217792-89-7

Basic information

• Product Name: 2-HYDROXY-3,17?-O-BIS(METHOXYMETHYL)ESTRADIOL
• Synonyms: 2-HYDROXY-3,17?-O-BIS(METHOXYMETHYL)ESTRADIOL;(17)-3,17-Bis(methoxymethoxy)estra-1,3,5(10)-trien-2-ol
• CAS NO: 217792-89-7
• Molecular Formula: C₂₂H₃₂O₅
• Molecular Weight: 376.48648
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 217792-89-7.mol

Chemical Properties

• Boiling Point: 494.374°C at 760 mmHg
• Flash Point: 252.788°C
• Appearance: /
• Density: 1.182g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.561
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• PKA: 9.52±0.60(Predicted)
• CAS DataBase Reference: 2-HYDROXY-3,17?-O-BIS(METHOXYMETHYL)ESTRADIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY-3,17?-O-BIS(METHOXYMETHYL)ESTRADIOL(217792-89-7)
• EPA Substance Registry System: 2-HYDROXY-3,17?-O-BIS(METHOXYMETHYL)ESTRADIOL(217792-89-7)

Safety Data

• Hazardous Substances Data: 217792-89-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-HYDROXY-3,17?-O-BIS(METHOXYMETHYL)ESTRADIOL is used as an intermediate compound for the synthesis of various organic compounds. Its unique structure allows it to be a versatile building block in the creation of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-HYDROXY-3,17?-O-BIS(METHOXYMETHYL)ESTRADIOL is used as a key component in the development of new drugs, particularly those targeting hormonal imbalances or related conditions. Its chemical properties make it a valuable asset in the design and synthesis of novel therapeutic agents.
Used in Research and Development:
2-HYDROXY-3,17?-O-BIS(METHOXYMETHYL)ESTRADIOL is also utilized in research and development settings, where it serves as a valuable tool for understanding the structure-activity relationships of various biologically active molecules. Its unique chemical properties enable scientists to explore new avenues in drug discovery and development.
Used in Chemical Analysis:
In the field of chemical analysis, 2-HYDROXY-3,17?-O-BIS(METHOXYMETHYL)ESTRADIOL can be employed as a reference compound or standard for the calibration of analytical instruments and methods. Its distinct chemical characteristics make it suitable for validating the performance of various analytical techniques, ensuring accurate and reliable results in chemical measurements.

InChI:InChI=1/C22H32O5/c1-22-9-8-15-16(18(22)6-7-21(22)27-13-25-3)5-4-14-10-20(26-12-24-2)19(23)11-17(14)15/h10-11,15-16,18,21,23H,4-9,12-13H2,1-3H3/t15-,16+,18-,21-,22-/m0/s1

Upstream product

• 6599-97-9 2-formylestradiol 
• 50-28-2 estradiol 
• 113680-55-0 (8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene 
• 123715-80-0 (8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2-carbaldehyde 

Downstream Products

• 401600-86-0 2-methoxyestradiol 3,17-O,O-bis-sulfamate 
• 22145-26-2 (17β)-2-benzyloxy-1,3,5(10)-estratriene-3,17-diol 
• 1356544-09-6 2-hydroxyestradiol-3,17β-O,O-bis(N-trityl)sulfamate 
• 1356544-08-5 2-O-benzyloxyestradiol-3,17β-O,O-bis(N-trutyl)sulfamate 
• 1356544-11-0 2-O-benzyloxyestradiol-3,17β-O,O-bissulfamate 
• 1356544-07-4 2-O-benzyloxyestradiol-3,17β-O,O-bis(methoxymethyl)ether 
• 791595-66-9 3-benzyloxy-2-methoxy-17α-trifluoromethyl-1,3,5(10)-estratriene-17β-trimethylsilane 
• 26357-07-3 3-(benzyloxy)-2-methoxyestra-1,3,5⁽¹⁰⁾-trien-17-one 
• 362-08-3 2-methoxyestrone 

Relevant articles and documents

An optimized synthesis of 2-methoxyestradiol, a naturally occurring human metabolite with anticancer activity

2-Methoxyestradiol, a naturally occurring human metabolite with demonstrated anticancer activity, has been synthesized in three steps and 76% yield from the bis(MOM) ether of 2-formylestradiol.

