10211-88-8Relevant academic research and scientific papers
SAR studies on azasterols as potential anti-trypanosomal and anti-leishmanial agents
Gigante, Federica,Kaiser, Marcel,Brun, Reto,Gilbert, Ian H.
, p. 5950 - 5961 (2009)
There is an urgent need for the development of new drugs for the treatment of neglected tropical diseases such as human African trypanosomiasis, Chagas disease and leishmaniasis. Azasterols, have been shown to have activity against the parasites which cause these diseases. In this paper we report synthesis of new azasterols and subsequent analysis of the SAR. The chemistry focused on variations in the ester at the 3β-position of the sterol and the position of the nitrogen in the side chain. The data allowed us to derive preliminary pharmacophore models for the activity of the azasterols against the parasites which cause these diseases.
A simple synthesis of 3β-Acetoxy-20-oxomethylpregn-5-ene and 3β-Acetoxy-20-hydroxymethylpregn-5-ene
Drozdov,Timofeev,Misharin
, p. 96 - 98 (2006)
3β-Acetoxy-20-oxomethylpregn-5-ene and 3β-acetoxy-20- hydroxymethylpregn-5-ene were synthesized from (22R,23R)-sitost-5-ene-3β, 22,23-triol in 66% overall yields. Pleiades Publishing, Inc., 2006.
Novel industrial method for preparing vitamin D3 by taking stigmasterol as raw material
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Paragraph 0010; 0037-0040, (2021/05/05)
The invention provides a novel industrial method for preparing vitamin D3 by taking stigmasterol as a raw material. The method comprises the following steps: sequentially carrying out hydroxyl acetylation, side chain oxidation, side chain isopentane reduction and hydrogenation on stigmasterol to obtain cholesterol acetate, and then sequentially carrying out oxidation, hydrazone formation, hydrazone removal, hydrolysis, illumination and the like to obtain the vitamin D3. The invention provides a novel method for preparing vitamin D3 from stigmasterol, and the method has the advantages of mild reaction conditions and high yield, and is suitable for industrial production.
Synthesis of some steroidal derivatives with side chain of 20-and 22-hydrazone aromatic heterocycles and their antiproliferative activity
Gan, Chunfang,Liu, Liang,Cui, Jianguo,Liu, Zhiping,Shi, Haixin,Lin, Qifu,Sheng, Haibing,Yang, Chunhui,Huang, Yanmin
, p. 375 - 383 (2017/06/20)
Background: The modification of steroidal structure is commonly used to change the biological activity of steroids in medicinal chemistry. Some steroids containing heterocycles exhibit distinct cytotoxicity against various cancer cell lines and have been receiving wide attention over the years by medicinal chemists for drug discovery. Methods: Using pregnenolone and stigmasterol as starting materials, via different chemical reaction, two series of heterosteroids with side chain of 20- and 22-hydrazone aromatic cycles or heterocycles in their structures were synthesized and characterized by IR, NMR and HRMS. The antiproliferative activity of the compounds in vitro was evaluated against human HT-29, HeLa, Bel 7404 and SGC 7901 cancer cells by MTT assays. Results: The steroidal compounds with side chain of 20-hydrazone aromatic cycles or heterocycles exhibited distinct cytotoxicity. However, analogues with the side chain of 22-hydrazone resulted in a dramatic decrease of the cytotoxicity. The result of Annexin V assay showed that the 20-hydrazone compounds were potent apoptotic inducers against these carcinoma cells. Conclusion: Steroidal compounds with the side-chain of 20-hydrazone aromatic heterocycles exhibit distinct antiproliferative activity in vitro. However, the compounds with the side-chain of 22-hydrazone aromatic heterocycle decreased the cytotoxicity of the compounds.
NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
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Paragraph 0574; 0579; 0580, (2016/02/16)
Provided are methods of evaluating or treating a patient, e.g., a patient having a disorder described herein, comprising: a) optionally, acquiring a patient sample; b) acquiring an evaluation of and/or evaluating the sample for an alteration in the level S24(S)-hydroxycholesterol compared to a reference standard.
