148672-09-7

Basic information

• Product Name: ESTRONE 3-O-SULFAMATE
• Synonyms: ESTRONE 3-O-SULFAMATE;ESTRONE 3-SULFAMATE;ESTRONE SULFAMATE;ESTRONE O-SULFAMATE;1,3,5[10]-ESTRATRIEN-3-OL-17-ONE SULFAMATE;3-HYDROXY-1,3,5[10]-ESTRATRIEN-17-ONE 3-SULFAMATE;Estrone 3-sulfamate, Estrone O-Sulfamate, Estrone Sulfamate;1,3,5(10)-Estratrien-17-one 3-sulfamate
• CAS NO: 148672-09-7
• Molecular Formula: C₁₈H₂₃NO₄S
• Molecular Weight: 349.44452
• Product Categories: Steroids & Hormones - 13C & 2H;Inhibitors;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 148672-09-7.mol
• Article Data: 24

Chemical Properties

• Melting Point: 195-197°C
• Boiling Point: 530.9°Cat760mmHg
• Flash Point: 274.9°C
• Appearance: /
• Density: 1.314g/cm³
• Vapor Pressure: 2.35E-11mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: −20°C
• Solubility: DMSO, Ethanol, Methanol
• PKA: 8.86±0.70(Predicted)
• CAS DataBase Reference: ESTRONE 3-O-SULFAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: ESTRONE 3-O-SULFAMATE(148672-09-7)
• EPA Substance Registry System: ESTRONE 3-O-SULFAMATE(148672-09-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 148672-09-7(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Crystalline Solid

Uses

Different sources of media describe the Uses of 148672-09-7 differently. You can refer to the following data:
1. A potent inhibitor of estrone sulfatase. Inhibits estrone sulfatase >99% at 0.1uM in intact MCF-7 cells, IC50=65pM
2. A potent inhibitor of estrone sulfatase. Inhibits estrone sulfatase >99% at 0.1uM in intact MCF-7 cells, IC50=65pM.

Purification Methods

Estrone 3-O-sulfamate [148672-09-7] M 349.5. Estrone 3-O-sulfamate is purified by silica gel flash chromatography to give a product with one spot on TLC. It is an active site-directed inhibitor of estrone sulfatase, i.e. a time-dependent enzyme inactivator. [Woo et al. J Med Chem 39 1349 1996, Purohit et al. Biochemistry 34 11508 1995.]

InChI:InChI=1/C18H23NO4S/c1-18-9-8-14-13-5-3-12(23-24(19,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16H,2,4,6-9H2,1H3,(H2,19,21,22)/t14-,15-,16+,18+/m1/s1

Upstream product

• 1189-71-5 isocyanate de chlorosulfonyle 
• 53-16-7 Estrone 

Downstream Products

• 53-16-7 Estrone 
• 172377-52-5 estradiol 3-sulphamate 

Relevant articles and documents

Oestrone 3-O-(N-acetyl)sulphamate, a potential molecular probe of the active site of oestrone sulphatase

N,N-Dialkylated derivatives of the steroid sulphatase inhibitor, oestrone 3-O-sulphamate (EMATE) are weak reversible inhibitors of the enzyme. N-Acetylated-EMATE (8), but not the benzoyl derivative, inhibits the enzyme irreversibly, albeit less potently than EMATE and will allow hitherto difficult radiolabelling on the sulphamate group to facilitate investigation of the enzyme inactivation mechanism.

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.

Efficient synthesis of N-oxysulfonyl formamidines through thionyl chloride-promoted reaction of sulfamates with formamides

N-Oxysulfonyl formamidine derivatives have been efficiently synthesized under mild conditions through direct condensation of various sulfamates and formamides in the presence of thionyl chloride. The scope of this reaction was investigated, and a plausible mechanism was proposed. The resulting N-oxysulfonyl formamidines can be converted to sulfamates through appropriate deprotection.

Hexafluoroisopropyl sulfamate: A useful reagent for the synthesis of sulfamates and sulfamides

Sulfamates and sulfamides are most often synthesized from alcohols and amines with sulfamoyl chloride, which is an unstable reagent. We have identified hexafluoroisopropyl sulfamate (HFIPS) as a bench-stable solid that reacts readily with a wide variety of alcohols, amines, phenols, and anilines under mild reaction conditions. The sole byproduct of the reaction is hexafluoroisopropanol (HFIP) and reaction products can often be isolated in high purity after an aqueous workup (optional) and removal of solvents by evaporation.