthesized and pharmacologically evaluated in the current study. The new steroidal analogues 5, 6, 8, 9, 11 and 12 exhibited moderate cytotoxic effects in sixty cancer cell lines derived from nine cancers types. The imidazolyl substituted steroidal derivatives 6 (DPJ-RG-1241) and 7 (RB-401) were obtained as the powerful inhibitors of aromatase with IC50 = 0.18 μM and IC50 = 0.168 μM, respectively, approximately 1.2 and 1.4 times more potent in comparison to standard drug exemestane. The bis-quaternary steroids 13 and 14 displayed potent skeletal muscle relaxant properties. An affinity constant of 0.007 μM was observed for compound 14 on frog rectus abdominis muscle preparation and 13 displayed a very high anticholinesterase activity K i = 25 nM, approximately 115-fold higher in comparison to standard drug galanthamine (Ki = 2.9 μM).
NOVEL SERIES OF IMIDAZOLYL SUBSTITUTED STEROIDAL AND INDAN-1-ONE DERIVATIVES
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Page/Page column 18, (2012/12/13)
The present invention provides a novel series of imidazolyl substituted steroidal and indan-1-one derivatives and salts thereof having the following general structural formulae (A and B)