22-abeo-stigmasterol benzimidazole compound as well as preparation method and application thereof
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Paragraph 0046; 0050, (2016/10/09)
The invention discloses a 22-abeo-stigmasterol benzimidazole compound as well as a preparation method and application thereof. The structural formula of the 22-abeo-stigmasterol benzimidazole compound is shown in the specification; experiments for in-vitro inhibition of growth and proliferation activities of cancer cells show that the 22-abeo-stigmasterol benzimidazole compound prepared by the preparation method has remarkable inhibition effect to multiple tumor cell strains such as human papillary thyroid cancer cells, human oral epidermoid carcinoma cells, cancer cell strains of cervical cancer and the like. Meanwhile, the 22-abeo-stigmasterol benzimidazole compound has no cytotoxicity to human kidney epithelial cells (HEK293T) and can be applied to the preparation of drugs for treating cancers.
NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
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Paragraph 00379, (2013/03/26)
Compounds are provided according to Formula (I) and pharmaceutically acceptable salts thereof, wherein Z is a group of the formula (i), (ii), (iii), (iv), or (v), and wherein L1, L2, L3, X1, X2, Y, Rz4, Rz5, Rz6, n, R1, R2, R3a, R3b, R4a, R4b, R6a, R6b, R7a, R7b, R11a, R11b, R14, R17, R19, R20, R23a, R23b, and R24 are as defined herein, and pharmaceutical compositions thereof. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of CNS-related conditions in mammals.
Evaluation of azasterols as anti-parasitics
Gros, Ludovic,Lorente, Silvia Orenes,Jimenez, Carmen,Yardley, Vanessa,Rattray, Lauren,Wharton, Hayley,Little, Susan,Croft, Simon L.,Ruiz-Perez, Luis M.,Gonzalez-Pacanowska, Dolores,Gilbert, Ian H.
, p. 6094 - 6103 (2007/10/03)
In this article, the design and synthesis of some novel azasterols is described, followed by their evaluation against Trypanosoma brucei rhodesiense, T. cruzi, Leishmania donovani, and Plasmodium falciparum, the causative agents of human African trypanosomiasis, Chagas disease, leishmaniasis, and malaria, respectively. Some of the compounds showed anti-parasitic activity. In particular, a number of compounds appeared to very potently inhibit the growth of the blood stream form T. b. rhodesiense, with one compound giving an IC 50 value of 12 nM. Clear structure activity relationships could be discerned. These compounds represent important leads for further optimization. Azasterols have previously been shown to inhibit sterol biosynthesis in T. cruzi and L. donovani by the inhibition of the enzyme sterol 24-methyltransferase. However, in this case, none of the compounds showed inhibition of the enzyme. Therefore, these compounds have an unknown mode of action.
Synthesis of polyhydroxysterols (I): Synthesis of 24-methylenecholest-4-en-3β,6β-diol, a cytotoxic natural hydroxylated sterol
Cui, JianGuo,Zeng, LongMei,Su, JingYu,Lu, WeiGang
, p. 33 - 38 (2007/10/03)
Starting from stigmasterol (2), 24-methylenecholest-4-en-3β,6β-diol (1), a cytotoxic natural dihydroxylated sterol, was synthesized via 10 steps in 20% overall yield. The introduction of a side-chain of sterol was achieved by solid-liquid phase-transfer Wittig reaction using (3-methyl-2-oxo)butyltriphenylarsonium bromide (12) and K2CO3. Construction of the steroidal nucleus was finished by the addition of 3β-acetoxycholest-5,6-en-24-one (7) with NBA in dioxane under ambient temperature and by the elimination of 3β, 6β-diacetoxy-5a-bromocholestane-24-one (9). The spectral data of the synthetic product (1) are completely consistent with those of the natural compound (1). Copyright (C) 2001 Elsevier Science Inc.
Fluorescent-labeled analogues of cholesterol
Grechishnikova,Molotkovsky
, p. 394 - 399 (2007/10/03)
Starting from pregnenolone acetate, new fluorescent analogues of cholesterol, (22E, 20R)-3β-hydroxy-23-(9-anthryl)-24-norchola-5,22-diene and its 205-isomer, were synthesized. They bear an anthrylvinyl group instead of the C22-C27 fragment of the sterol alkyl chain and possess fluorescent properties characteristic of anthrylvinyl probes. Both analogues can be easily incorporated into the phospholipid bilayer and used for the study of membrane systems.
