Home Other Building Blocks Sulfamic acid, 6,7,8,9,10,11-hexahydro-6-oxobenzo[b]cyclohepta[d]pyran-3-yl ester

Sulfamic acid, 6,7,8,9,10,11-hexahydro-6-oxobenzo[b]cyclohepta[d]pyran-3-yl ester

CAS No.:
288628-05-7
Catalog Number:
AG002WVW
Molecular Formula:
C14H15NO5S
Molecular Weight:
309.3376
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
99%
1 week
United States
$182
- +
10mg
99%
1 week
United States
$265
- +
25mg
99%
1 week
United States
$501
- +
50mg
99%
1 week
United States
$807
- +
100mg
99%
1 week
United States
$1362
- +
Product Description
Catalog Number:
AG002WVW
Chemical Name:
Sulfamic acid, 6,7,8,9,10,11-hexahydro-6-oxobenzo[b]cyclohepta[d]pyran-3-yl ester
CAS Number:
288628-05-7
Molecular Formula:
C14H15NO5S
Molecular Weight:
309.3376
MDL Number:
MFCD11111143
IUPAC Name:
(6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta[c]chromen-3-yl) sulfamate
InChI:
InChI=1S/C14H15NO5S/c15-21(17,18)20-9-6-7-11-10-4-2-1-3-5-12(10)14(16)19-13(11)8-9/h6-8H,1-5H2,(H2,15,17,18)
InChI Key:
DSLPMJSGSBLWRE-UHFFFAOYSA-N
SMILES:
O=c1oc2cc(ccc2c2c1CCCCC2)OS(=O)(=O)N
UNII:
366037O6O7
Properties
Complexity:
562  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
309.067g/mol
Formal Charge:
0
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
309.336g/mol
Monoisotopic Mass:
309.067g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
104A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.3  
Literature
Title Journal
Synthesis, structure-activity relationship of iodinated-4-aryloxymethyl-coumarins as potential anti-cancer and anti-mycobacterial agents. European journal of medicinal chemistry 20140303
Naturally occurring steroids in Xenopus oocyte during meiotic maturation. Unexpected presence and role of steroid sulfates. Molecular and cellular endocrinology 20121015
Enhanced expression of organic anion transporting polypeptides (OATPs) in androgen receptor-positive prostate cancer cells: possible role of OATP1A2 in adaptive cell growth under androgen-depleted conditions. Biochemical pharmacology 20121015
In vitro evaluation of the interaction potential of irosustat with drug-metabolizing enzymes. Drug metabolism and disposition: the biological fate of chemicals 20120701
Proton-in-flight mechanism for the spontaneous hydrolysis of N-methyl O-phenyl sulfamate: implications for the design of steroid sulfatase inhibitors. The Journal of organic chemistry 20120504
17β-Arylsulfonamides of 17β-aminoestra-1,3,5(10)-trien-3-ol as highly potent inhibitors of steroid sulfatase. Bioorganic & medicinal chemistry 20120215
Structure-activity relationship for the first-in-class clinical steroid sulfatase inhibitor Irosustat (STX64, BN83495). ChemMedChem 20111104
Inhibition of steroid sulfatase with 4-substituted estrone and estradiol derivatives. Bioorganic & medicinal chemistry 20111015
In vitro metabolism of irosustat, a novel steroid sulfatase inhibitor: interspecies comparison, metabolite identification, and metabolic enzyme identification. Drug metabolism and disposition: the biological fate of chemicals 20110701
Irosustat: a first-generation steroid sulfatase inhibitor in breast cancer. Expert review of anticancer therapy 20110201
Highly potent first examples of dual aromatase-steroid sulfatase inhibitors based on a biphenyl template. Journal of medicinal chemistry 20100311
The use of steroid sulfatase inhibitors as a novel therapeutic strategy against hormone-dependent endometrial cancer. Endocrinology 20080801
Chiral aromatase and dual aromatase-steroid sulfatase inhibitors from the letrozole template: synthesis, absolute configuration, and in vitro activity. Journal of medicinal chemistry 20080724
Inactivation of recombinant human steroid sulfatase by KW-2581. The Journal of steroid biochemistry and molecular biology 20080101
