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148672-09-7,MFCD11045571
Catalog No.:AA006TW8

148672-09-7 | Estrone 3-O-Sulfamate

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1mg
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5mg
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10mg
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25mg
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50mg
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100mg
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  • Technical Information
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  • Literature
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA006TW8
Chemical Name:
Estrone 3-O-Sulfamate
CAS Number:
148672-09-7
Molecular Formula:
C18H23NO4S
Molecular Weight:
349.4445
MDL Number:
MFCD11045571
SMILES:
O=C1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)OS(=O)(=O)N
NSC Number:
685426
Properties
Properties
 
Form:
Solid  
MP:
192-194°C  
Storage:
-20 ℃;Keep in dry area;  

Computed Properties
 
Complexity:
627  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
2  
XLogP3:
2.4  

Literature

Title: Proton-in-flight mechanism for the spontaneous hydrolysis of N-methyl O-phenyl sulfamate: implications for the design of steroid sulfatase inhibitors.

Journal: The Journal of organic chemistry 20120504

Title: Characterization of steroid sulfatase in the MC3T3-E1 mouse pre-osteoblastic cell line.

Journal: Steroids 20120501

Title: Synthesis and evaluation of analogues of estrone-3-O-sulfamate as potent steroid sulfatase inhibitors.

Journal: Bioorganic & medicinal chemistry 20120415

Title: Structure-activity relationships for the interaction of 5,10-dihydroindeno[1,2-b]indole derivatives with human and bovine carbonic anhydrase isoforms I, II, III, IV and VI.

Journal: European journal of medicinal chemistry 20120301

Title: Inhibition of steroid sulfatase with 4-substituted estrone and estradiol derivatives.

Journal: Bioorganic & medicinal chemistry 20111015

Title: Direct effect of dehydroepiandrosterone sulfate (DHEAS) on PC-12 cell differentiation processes.

Journal: Molecular and cellular endocrinology 20110410

Title: [Steroid sulfatase inhibitor].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20100601

Title: Structures of human carbonic anhydrase II/inhibitor complexes reveal a second binding site for steroidal and nonsteroidal inhibitors.

Journal: Biochemistry 20100427

Title: Highly potent first examples of dual aromatase-steroid sulfatase inhibitors based on a biphenyl template.

Journal: Journal of medicinal chemistry 20100311

Title: Thiosemicarbazones of formyl benzoic acids as novel potent inhibitors of estrone sulfatase.

Journal: Journal of medicinal chemistry 20070726

Title: Tibolone and its delta-4, 7alpha-methyl norethisterone metabolite are reversible inhibitors of human aromatase.

Journal: The Journal of steroid biochemistry and molecular biology 20070501

Title: 2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.

Journal: Journal of medicinal chemistry 20061228

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

Journal: Steroids 20060501

Title: Carbonic anhydrase inhibitors: inhibition of the human isozymes I, II, VA, and IX with a library of substituted difluoromethanesulfonamides.

Journal: Bioorganic & medicinal chemistry letters 20051201

Title: Carbonic anhydrase inhibitors: stacking with Phe131 determines active site binding region of inhibitors as exemplified by the X-ray crystal structure of a membrane-impermeant antitumor sulfonamide complexed with isozyme II.

Journal: Journal of medicinal chemistry 20050908

Title: A-ring-substituted estrogen-3-O-sulfamates: potent multitargeted anticancer agents.

Journal: Journal of medicinal chemistry 20050811

Title: First crystal structures of human carbonic anhydrase II in complex with dual aromatase-steroid sulfatase inhibitors.

Journal: Biochemistry 20050510

Title: Pregnenolone sulphate attenuates AMPA cytotoxicity on rat cortical neurons.

Journal: The European journal of neuroscience 20050501

Title: Steroid sulfatase: molecular biology, regulation, and inhibition.

Journal: Endocrine reviews 20050401

Title: N-Acyl arylsulfonamides as novel, reversible inhibitors of human steroid sulfatase.

Journal: Bioorganic & medicinal chemistry letters 20050215

Title: The nature of inhibition of steroid sulphatase activity by tibolone and its metabolites.

Journal: The Journal of steroid biochemistry and molecular biology 20050201

Title: Anti-cancer activities of novel D-ring modified 2-substituted estrogen-3-O-sulfamates.

Journal: The Journal of steroid biochemistry and molecular biology 20050201

Title: Stilbene-based inhibitors of estrone sulfatase with a dual mode of action in human breast cancer cells.

Journal: Archiv der Pharmazie 20041201

Title: Pharmacokinetics of the nonsteroidal steroid sulphatase inhibitor 667 COUMATE and its sequestration into red blood cells in rats.

Journal: British journal of cancer 20041004

Title: Estrone formate: a novel type of irreversible inhibitor of human steroid sulfatase.

Journal: Bioorganic & medicinal chemistry letters 20041004

Title: The role of steroid sulphatase in regulating the oestrogenicity of oestrogen sulphamates.

Journal: Biochemical and biophysical research communications 20040910

Title: 2-(1-adamantyl)-4-(thio)chromenone-6-carboxylic acids: potent reversible inhibitors of human steroid sulfatase.

Journal: Journal of medicinal chemistry 20040812

Title: 2-Alkylsulfanyl estrogen derivatives: synthesis of a novel class of multi-targeted anti-tumour agents.

Journal: Bioorganic & medicinal chemistry letters 20040621

Title: Inhibition of in vitro angiogenesis by 2-methoxy- and 2-ethyl-estrogen sulfamates.

