Emate

Base Information

• Chemical Name: Emate
• CAS No.: 148672-09-7
• Molecular Formula: C18H23 N O4 S
• Molecular Weight: 349.451
• NSC Number: 685426
• DSSTox Substance ID: DTXSID20933447
• Nikkaji Number: J574.495D
• Wikipedia: Estrone_sulfamate
• Wikidata: Q82909260
• Pharos Ligand ID: 7XJZM7GRT6YM
• ChEMBL ID: CHEMBL122708
• Mol file: 148672-09-7.mol

Synonyms:EMATE compound;estra-1,3,5(10)-trien-17-one-3-sulfamate;estrone-3-O-sulfamate;oestrone-3-O-sulphamate

Chemical Property of Emate

Chemical Property:

• Vapor Pressure: 2.35E-11mmHg at 25°C
• Melting Point: 195-197°C
• Boiling Point: 530.9°Cat760mmHg
• PKA: 8.86±0.70(Predicted)
• Flash Point: 274.9°C
• PSA: 94.84000
• Density: 1.314g/cm³
• LogP: 4.47520
• Storage Temp.: −20°C
• Solubility.: DMSO, Ethanol, Methanol
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 349.13477939
• Heavy Atom Count: 24
• Complexity: 627

Purity/Quality:

99% ^*data from raw suppliers

Estrone3-O-Sulfamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)OS(=O)(=O)N
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)OS(=O)(=O)N
• Uses: A potent inhibitor of estrone sulfatase. Inhibits estrone sulfatase >99% at 0.1uM in intact MCF-7 cells, IC50=65pM A potent inhibitor of estrone sulfatase. Inhibits estrone sulfatase >99% at 0.1uM in intact MCF-7 cells, IC50=65pM.

Technology Process of Emate

There total 7 articles about Emate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

Estrone (53-16-7) → estrone 3-O-sulfamate (148672-09-7)

Guidance literature:

With sulphamoyl chloride; In 1-methyl-pyrrolidin-2-one; at 0 - 20 ℃; for 3h;

DOI:10.1016/S0040-4039(00)01130-8

Reference yield: 96.0%

(polystyrene resin Novabiochem)-C6H4(C6H5)2CNHSO2O-3-estrone → estrone 3-O-sulfamate (148672-09-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 12h;

DOI:10.1021/ol990381p

Reference yield: 85.0%

(E)-(13S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl[(dimethylamino)methylene]sulfamate → estrone 3-O-sulfamate (148672-09-7)

Guidance literature:

With hydrazine hydrate; In ethanol; at 20 ℃; for 1h;

DOI:10.1080/00397911.2017.1361999

upstream raw materials:

Estrone

isocyanate de chlorosulfonyle

Downstream raw materials:

estradiol 3-sulphamate

Estrone

Refernces

• 1、 Woo, L. W. Lawrence,Howarth, Nicola M.,Purohit, Atul,Hejaz, Hatem A. M.,Reed, Michael J.,Potter, Barry V. L.. "Steroidal and nonsteroidal sulfamates as potent inhibitors of steroid sulfatase". . p. 1068 - 1083. Retrieved 1998.
• 2、 Fr?hlich, Tony,Mai, Christina,Bogautdinov, Roman P.,Morozkina, Svetlana N.,Shavva, Alexander G.,Friedrich, Oliver,Gilbert, Daniel F.,Tsogoeva, Svetlana B.. "Synthesis of Tamoxifen-Artemisinin and Estrogen-Artemisinin Hybrids Highly Potent Against Breast and Prostate Cancer". . p. 1473 - 1479. Retrieved 2020.
• 3、 Sguazzin, Matthew A.,Johnson, Jarrod W.,Magolan, Jakob. "Hexafluoroisopropyl sulfamate: A useful reagent for the synthesis of sulfamates and sulfamides". supporting information. p. 3373 - 3378. Retrieved 2021/05/10.