9-hydroxy-4-androstene-3, 17-dione ( 4-OHA)(txuas:https://www.bloomtechz.com/synthetic-chemical/api-researching-only/9-hydroxy-4-androstene-3-17-dione-cas-560-62.html) yog ib qho steroid compound. Vim tias nws cov qauv molecular muaj ntau pawg ua haujlwm thiab cov stereoisomers, nws muaj ntau yam kev ua ub no thiab cov tshuaj pharmacological. 9-hydroxy-4-androstene-3, 17-dione (4-OHA) yog cov tshuaj steroid, nws lub npe puv yog 9-hydroxy{{6 }}androstene-3, 17-dione.
9-hydroxy-4-androstene-3, 17-dione qauv:
1. Main skeleton structure:
9-hydroxy-4-androstene-3, 17-dione belongs rau androstenoid steroids thiab muaj cov pob txha androstene. Nws lub cev pob txha tseem ceeb muaj plaub lub nplhaib, suav nrog peb lub nplhaib rau tus tswv cuab thiab ib lub nplhaib tsib tus tswv cuab. Cov plaub lub nplhaib no raug suav ua raws li A nplhaib, B nplhaib, C nplhaib thiab D nplhaib.
2. Pab pawg ua haujlwm:
Hauv cov qauv ntawm 9-hydroxy-4-androstene-3, 17-dione, muaj ntau pawg ua haujlwm tseem ceeb. Ntawm lawv, pawg hydroxyl (-OH) nyob rau ntawm cuaj carbon ntawm A nplhaib, uas yog lub hauv paus ntawm "9-hydroxy" hauv lub npe compound. Tsis tas li ntawd, muaj ob pawg keto (-C=O), uas nyob rau ntawm qhov thib peb carbon thiab kaum xya carbon ntawm lub nplhaib B, uas yog ib feem ntawm "4-androstene{{ 9}}, 17-Dion".
3. Peb-dimensional configuration:
Hais txog lub tso suab configuration, 9-hydroxy-4-androstene-3, 17-dione muaj ntau lub chaw chiral, yog li muaj ntau lub isomers tuaj yeem muaj nyob. Cov chaw chiral no nyob ntawm tsib carbon (C-5), thib rau carbon (C-6), thiab xya carbon (C-7) ntawm lub nplhaib A, thiab kaum cuaj carbon ( C-19) ntawm lub nplhaib D, feem. Qhov no txhais tau hais tias tej zaum yuav muaj 16 qhov sib txawv isomers, uas nws lub stereoconfiguration yuav muaj kev cuam tshuam tseem ceeb rau nws cov kev ua lom lom.
4. Bond ntev thiab daim ntawv cog lus lub kaum ntse ntse:
Hauv cov qauv ntawm {{0}}hydroxy-4-androstene-3, 17-dione, daim ntawv cog lus ntev thiab daim ntawv cog lus ntawm txhua lub atom tuaj yeem txiav txim siab los ntawm kev sim tshuaj thiab kev suav txoj kev. Ntawm lawv, carbon-carbon (CC) thiab carbon-hydrogen (CH) daim ntawv cog lus feem ntau muaj qhov nruab nrab daim ntawv cog lus ntev li ntawm 1.54 Å thiab txog 1.09 Å. Tsis tas li ntawd, qhov ntev ntawm carbon-oxygen (CO) daim ntawv cog lus feem ntau yog 1.43 Å, thiab qhov ntev ntawm cov pa oxygen-hydrogen bonds (OH) ntawm pawg hydroxyl feem ntau yog li 0.96 Å. Cov pa roj carbon-keto (C=O) daim ntawv cog lus muaj daim ntawv cog lus ntev li ntawm 1.22 Å.
5. Resonant qauv:
Vim tias muaj ntau daim ntawv cog lus ob leeg thiab cov pab pawg ua haujlwm, 9-hydroxy-4-androstene-3, 17-dione muaj cov qauv ntawm cov resonance. Cov qauv resonance tuaj yeem piav qhia nws cov khoom thiab cov lus teb tus cwj pwm, thiab nthuav qhia ntxiv txog nws txoj haujlwm hauv vivo.
9-hydroxy-4-androstene-3 17- dione khoom:
1. Cov tshuaj tiv thaiv oxidation:
9-hydroxy-4-androstene-3, 17-dione (9-hydroxy-4-androstene-3,17-dione) yog ib qho active steroid compound, uas tuaj yeem ua rau muaj ntau yam kev cuam tshuam oxidation. Nws tuaj yeem oxidized los ntawm oxidizing tus neeg sawv cev rau nws cov derivatives, xws li ketone lub cev 4-androstene-3, 17-dione lossis methylated khoom. Cov tshuaj tiv thaiv no tuaj yeem ua tau los ntawm kev siv cov tshuaj oxidizing (xws li chromic acid, hydrogen peroxide) lossis lwm yam catalysts.