Journal: International journal of cancer 20040420

Title: Inhibition of estrone sulfatase (ES) by alkyl and cycloalkyl ester derivatives of 4-[(aminosulfonyl)oxy] benzoic acid.

Journal: Bioorganic & medicinal chemistry letters 20040209

Title: Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride.

Journal: Bioorganic & medicinal chemistry letters 20040119

Title: Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with EMATE, a dual inhibitor of carbonic anhydrases and steroid sulfatase.

Journal: Bioorganic & medicinal chemistry letters 20040105

Title: 6-(2-adamantan-2-ylidene-hydroxybenzoxazole)-O-sulfamate: a potent non-steroidal irreversible inhibitor of human steroid sulfatase.

Journal: Bioorganic & medicinal chemistry letters 20031215

Title: Nortropinyl-arylsulfonylureas as novel, reversible inhibitors of human steroid sulfatase.

Journal: Bioorganic & medicinal chemistry letters 20031103

Title: Development of novel steroid sulfatase inhibitors. I. Synthesis and biological evaluation of biphenyl-4-O-sulfamates.

Journal: The Journal of steroid biochemistry and molecular biology 20031101

Title: Inhibition of estrone sulfate-induced uterine growth by potent nonestrogenic steroidal inhibitors of steroid sulfatase.

Journal: Cancer research 20031001

Title: The design, synthesis, and in vitro biochemical evaluation of a series of esters of 4-[(aminosulfonyl)oxy]benzoate as novel and highly potent inhibitors of estrone sulfatase.

Journal: Biochemical and biophysical research communications 20030808

Title: Microtiter plate cellular assay for human steroid sulfatase with fluorescence readout.

Journal: Analytical biochemistry 20030715

Title: Inhibition of carbonic anhydrase II by steroidal and non-steroidal sulphamates.

Journal: Biochemical and biophysical research communications 20030613

Title: Carbonic anhydrase inhibitors. Inhibition of cytosolic isozymes I and II and transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors.

Journal: Journal of medicinal chemistry 20030522

Title: D-ring modified estrone derivatives as novel potent inhibitors of steroid sulfatase.

Journal: Bioorganic & medicinal chemistry 20030417

Title: Docking studies of sulphamate inhibitors of estrone sulphatase in human carbonic anhydrase II.

Journal: Bioorganic & medicinal chemistry letters 20030310

Title: Novel D-ring modified steroid derivatives as potent, non-estrogenic, steroid sulfatase inhibitors with in vivo activity.

Journal: The Journal of steroid biochemistry and molecular biology 20030201

Title: Inhibition of MCF-7 breast cancer cell proliferation and in vivo steroid sulphatase activity by 2-methoxyoestradiol-bis-sulphamate.

Journal: The Journal of steroid biochemistry and molecular biology 20030201

Title: Design, synthesis and biochemical evaluation of AC ring mimics as novel inhibitors of the enzyme estrone sulfatase (ES).

Journal: The Journal of steroid biochemistry and molecular biology 20021101

Title: 2-Substituted 4-(thio)chromenone 6-O-sulfamates: potent inhibitors of human steroid sulfatase.

Journal: Journal of medicinal chemistry 20020912

Title: Inhibition of estrone sulfatase (ES) by derivatives of 4-[(aminosulfonyl)oxy] benzoic acid.

Journal: Bioorganic & medicinal chemistry letters 20020902

Title: Inhibition of steryl sulfatase activity in LNCaP human prostate cancer cells.

Journal: Steroids 20020901

Title: 4,4'-Benzophenone-O,O'-disulfamate: a potent inhibitor of steroid sulfatase.

Journal: Bioorganic & medicinal chemistry letters 20020819

Title: The design, synthesis, and biochemical evaluation of derivatives of biphenyl sulfamate-based compounds as novel inhibitors of estrone sulfatase.

Journal: Biochemical and biophysical research communications 20020531

Title: A novel type of nonsteroidal estrone sulfatase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20020520

Title: Design, synthesis and biochemical evaluation of AC ring mimics as novel inhibitors of the enzyme estrone sulfatase (ES).

Journal: Bioorganic & medicinal chemistry letters 20020520

Title: The mechanism of the irreversible inhibition of estrone sulfatase (ES) through the consideration of a range of methane- and amino-sulfonate-based compounds.

Journal: Bioorganic & medicinal chemistry letters 20020506

Title: Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES).

Journal: The Journal of steroid biochemistry and molecular biology 20020401

Title: Nonsteroidal compounds designed to mimic potent steroid sulfatase inhibitors.

Journal: The Journal of steroid biochemistry and molecular biology 20020301

Title: Determination and use of a transition state for the enzyme estrone sulfatase (ES) from a proposed reaction mechanism.

Journal: Bioorganic & medicinal chemistry letters 20011203

Title: Steroid sulfatase in the human hair follicle concentrates in the dermal papilla.

Journal: The Journal of investigative dermatology 20011201

Title: Tibolone: a compound with tissue specific inhibitory effects on sulfatase.

Journal: Molecular and cellular endocrinology 20011025

Title: Hydrophobicity, a physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES).

Journal: Bioorganic & medicinal chemistry letters 20010917

Title: Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES).

Journal: Bioorganic & medicinal chemistry letters 20010409

Title: Novel inhibitors of the enzyme estrone sulfatase (ES).

Journal: Bioorganic & medicinal chemistry letters 20010326

Title: Non-steroidal and steroidal sulfamates: new drugs for cancer therapy.

Journal: Molecular and cellular endocrinology 20010122

Title: Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group.

Journal: European journal of medicinal chemistry 20010101

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