26357-07-3

Basic information

• Product Name: 3-(benzyloxy)-2-methoxyestra-1,3,5⁽¹⁰⁾-trien-17-one
• Synonyms: 3-(benzyloxy)-2-methoxyestra-1,3,5⁽¹⁰⁾-trien-17-one
• CAS NO: 26357-07-3
• Molecular Weight: 390.522
• Mol File: 26357-07-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 3-(benzyloxy)-2-methoxyestra-1,3,5⁽¹⁰⁾-trien-17-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(benzyloxy)-2-methoxyestra-1,3,5⁽¹⁰⁾-trien-17-one(26357-07-3)
• EPA Substance Registry System: 3-(benzyloxy)-2-methoxyestra-1,3,5⁽¹⁰⁾-trien-17-one(26357-07-3)

Safety Data

• Hazardous Substances Data: 26357-07-3(Hazardous Substances Data)

Upstream product

• 26356-52-5 3-benzyloxyestra-1,3,5(10)-triene-2,17β-diol diacetate 
• 26356-51-4 2-acetyl-3-benzyloxyestra-1,3,5(10)-triene-17β-ol 17-acetate 
• 26362-44-7 2-acetyl-estra-1,3,5(10)-triene-3,17β-diol 17-acetate 
• 1474-52-8 estradiol-3,17-diacetate 
• 50-28-2 estradiol 
• 362-08-3 2-methoxyestrone 
• 26357-05-1 Acetic acid (8R,9S,13S,14S)-3-benzyloxy-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-2-yl ester 
• 1624-62-0 estrone 3-methyl ether 
• 26357-03-9 2-acetyl-3-methoxy-estra-1,3,5⁽¹⁰⁾-trien-17-one 
• 26357-02-8 2-acetyl-3-hydroxyestra-1,3,5⁽¹⁰⁾-trien-17-one 
• 901-93-9 estrone acetate 
• 217792-90-0 (8R,9S,13S,14S,17S)-2-methoxy-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene 
• 217792-89-7 (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]phenanthren-2-ol 
• 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 

Downstream Products

• 51477-81-7 2-methoxy-3-benzyloxyestra-1,3,5⁽¹⁰⁾,16-tetraene-17-enol acetate 
• 767351-43-9 N'-(3-benzyloxy-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)-N,N-dimethyl-ethane-1,2-diamine 
• 767351-39-3 (3-benzyloxy-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)-(2-morpholin-4-yl-ethyl)-amine 
• 880649-02-5 2-methoxy-3-benzyloxyestra-1,3,5(10)-triene-17β-amine 
• 1311311-76-8 2-methoxy-3-benzyloxy-17β-(2-oxopropyl)estra-1,3,5(10)-triene 
• 1311311-75-7 2-methoxy-3-benzyloxy-17β-(2-hydroxypropyl)estra-1,3,5(10)-triene 
• 1311311-74-6 2-methoxy-3-benzyloxyestra-1,3,5(10)-triene-17β-acetaldehyde 
• 1311311-73-5 2-methoxy-3-benzyloxy-17β-cyanomethylestra-1,3,5(10)-triene 
• 1311311-91-7 2-methoxy-3-O-benzyl-17β-acetylestra-1,3,5(10)-triene 
• 1311311-90-6 2-methoxy-3-O-benzyl-17β-(1-hydroxyethyl)estra-1,3,5(10)-triene 

Relevant articles and documents

Design, synthesis and antiproliferative effect of 17β-amide derivatives of 2-methoxyestradiol and their studies on pharmacokinetics

A series of 17β-amide-2-methoxyestradiol compounds were synthesized with an aim to enhance the antiproliferative effect of 2-methoxyestradiol. The antiproliferative activity of 2-methoxyestradiol analogs against human cancer cells was investigated. 2-methoxy-3-benzyloxy-17β-chloroacetamide-1,3,5(10)-triene (5e) and 2-methoxy-3-hydroxy-17β-butyramide-1,3,5(10)-triene (6c) had comparable or better antitumor activity than 2-methoxyestradiol. The elimination half-life of 6c (t1/2β = 240.93 min) is ten times longer than 2-ME and the area under the curve was seven times (AUC0-tmin = 2068.20 ± 315.74 μg mL?1 min) higher than 2-ME, respectively. Whereas 5e had similar pharmacokinetic behavior with 2-ME (t1/2β = 22.28 min) with a t1/2β of 29.5 min. 6c had higher blood concentration, longer actuation duration and better suppression rate against S180 mouse ascites tumor than 2-methoxyestradiol.

Synthesis and structure-activity relationships of 16-modified analogs of 2-methoxyestradiol

A series of 16-modified 2-methoxyestradiol analogs were synthesized and evaluated for antiproliferative activity toward HUVEC and MDA-MB-231 cells, and for susceptibility to conjugation. In addition, the estrogenicity of these analogs was accessed by meas

COMPOUND

There is provided a compound of Formula (I) wherein (I) R is a selected from (i) an alkyloxyalkyl group (ii) a nitrile group, and wherein R is capable of forming a hydrogen bond (iii) alkylaryl group, wherein the aryl group is substituted by other than a C1-10 group (iv) alkenylaryl group wherein the aryl group is substituted (v) alkyiheteroaryl group, wherein when heteroaryl group comprises only C and N in the ring, the aryl group is substituted by other than a methyl group (vi) alkenylheteroaryl group, (vii) =N-O-alkyl or =N-O-H group (viii) branched alkenyl (ix) alkyl-alcohol group (x) amide or alkylamide wherein (a) the alkyl of the alkylamide is - CH2- or -CH2CH2-, (b) the amide is di-substituted and/or (c) the amide is substituted with at least one of a I kyl heterocycle group, al ke nyl heterocycle group, alkylheteroaryl group, alkenylheteroaryl group, heteroaryl group, alkylamine group, alkyloxyalkyl group, alkylaryl group, straight or branched alkyl group, (xi) -CHO so that R, together with R3 provide the enol tautomer (a); OR R1 together with R form (xii) a pyrazole wherein (a) R is =N-0-alkyl or =N-0-H group, (b) the pyrazole is substituted with one of alkyl-OH group, alkyl ester group, alkyloxyalkyl. group, branched alkyl group, and an amide and/or (c) the 2 position is substituted with a group selected from -OH and -0-hydrocarbyl (xiii) a heteroaryl ring to provide a compound of the formula (b); (II) Ris selected from groups capable of forming a hydrogen bond, a sulphamate group, a phosphonate group, a thiophosphonate group, a sulphonate group and a sulphonamide group; and (III) Ris selected from -OH, =O, or a -C(=O)- mimetic.