53906-49-3

Usage

Uses

Used in Pharmaceutical Research:
(3β,20S)-20-Formyl-3-hydroxy-5-pregnene is used as a research compound for the development of novel anti-parasitic agents. Its potential as an anti-trypanosomal and anti-leishmanial agent makes it a valuable candidate for combating tropical diseases such as Chagas disease and leishmaniasis, which are caused by Trypanosoma and Leishmania parasites, respectively.
Used in Anthelmintic Applications:
In addition to its anti-parasitic properties, (3β,20S)-20-Formyl-3-hydroxy-5-pregnene may also be utilized as an anthelmintic agent, targeting various helminth parasites that cause infections in humans and animals. Its effectiveness against these parasites could lead to the development of new treatments for helminthic infections.
Used in Steroid Synthesis:
Due to its structural features, (3β,20S)-20-Formyl-3-hydroxy-5-pregnene can be employed as a key intermediate in the synthesis of various steroidal compounds with diverse biological activities. Its use in this capacity can contribute to the development of new drugs with applications in different therapeutic areas, such as hormonal regulation, inflammation, and immune response modulation.

Upstream product

• 32212-73-0 5α,6β-dibromostigmastan-3β-yl acetate 
• 83-48-7 24ξ-24-ethylcholest-5,22-dien-3β-ol 
• 83-48-7 stigmasterol 
• 4651-48-3 stigmasterol acetate 
• 145-13-1 Pregnenolone 
• 287471-28-7 stigmast-4,22-dien-3β-(2-tetrahydropyranyl)ether 
• 83-48-7 Stigmasterol 
• 1474-14-2 3β-acetoxybisnor-5-cholenic acid 
• 55509-37-0 3β-acetoxy-23,24-bisnor-chol-5-en-22-ol 
• 497841-91-5 5α,6β-dibromostigmast-22-en-3β-(2-tetrahydropyranyl)ether 
• 86400-70-6 (3S,8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-17-[(E)-1-methyl-2-(2-trimethylsilanyl-ethoxy)-vinyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 86400-71-7 (3S,8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-17-[(Z)-1-methyl-2-(2-trimethylsilanyl-ethoxy)-vinyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 10211-88-8 (20S)-3β-acetoxybisnorchol-5-en-22-al 

Downstream Products

• 26033-10-3 E/Z-cholesta-5,22-dien-3β-ol 
• 35882-85-0 26,27-dinorergost-5-ene-3β,24-diol 
• 333973-17-4 (2R,4S,5S)-5-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-ethyl-4-(imidazole-1-carbothioyloxy)-hexanoic acid ethyl ester 
• 333972-96-6 (4S,5S)-4-Benzyloxy-5-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylene-hexanoic acid ethyl ester 
• 333972-97-7 (4R,5S)-4-Benzyloxy-5-[(3S,8S,9S,10R,13S,14S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylene-hexanoic acid ethyl ester 

Relevant academic research and scientific papers

Sterol compound and its pharmaceutically acceptable salt or prodrug, and application thereof

The present invention discloses a sterol compound and its pharmaceutically acceptable salt or prodrug, and an application thereof in the prevention or treatment of malignant tumors associated with LXR. The compound has an inhibitory ability against various malignant tumors in in-vitro experiments, and also has an inhibitory ability against malignant tumors malignant tumors in in-vivo experiments.The sterol skeleton compound has the equivalent curative effect on the malignant tumors with cytotoxic drugs currently used for treating the tumors, and has the same therapeutic effect with positive drugs for evaluating the drug effect of the compound. The compound has the advantages of good antitumor activity, good safety, no side effects caused by the positive drugs, and facilitation of enhancement of the immune function of animals. The sterol compound has a potential to become a safe and effective broad-spectrum antitumor drug.

Preparation method for 3beta-hydroxy-ergosta-5-ene steroid compound

The invention provides a novel synthetic method for 3beta-hydroxy-ergosta-5-ene steroid derivative. The method includes the following steps: 1, taking stigmasterol 1-a as an initial raw material, andpreparing an intermediate aldehyde compound 1-b through multi-step reaction; 2, starting from the compound 1-b to obtain a compound 1-c through witting reaction; 3, preparing a compound 1-d from the compound 1-c through a reduction reaction; 4, obtaining a compound 1 by the compound 1-d through a nucleophilic addition reaction; and 5, preparing a 3beta-hydroxy-ergosta-5-ene steroid from the compound 1. Compared with the prior art, the method realizes the massive and efficient preparation of the compound from stigmasterol; and synthetic raw materials are easy to obtain, synthetic processes aresimple in operation, and the method is high in yield.