Synthesis of 2-[11C]methoxy-3,17β-O,O-bis(sulfamoyl) estradiol as a new potential PET agent for imaging of steroid sulfatase (STS) in cancers

Steroid sulfatase (STS) catalyzes the hydrolysis of steroid sulfates to estrones, the main source of estrogens in tumors. Carbonic anhydrase II (CAII) is highly expressed in red blood cells through a coordination of the monoanionic form of the sulfamate moiety to the zinc atom in the enzyme active site, and CAII is highly expressed in several tumors. 2-Methoxy-3,17β-O,O- bis(sulfamoyl)estradiol (5) is a dual-function STS-CAII inhibitor inhibited STS with 39 nM IC50 value selectively over CAII with 379 nM IC 50 value. This compound exhibited potent antiproferative activity with mean graph midpoint value of 87 nM in the NCI 60-cell-line panel, and antiangiogenic in vitro and in vivo activity in an early-stage Lewis lung model as well. The compound has been recently developed as a multitargeted anticancer agent. Both STS and CAII are over-expressed in cancers and have become attractive targets for cancer treatment and molecular imaging of cancer. Here we report the first design and synthesis of 2-[11C]methoxy-3,17β- O,O-bis(sulfamoyl)estradiol ([11C]5) as a new potential imaging agent for biomedical imaging technique positron emission tomography (PET) to image STS in cancers. The authentic standard 5 was synthesized from 17β-estradiol by published procedures in 5 steps with 40% overall chemical yield. The precursor 2-hydroxy-3,17β-O,O-bis(sulfamoyl)estradiol (14a) for radiolabeling was synthesized from 17β-estradiol in 10 steps with 5% overall chemical yield. The target tracer [11C]5 was prepared from the precursor 14a with [11C]CH3OTf through O-[ 11C]methylation and isolated by HPLC combined with solid-phase extraction (SPE) purification in 40-50% radiochemical yields based on [ 11C]CO2 and decay corrected to end of bombardment (EOB), with 370-740 GBq/μmol specific activity at EOB.

Ortho-Formylation of estrogens. Synthesis of the anti-cancer agent 2-methoxyestradiol

Several estrogens were mono-formylated using a mixture of paraformaldehyde, MgCl2, and Et3N in refluxing THF. In all cases, the 2-isomer was formed as the major product with high regioselectivity compared to the 4-isomer. Excellent to high yields were obtained in all examples except one. The method was applied for an efficient synthesis of the anti-cancer agent 2-methoxyestradiol.

Synthesis and in vitro evaluation of 2-[11C]methoxyestradiol-3, 17β-O,O-bissulfamate for in vivo studies of angiogenesis

In the present study, 2-methoxyestradiol-3,17β-O,O-bissulfamate (1), a known angiogenesis inhibitor, was prepared in a radiolabeled form by 11C-methylation of 2-hydroxyestradiol-3,17β-O,O-bis(N-trityl) sulfamate (6) followed by detritylation. S

Synthesis of 2-[11C]methoxy-3,17β-estradiol to measure the pharmacokinetics of an antitumor drug candidate, 2-methoxy-3,17β-estradiol

2-Methoxy-3,17β-estradiol, an endogenous estrogen metabolite, showed cytotoxicity in various cancer cell lines and also has antiangiogenic and proapoptotic activities. Clinical I and II trials of 2-methoxy-3,17β- estradiol for multiple myeloma, advanced solid tumors, metastatic breast and prostate cancer are underway. We prepared 2-[11C]methoxy-3,17β- estradiol to measure the pharmacokinetics and organ distribution of 2-methoxy-3,17β-estradiol in clinical trials. 2-[11C]Methoxy-3, 17β-estradiol was synthesized from a precursor, 2-hydroxy-3,17β-O- bis(methoxymethyl)estradiol, in two steps with over 99% radiochemical purity. The overall reaction time was 45 min and the decay-corrected radiochemical yield was 32.9%. The distribution coefficient (logP7.4) of 2-[ 11C]methoxy-3,17β-estradiol at pH 7.4 was measured as 2.95. Copyright

Effects of altering the electronics of 2-methoxyestradiol on cell proliferation, on cytotoxicity in human cancer cell cultures, and on tubulin polymerization

A series of new analogues of 2-methoxyestradiol (1) were synthesized to further elucidate the relationships between structure and activity. The compounds were designed to diminish the potential for metabolic deactivation at positions 2 and 17 and were analyzed as inhibitors of tubulin polymerization and for cytotoxicity. 17α-Methyl-β-estradiol (30), 2-propynyl-17α- methylestradiol (39), 2-ethoxy-17-(1′-methylene)estra-1,3,5(10)-triene-3- ol (50) and 2-ethoxy-17α-methylestradiol (51) showed similar or greater tubulin polymerization inhibition than 2-methoxyestradiol (1) and contained moieties that are expected to inhibit deactivating metabolic processes. All of the compounds tested were cytotoxic in the panel of 55 human cancer cell cultures, and generally, the derivatives that displayed the most activity against tubulin were also the most cytotoxic.