(9beta,13alpha,14beta,17alpha)-2-Methoxyestra-1,3,5(10)-Triene-3,17-Diyl Disulfamate

Base Information

Chemical Name:(9beta,13alpha,14beta,17alpha)-2-Methoxyestra-1,3,5(10)-Triene-3,17-Diyl Disulfamate
CAS No.:401600-86-0
Molecular Formula:C₁₉H₂₈N₂O₇S₂
Molecular Weight:460.573
Hs Code.:
UNII:S57SQE6LE5
DSSTox Substance ID:DTXSID501336467
Nikkaji Number:J1.971.840I
Wikipedia:2-Methoxyestradiol_disulfamate
Wikidata:Q27097624
Pharos Ligand ID:S417NCHA2JS7
Metabolomics Workbench ID:151552
ChEMBL ID:CHEMBL218382

Synonyms:2-methoxyestradiol-3,17-O,O-bis(sulfamate);2-methoxyestradiol-3,17-O,O-bis-sulfamate;3,17beta-bis-sulfamoyloxy-2-methoxyestra-1,3,5(10)-triene;STX 140;STX-140;STX140

Suppliers and Price of (9beta,13alpha,14beta,17alpha)-2-Methoxyestra-1,3,5(10)-Triene-3,17-Diyl Disulfamate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Cayman Chemical
10mg
$ 472.00

Cayman Chemical
STX140
5mg
$ 266.00

Cayman Chemical
STX140
1mg
$ 59.00

Total 2 raw suppliers

Chemical Property of (9beta,13alpha,14beta,17alpha)-2-Methoxyestra-1,3,5(10)-Triene-3,17-Diyl Disulfamate

Chemical Property:

PSA：0.00000
LogP:0.00000
XLogP3:2.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:5
Exact Mass:460.13379358
Heavy Atom Count:30
Complexity:853

Purity/Quality:

99% ^*data from raw suppliers

^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC12CCC3C(C1CCC2OS(=O)(=O)N)CCC4=CC(=C(C=C34)OC)OS(=O)(=O)N
Isomeric SMILES:C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OS(=O)(=O)N)CCC4=CC(=C(C=C34)OC)OS(=O)(=O)N
Description STX140 is an estrogen sulfamate with anticancer activities. It inhibits steroid sulfatase with IC50 values of 39 and 0.5 nM in placental microsomes and MCF-7 cancer cells, respectively. STX140 also binds to carbonic anhydrase IX and II (Kis = 70 and 270 nM, respectively). It inhibits bovine brain tubulin assembly in a cell-free assay (IC50 = 2.2 μM) and tubule formation in human umbilical vein epithelial cells (HUVECs) when used at concentrations of 50 and 100 nM. STX140 inhibits proliferation of LNCaP, PC3, and MDA-MB-231 cancer cells, as well as wild-type A2780 cancer cells and adriamycin- and cisplatin-resistant A2780 cancer cells (IC50s = 530, 400, 618, 330, 870, and 380 nM, respectively). It reduces angiogenesis in a Matrigel? plug assay in mice and tumor growth in MCF-7 and MDA-MB-231 mouse xenograft models when used at a dose of 20 mg/kg.

Technology Process of (9beta,13alpha,14beta,17alpha)-2-Methoxyestra-1,3,5(10)-Triene-3,17-Diyl Disulfamate

There total 6 articles about (9beta,13alpha,14beta,17alpha)-2-Methoxyestra-1,3,5(10)-Triene-3,17-Diyl Disulfamate 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: 90.0%

: 362-07-2
2-Methoxyestradiol

: 401600-86-0
2-methoxyestradiol 3,17-O,O-bis-sulfamate

Guidance literature:: With sulphamoyl chloride; In ISOPROPYLAMIDE; at 0 - 20 ℃; for 1.5h;
DOI:10.1002/jlcr.1930

Reference yield: 74.0%

: 362-07-2
2-Methoxyestradiol

: 7778-42-9
sulphamoyl chloride

: 401600-86-0
2-methoxyestradiol 3,17-O,O-bis-sulfamate

Guidance literature:: With 5-(N,N-dimethyl)amiloride hydrochloride; at 0 - 20 ℃;
DOI:10.1016/j.steroids.2012.04.007

Reference yield:

: 50-28-2
estradiol

: 401600-86-0
2-methoxyestradiol 3,17-O,O-bis-sulfamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Reflux

2.1: sec.-butyllithium / tetrahydrofuran / -78 °C

2.2: -78 - 20 °C

2.3: 20 °C

3.1: tetra-(n-butyl)ammonium iodide; potassium carbonate / N,N-dimethyl-formamide / 20 °C

4.1: hydrogenchloride / tetrahydrofuran; water / 20 °C

5.1: 5-(N,N-dimethyl)amiloride hydrochloride / 0 - 20 °C

With hydrogenchloride; sec.-butyllithium; tetra-(n-butyl)ammonium iodide; potassium carbonate; N-ethyl-N,N-diisopropylamine; 5-(N,N-dimethyl)amiloride hydrochloride; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1016/j.steroids.2012.04.007