Inhibition of steroid sulphatase activity via the percutaneous route: a new option for breast cancer therapy. Anticancer research 20080101
A novel steroidal selective steroid sulfatase inhibitor KW-2581 inhibits sulfated-estrogen dependent growth of breast cancer cells in vitro and in animal models. Breast cancer research and treatment 20071201
Inhibition of steroid sulfatase activity and cell proliferation in ZR-75-1 and BT-474 human breast cancer cells by KW-2581 in vitro and in vivo. Breast cancer research and treatment 20070801
Thiosemicarbazones of formyl benzoic acids as novel potent inhibitors of estrone sulfatase. Journal of medicinal chemistry 20070726
Dual aromatase-steroid sulfatase inhibitors. Journal of medicinal chemistry 20070726
Steroid sulfatase: a new target for the endocrine therapy of breast cancer. The oncologist 20070401
Measurement of estrone sulfate in postmenopausal women: comparison of direct RIA and GC-MS/MS methods for monitoring response to endocrine therapy in women with breast cancer. Anticancer research 20070101
Hormonal therapy: still much to learn. Clinical breast cancer 20060601
Phase I study of STX 64 (667 Coumate) in breast cancer patients: the first study of a steroid sulfatase inhibitor. Clinical cancer research : an official journal of the American Association for Cancer Research 20060301
Steroid sulfatase: molecular biology, regulation, and inhibition. Endocrine reviews 20050401
Crystal structure of human carbonic anhydrase II at 1.95 A resolution in complex with 667-coumate, a novel anti-cancer agent. The Biochemical journal 20050201
Pharmacokinetics of the nonsteroidal steroid sulphatase inhibitor 667 COUMATE and its sequestration into red blood cells in rats. British journal of cancer 20041004
The role of steroid sulphatase in regulating the oestrogenicity of oestrogen sulphamates. Biochemical and biophysical research communications 20040910
Inhibition of estrone sulfatase (ES) by alkyl and cycloalkyl ester derivatives of 4-[(aminosulfonyl)oxy] benzoic acid. Bioorganic & medicinal chemistry letters 20040209
Steroid sulphatase inhibitors for breast cancer therapy. The Journal of steroid biochemistry and molecular biology 20030901
First dual aromatase-steroid sulfatase inhibitors. Journal of medicinal chemistry 20030717
Docking studies of sulphamate inhibitors of estrone sulphatase in human carbonic anhydrase II. Bioorganic & medicinal chemistry letters 20030310
In vitro and in vivo models for the evaluation of new inhibitors of human steroid sulfatase, devoid of residual estrogenic activity. The Journal of steroid biochemistry and molecular biology 20030201
Development of a sensitive high-performance liquid chromatography method for the detection of 667 COUMATE in vivo. The Journal of steroid biochemistry and molecular biology 20030201
Inhibition of MCF-7 breast cancer cell proliferation and in vivo steroid sulphatase activity by 2-methoxyoestradiol-bis-sulphamate. The Journal of steroid biochemistry and molecular biology 20030201
Design, synthesis and biochemical evaluation of AC ring mimics as novel inhibitors of the enzyme estrone sulfatase (ES). The Journal of steroid biochemistry and molecular biology 20021101
Design, synthesis and biochemical evaluation of AC ring mimics as novel inhibitors of the enzyme estrone sulfatase (ES). Bioorganic & medicinal chemistry letters 20020520
Determination and use of a transition state for the enzyme estrone sulfatase (ES) from a proposed reaction mechanism. Bioorganic & medicinal chemistry letters 20011203
Non-steroidal and steroidal sulfamates: new drugs for cancer therapy. Molecular and cellular endocrinology 20010122
Properties