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288628-05-7,MFCD11111143
Catalog No.:AA002WT4

288628-05-7 | Sulfamic acid, 6,7,8,9,10,11-hexahydro-6-oxobenzo[b]cyclohepta[d]pyran-3-yl ester

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1mg
98%
in stock  
$15.00   $11.00
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10mg
98%
in stock  
$68.00   $48.00
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25mg
98%
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$134.00   $94.00
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50mg
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$228.00   $160.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA002WT4
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
SMILES:
O=c1oc2cc(ccc2c2c1CCCCC2)OS(=O)(=O)N
Properties
Properties
 
Form:
Solid  

Computed Properties
 
Complexity:
562  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
2  
XLogP3:
2.3  

Downstream Synthesis Route
CASUnavailable 
  288628-05-7   
CASUnavailable 

[1]Locationinpatent:schemeortableWoo,L.W.Lawrence;Ganeshapillai,Dharshini;Thomas,MarkP.;Sutcliffe,OliverB.;Malini,Bindu;Mahon,MaryF.;Purohit,Atul;Potter,BarryV.L.[ChemMedChem,2011,vol.6,#11,p.2019-2034]

[1]Locationinpatent:experimentalpartWoo,L.W.Lawrence;Ganeshapillai,Dharshini;Thomas,MarkP.;Sutcliffe,OliverB.;Malini,Bindu;Mahon,MaryF.;Purohit,Atul;Potter,BarryV.L.[ChemMedChem,2011,vol.6,#11,p.2019-2034]

[1]CurrentPatentAssignee:IPSENSA-US2012/321714,2012,A1Locationinpatent:Page/Pagecolumn12

Literature

Title: Synthesis, structure-activity relationship of iodinated-4-aryloxymethyl-coumarins as potential anti-cancer and anti-mycobacterial agents.

Journal: European journal of medicinal chemistry 20140303

Title: Naturally occurring steroids in Xenopus oocyte during meiotic maturation. Unexpected presence and role of steroid sulfates.

Journal: Molecular and cellular endocrinology 20121015

Title: 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.

Journal: Biochemical pharmacology 20121015

Title: In vitro evaluation of the interaction potential of irosustat with drug-metabolizing enzymes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20120701

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: 17β-Arylsulfonamides of 17β-aminoestra-1,3,5(10)-trien-3-ol as highly potent inhibitors of steroid sulfatase.

Journal: Bioorganic & medicinal chemistry 20120215

Title: Structure-activity relationship for the first-in-class clinical steroid sulfatase inhibitor Irosustat (STX64, BN83495).

Journal: ChemMedChem 20111104

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

Journal: Bioorganic & medicinal chemistry 20111015

Title: In vitro metabolism of irosustat, a novel steroid sulfatase inhibitor: interspecies comparison, metabolite identification, and metabolic enzyme identification.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20110701

Title: Irosustat: a first-generation steroid sulfatase inhibitor in breast cancer.

Journal: Expert review of anticancer therapy 20110201

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

Journal: Journal of medicinal chemistry 20100311

Title: The use of steroid sulfatase inhibitors as a novel therapeutic strategy against hormone-dependent endometrial cancer.

Journal: Endocrinology 20080801

Title: Chiral aromatase and dual aromatase-steroid sulfatase inhibitors from the letrozole template: synthesis, absolute configuration, and in vitro activity.

Journal: Journal of medicinal chemistry 20080724

Title: Inactivation of recombinant human steroid sulfatase by KW-2581.

Journal: The Journal of steroid biochemistry and molecular biology 20080101

Title: Inhibition of steroid sulphatase activity via the percutaneous route: a new option for breast cancer therapy.

Journal: Anticancer research 20080101

Title: A novel steroidal selective steroid sulfatase inhibitor KW-2581 inhibits sulfated-estrogen dependent growth of breast cancer cells in vitro and in animal models.

Journal: Breast cancer research and treatment 20071201

Title: 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.

Journal: Breast cancer research and treatment 20070801

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

Journal: Journal of medicinal chemistry 20070726

Title: Dual aromatase-steroid sulfatase inhibitors.

Journal: Journal of medicinal chemistry 20070726

Title: Steroid sulfatase: a new target for the endocrine therapy of breast cancer.

Journal: The oncologist 20070401

Title: 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.

Journal: Anticancer research 20070101

Title: Hormonal therapy: still much to learn.

Journal: Clinical breast cancer 20060601

Title: Phase I study of STX 64 (667 Coumate) in breast cancer patients: the first study of a steroid sulfatase inhibitor.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20060301

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

Journal: Endocrine reviews 20050401

Title: Crystal structure of human carbonic anhydrase II at 1.95 A resolution in complex with 667-coumate, a novel anti-cancer agent.

Journal: The Biochemical journal 20050201

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

Journal: Biochemical and biophysical research communications 20040910

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: Steroid sulphatase inhibitors for breast cancer therapy.

Journal: The Journal of steroid biochemistry and molecular biology 20030901

Title: First dual aromatase-steroid sulfatase inhibitors.

Journal: Journal of medicinal chemistry 20030717

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

Journal: Bioorganic & medicinal chemistry letters 20030310

Title: In vitro and in vivo models for the evaluation of new inhibitors of human steroid sulfatase, devoid of residual estrogenic activity.

Journal: The Journal of steroid biochemistry and molecular biology 20030201

Title: Development of a sensitive high-performance liquid chromatography method for the detection of 667 COUMATE in vivo.

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

Journal: Molecular and cellular endocrinology 20010122

Title: Purohit A, et al. In vivo inhibition of estrone sulfatase activity and growth of nitrosomethylurea-induced mammary tumors by 667 COUMATE. Cancer Res. 2000 Jul 1;60(13):3394-6.

Title: Raobaikady B, et al. Inhibition of MCF-7 breast cancer cell proliferation and in vivo steroid sulphatase activity by 2-methoxyoestradiol-bis-sulphamate. J Steroid Biochem Mol Biol. 2003 Feb;84(2-3):351-8.

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Tags:288628-05-7 Molecular Formula|288628-05-7 MDL|288628-05-7 SMILES|288628-05-7 Sulfamic acid, 6,7,8,9,10,11-hexahydro-6-oxobenzo[b]cyclohepta[d]pyran-3-yl ester