3beta-hydroxy-ergosta-5-ene steroid derivative and drug application thereof

The invention provides a structure of a 3beta-hydroxy-ergosta-5-ene steroid compound, and applications of the compound and the pharmaceutically acceptable form of chemical protection or a prodrug in the preparation of drugs capable of preventing or treating LXRbeta related metabolic syndromes. The LXRbeta related metabolic syndromes include hyperlipidemia, atherosclerosis or hypertension. Throughthe discovery of the evaluation of lipid-lowering activity in animal bodies, the compound has obvious effects on lipid lowering, so that the compound has potentials of further developing into a novellipid-lowering drug.

Novel method used for synthesizing cholesterol

The invention discloses a novel method used for synthesizing cholesterol. The novel method comprises following steps: 1, stigmasterol 02 is dissolved in an organic solvent I, and is subjected to silicon etherification reaction with trimethylchlorosilane under the effect of a catalyst, and a compound 03 is obtained via water washing and condensation; 2, the compound 03 is dissolved in an organic solvent II for ozone oxidation, zinc powder and acetate acid gracial are added for reduction, after reduction, filtering, washing, and condensation are carried out so as to obtain a compound 04; 3, triphenylphosphine is reacted with 1-halogenated-3-methyl butane so as to obtain 3-methyl butyl triphenyl halogenated phosphorus, the 3-methyl butyl triphenyl halogenated phosphorus is added into an aprotic solvent, a strong base is added, wittig reaction with a compound 4 is carried out, and neutralizing, condensation, and filtering are carried out so as to obtain a compound 05; 4, the compound 05 is subjected to selective hydrogenation in a solvent III under the action of a catalyst and a passivator, and filtering, condensation, and crystallization are carried out so as to obtain cholesterol 01. The novel method is simple; raw materials are cheap; the novel method is economic and is friendly to the environment, and is convenient for industrialized production.

Synthesis of some steroidal derivatives with side chain of 20-and 22-hydrazone aromatic heterocycles and their antiproliferative activity

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.

22-abeo-stigmasterol benzimidazole compound as well as preparation method and application thereof

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.

22-nor-stigmasta thiosemicarbazone compound and preparing method and application thereof

The invention discloses a 22-nor-stigmasta thiosemicarbazone compound and a preparing method and application thereof. The structural formula of the 22-nor-stigmasta thiosemicarbazone compound is shown in the description. In vitro cancer cell growth and proliferation activity inhibition tests show that the prepared 22-nor-stigmasta thiosemicarbazone compound has a remarkable inhibition effect on various tumor cell strains such as human nipple thyroid gland cancer cells, human oral cavity epidermoid carcinoma cells and cervical cancer. Meanwhile, the 22-nor-stigmasta thiosemicarbazone compound is free of cytotoxicity on human kidney epithelial cells (HEK293T) and can be used for preparing medicine for treating cancer.

SAR studies on azasterols as potential anti-trypanosomal and anti-leishmanial agents

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.

Evaluation of azasterols as anti-parasitics

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 (III): synthesis and structural elucidation of 24-methylenecholest-4-en-3beta,6 alpha-diol.

Using stigmasterol as the starting material, 24-methylenecholest-4-en-3beta,6 alpha-diol (2) was synthesized in eight steps in 13% overall yield. The introduction of the sterol side-chain was carried out using (3-methyl-2-oxobutyl)-triphenylarsonium bromide (11) and K(2)CO(3) in a solid-liquid phase-transfer Wittig reaction. Construction of the steroidal nucleus was finished by oxidation of 24-methylenecholest-5-en-3beta-ol (9) with pyridinium chlorochromate (PCC) in dichloromethane at ambient temperature and by reduction of 24-methylenecholest-4-en-3,6-dione (10) with NaBH(4) in the presence of CeCl(3).7H(2)O.