172377-52-5

Upstream product

• 50-28-2 estradiol 
• 53-16-7 Estrone 
• 148672-09-7 estrone 3-O-sulfamate 
• 57-91-0 α-estradiol 
• 185910-40-1 17α-tert-butyldimethylsilyloxyestra-1,3,5(10)-trien-3-ol 
• 185910-39-8 (8R,9S,13S,14S,17R)-3,17-Bis-(tert-butyl-dimethyl-silanyloxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene 
• 185910-42-3 Sulfamic acid (8R,9S,13S,14S,17R)-17-(tert-butyl-dimethyl-silanyloxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl ester 

Relevant academic research and scientific papers

Inhibition of estrone sulfatase by aromatase inhibitor-based estrogen 3-sulfamates

Our rationale is based on the finding that estrone 3-sulfamate (EMATE, 2d), a typical estrone sulfatase (ES) inhibitor, can be hydrolyzed and the pharmacological effect of the free estrogen contributes to the bioactivity of the sulfamate. A number of 3-su

Synthesis of Tamoxifen-Artemisinin and Estrogen-Artemisinin Hybrids Highly Potent Against Breast and Prostate Cancer

In the search for new and effective treatments of breast and prostate cancer, a series of hybrid compounds based on tamoxifen, estrogens, and artemisinin were successfully synthesized and analyzed for their in vitro activities against human prostate (PC-3) and breast cancer (MCF-7) cell lines. Most of the hybrid compounds exhibit a strong anticancer activity against both cancer cell lines – for example, EC50 (PC-3) down to 1.07 μM, and EC50 (MCF-7) down to 2.08 μM – thus showing higher activities than their parent compounds 4-hydroxytamoxifen (afimoxifene, 7; EC50=75.1 (PC-3) and 19.3 μM (MCF-7)), dihydroartemisinin (2; EC50=263.6 (PC-3) and 49.3 μM (MCF-7)), and artesunic acid (3; EC50=195.1 (PC-3) and 32.0 μM (MCF-7)). The most potent compounds were the estrogen-artemisinin hybrids 27 and 28 (EC50=1.18 and 1.07 μM, respectively) against prostate cancer, and hybrid 23 (EC50=2.08 μM) against breast cancer. These findings demonstrate the high potential of hybridization of artemisinin and estrogens to further improve their anticancer activities and to produce synergistic effects between linked pharmacophores.

ENT-STEROIDS AS SELECTIVELY ACTIVE ESTROGENS

From EXEMP_CLAIMS : Ent-Steroids namely ent-Estriol ent-Estriol-3-sulfamate ent-Estriol-3-(N-acetyl)sulfamate ent-Estriol-3,16,17-tripropionate ent-Estrone-3-sulfamate ent-Estrone-3-(N-acetyl)sulfamate ent-Estradiol-3-sulfamate ent-Estradiot-3,17-disulfam

Industrially applicable process for the sulfamoylation of alcohols and phenols

This invention describes a safe method for the production of sulfamoyl chloride from chlorosulfonyl isocyanate and formic acid in the presence of a amide catalyst, taming the hazardous nature of this reaction by circumventing heat accumulation processes, as well as the sulfamoylation of alcohols and phenols with the resulting sulfamoyl chloride in N,N-dimethyl acetamide or N-methyl pyrrolidone thereby avoiding the formation of side-products which were inevitable with the methods of the prior art using dimethyl formamide or dichloromethane as a solvent. The current invention allows industrial scale applications and describes as an example the process of manufacture of the biologically active compound 17β-Hydroxyestra-1,3,5(10)-triene-3-yl sulfamate.

Steroid sulfamates, method for the production and use thereof

A novel class of gonane type and D-homo-gonane type steroids having sulfatase-inhibiting and/or estrogenic activity is presented for application in the pharmaceutical industry. The number and location of sulfamoyloxy groups on the steroids provides for sulfatase inhibiting and estrogenic activities that independently vary over a wide range, allowing the customization of the pharmaceutical for specific purposes, including treatment and diagnosis of estrogen-dependent tumors.

Pharmaceutical preparations containing estra-1,3,5(10)-triene derivatives

The invention concerns pharmaceutical preparations containing estra-1,3,5(10)-triene derivatives as active ingredients which carry a group of the general formula R—SO2—O—at their C3 position wherein R is a R1R2N group wherein R1 and R2 are independent of each other and represent a hydrogen atom, a C1-C5 alkyl radical or, together with the N atom, a polymethylene imino radical containing 4 to 6 C atoms, or a morpholino radical. The preparations according to the invention can be used for hormonal contraception and for hormon replacement therapy (HRT). They exhibit a low hepatic estrogenity.

Preparation and Characterization of the Sulphamates of Estra-3,17ξ-diols. Rapid Conversion of 16α-Fluoroestradiol into 16α-Fluoroestradiol-3,17β-disulphamate

Estradiols are able to form two monosulphamates and one disulphamate. In the present work all the sulphamates of 17α-estradiol, 17β-estradiol and 16α-fluoroestradiol were synthesized and characterized. For characterization NMR spectroscopy was used first of all. Because of its high sulphatase inhibitory efficiency 16α-fluoroestradiol-3,17-β-disulphamate found a special interest among the new sulphamates. Just the binding between sulphamate and sulphatase favoured 16α-[18F]fluorestradiol-3,17-β-disulphamate to a new radio-pharmaceutical which should be appropriate to image the active sites of sulphatase by positron emission tomography. The preparation of 16α-[18F]fluoroestradiol-3,17-β-disulphamate requires a simple and rapid procedure. The conditions for such a procedure were also elaborated using non-radioactive substances.

Synthesis of estrogen sulfamates: Compounds with a novel endocrinological profile

Estrogen sulfamates are promising hormones by oral administration. Therefore, generally applicable and convenient methods for the multigram synthesis of these derivatives are desirable. Numerous estra-1,3,5(10)- trienes derived from estrone, estradiol, 14α,15α-methylenestradiol, ethinylestradiol, and estriol have been esterified with sulfamoyl chloride and N-methylsulfamoyl chloride by a novel approach involving the use of 2,6- di-tert-butylpyridines as bases and chemoselective hydroxy group protections. These pathways circumvent the nonselective formation of esters and side reactions by in situ generated azasulfenes. For toxicological and clinical studies a new synthesis of estrone sulfamate on a 100-g scale was developed using dimethylformamide as the solvent and base.