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Short description : Chemical compound
Equilenin Clinical data Other names 6,8-Didehydroestrone; Estra-1,3,5(10),6,8-pentaen-3-ol-17-one Routes of administration By mouth Drug class Estrogen Identifiers
(13S ,14S )-3-hydroxy-13-methyl-12,14,15,16-tetrahydro-11H -cyclopenta[a ]phenanthren-17-one
CAS Number PubChem CID DrugBank ChemSpider UNII KEGG ChEBI ChEMBL Chemical and physical data Formula C 18 H 18 O 2 Molar mass 266.340 g·mol−1 3D model (JSmol )
O=C4[C@]3(CCc1c(ccc2c1ccc(O)c2)[C@@H]3CC4)C
InChI=1S/C18H18O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2-5,10,16,19H,6-9H2,1H3/t16-,18-/m0/s1
Y Key:PDRGHUMCVRDZLQ-WMZOPIPTSA-N
Y
N Y (what is this?) (verify)
Equilenin , also known as 6,8-didehydroestrone , as well as estra-1,3,5(10),6,8-pentaen-3-ol-17-one , is a naturally occurring steroidal estrogen obtained from the urine of pregnant mares.[1] [2] It is used as one of the components in conjugated estrogens (brand name Premarin).[2] It was the first complex natural product to be fully synthesized, in work reported by 1940 by Bachmann and Wilds.[3]
Chemistry
Synthesis
Total synthesis
The synthesis developed by the Bachmann group started from Butenand's ketone[4] – the 7-methoxy structural analog of 1,2,3,4-tetrahydrophenanthren-1-one[5] – and which can be readily prepared from 1,6-Cleve's acid.[6] The approach was based on well-established transformations like the Claisen condensation , the Reformatsky reaction , the Arndt–Eistert reaction , and the Dieckmann condensation .[3] Nicolaou described this preparation as ending the era preceding the post-World War II work of Robert Burns Woodward that introduced enantioselective synthesis ;[4] in this synthesis, a mixture of stereoisomers were prepared and then resolved ,[6] and the choice of target was partly because of the existence of only two chiral carbons and hence only four stereoisomers.[5]
The overall yield of the synthesis was 2.7% based on a twenty-step process starting from Cleve's acid.[6]
See also
References
Estrogens
ER agonists
Steroidal: Alfatradiol
Certain androgens /anabolic steroids (e.g., testosterone , testosterone esters , methyltestosterone , metandienone , nandrolone esters ) (via estrogenic metabolites)
Certain progestins (e.g., norethisterone , noretynodrel , etynodiol diacetate]], tibolone )
Clomestrone
Cloxestradiol acetate
Conjugated estriol
Conjugated estrogens
Epiestriol
Epimestrol
Esterified estrogens
Estetrol †
Estradiol
Estradiol esters (e.g., estradiol acetate , estradiol benzoate , estradiol cypionate , estradiol enanthate , estradiol undecylate , [[Chemistry:Estradiol estradiol valerate, Polyestradiol phosphate |polyestradiol phosphate]], estradiol ester mixtures (Climacteron ))
Estramustine phosphate
Estriol
Estriol esters (e.g., estriol succinate , polyestriol phosphate )
Estrone
Estrone esters
Ethinylestradiol #
Hydroxyestrone diacetate
Mestranol
Methylestradiol
Moxestrol
Nilestriol
Prasterone (dehydroepiandrosterone; DHEA)
Promestriene
Quinestradol
Quinestrol
Progonadotropins
Antiestrogens
ER antagonists (incl. SERMs /SERDs )Aromatase inhibitors Antigonadotropins
Androgens /Anabolic steroid|Anabolic steroid|Anabolic steroid ]]]]s (e.g., testosterone , testosterone esters , nandrolone esters , oxandrolone , fluoxymesterone )
D2 receptor antagonists (prolactin releasers) (e.g., domperidone , metoclopramide , risperidone , haloperidol , chlorpromazine , sulpiride )
GnRH agonists (e.g., leuprorelin , goserelin )
GnRH antagonists (e.g., cetrorelix , elagolix )
Progestogens (e.g., chlormadinone acetate , cyproterone acetate , gestonorone caproate , hydroxyprogesterone caproate , [[Chemistry:Medroxyprogesterone medroxyprogesterone acetate, Chemistry :Megestrol acetate|megestrol acetate]])
Others
ER
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
3β,5α-Dihydrolevonorgestrel
3α-Hydroxytibolone
3β-Hydroxytibolone
3β-Androstanediol
4-Androstenediol
4-Androstenedione
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α-Hydroxy-DHEA
7α-Methylestradiol
7β-Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
16α-Fluoroestradiol
16α-Hydroxy-DHEA
16α-Hydroxyestrone
16α-Iodoestradiol
16α-LE2
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
17α-Estradiol (alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
17α-Epiestriol (16α-hydroxy-17α-estradiol)
17β-Dihydroequilenin
17β-Dihydroequilin
Abiraterone
Abiraterone acetate
Alestramustine
Almestrone
Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)
Atrimustine
Bolandiol
Bolandiol dipropionate
Butolame
Clomestrone
Cloxestradiol
Conjugated estriol
Conjugated estrogens
Cyclodiol
Cyclotriol
DHEA
DHEA-S
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
Epimestrol
Equilenin
Equilin
ERA-63 (ORG-37663)
Esterified estrogens
Estetrol
Estradiol
Estramustine
Estramustine phosphate
Estrapronicate
Estrazinol
Estriol
Estrofurate
Estromustine
Estrone
Etamestrol (eptamestrol)
Ethinylestradiol
Ethinylestriol
Ethylestradiol
Etynodiol
Etynodiol diacetate
Hexolame
Hippulin
Hydroxyestrone diacetate
Lynestrenol
Lynestrenol phenylpropionate
Mestranol
Methylestradiol
Moxestrol
Mytatrienediol
Nilestriol
Norethisterone
Noretynodrel
Orestrate
Pentolame
Prodiame
Prolame
Promestriene
RU-16117
Quinestradol
Quinestrol
Tibolone
Xenoestrogens: Anise -related (e.g., anethole , anol , dianethole , dianol, photoanethole )
Chalconoids (e.g., isoliquiritigenin , phloretin , phlorizin (phloridzin) , wedelolactone )
Coumestans (e.g., coumestrol , psoralidin )
Flavonoids (incl. 7,8-DHF , 8-prenylnaringenin , apigenin , baicalein , baicalin , biochanin A , calycosin , catechin , daidzein , daidzin , ECG , EGCG , [[Chemistry:Epicateepicatechin, Chemistry :Equol|equol]], formononetin , glabrene , glabridin , Genistein|genistein ]], genistin , glycitein , kaempferol, Chemistry :Liquiritigenin
Mixed (SERMs ) Antagonists
Coregulator-binding modulators: ERX-11
GPER
Original source: https://en.wikipedia.org/wiki/Equilenin. Read more