9-hydroxy-4-androstene-3, 17-dione (9-hydroxy-4-androstene-3,17-dione) yog ib qho active steroid compound, uas tuaj yeem ua rau muaj ntau yam kev cuam tshuam oxidation.
1.1. Ketone lub cev tsim cov tshuaj tiv thaiv:
9-Hydroxy-4-androstene-3, 17-dione tuaj yeem oxidized rau lub cev ketone, xws li 4-androstene-3, {{6 }}dione (4-androstene-3, 17-dione).
Tshuaj formula:
C19H26O3 → C19H26O2 plus H2O
1.2. Hydroxyoxidation cov tshuaj tiv thaiv:
9-Hydroxy-4-androstene-3, 17-dione kuj tseem tuaj yeem oxidized los ntawm oxidizing cov neeg ua hauj lwm rau cov derivatives nrog ntau dua oxidation xeev, xws li 9,11 -epoxy{{ 6}}hydroxy-4-androstene-3,20 - Dione (9,11 -epoxy-17 -hydroxy-4-androstene-3,{ {15}}dione).
Tshuaj formula:
C19H26O3 plus oxidizing agent → 9,11 -epoxy-17 -hydroxy-4-androstene-3,20-dione plus H2O
1.3. Hydroxymethylation cov tshuaj tiv thaiv:
Raws li qee qhov tshwj xeeb, 9-hydroxy-4-androstene-3, 17-dione tuaj yeem hydroxymethylated los ntawm oxidation cov tshuaj tiv thaiv los tsim cov hydroxymethyl compound, xws li 9-hydroxy -11 -methyl- 4-androstene-3, 17-dione (9-hydroxy-11 -methyl-4-androstene-3,{ {13}}dione).
Tshuaj formula:
C19H26O3 ntxiv rau oxidizing tus neeg sawv cev ntxiv rau methyl pub dawb → 9-hydroxy-11 -methyl-4-androstene -3,17-dione ntxiv H2O
2. Txo cov tshuaj tiv thaiv:
9-hydroxy-4-androstene-3, 17-dione tuaj yeem hloov mus rau hauv nws cov khoom siv metabolic, xws li testosterone lossis dihydrotestosterone, los ntawm kev txo cov tshuaj tiv thaiv. Cov tshuaj tiv thaiv no tuaj yeem ua tiav siv cov tshuaj txo qis (xws li hydrogen, hlau catalysts) lossis reductases.
2.1. Ketone txo qis:
9-Hydroxy-4-androstene-3, 17-dione tuaj yeem txo qis rau testosterone lossis dihydrotestosterone los ntawm kev txo ketone.
Tshuaj formula:
C19H26O3 + NADH + H plus → C19H28O2 + NAD + H2O
2.2. Hydroxyl txo:
Cov pab pawg hydroxyl ntawm 9-hydroxy-4-androstene-3, 17-dione kuj tuaj yeem raug txo rau cov tshuaj methyl los ntawm kev txo cov tshuaj tiv thaiv, xws li 9 -methyl{{5 }}androstene-3,17-dione (9 -methyl -4-androstene-3,17-dione).
Tshuaj formula:
C19H26O3 plus NADPH plus H plus → 9 -methyl-4-androstene-3, 17-dione plus NADP plus plus H2O
2.3. Kev txo qis ntawm cycloalcohols:
Lub cyclic cawv ntawm 9-hydroxy-4-androstene-3, 17-dione kuj tuaj yeem raug txo rau cov khoom lag luam cyclic ether.
Tshuaj formula:
C19H26O3 ntxiv rau NADH ntxiv rau H ntxiv → cyclic ether khoom ntxiv rau NAD ntxiv ntxiv ntxiv H2O
3. Cov tshuaj tiv thaiv lub cev qhuav dej:
9-hydroxy-4-androstene-3, 17-dione raug lub cev qhuav dej nyob rau hauv cov xwm txheej tsim nyog los tsim cov khoom nrog ob daim ntawv cog lus thiab cov khoom sib txuas nrog cov qauv sib txawv. Piv txwv li 4-androstene-3,17-dione (4-androstene-3,17-dione).
3.1. -hydroxyl lub cev qhuav dej:
Raws li cov xwm txheej tsim nyog, 9-hydroxy-4-androstene-3, 17-dione tuaj yeem raug cov tshuaj tiv thaiv -hydroxy dehydration los tsim cov tshuaj estrogenic sib xws, xws li estrone (estrone) lossis { {5}}estradiol (estradiol).
Tshuaj formula:
C19H26O3 → estrogenic compound plus H2O
3.2. Hydroxydehydration:
Lwm cov tshuaj tiv thaiv lub cev qhuav dej yog lub cev qhuav dej ntawm pawg hydroxyl ntawm 9-hydroxy-4-androstene-3, 17-dione los tsim cov khoom sib txuam alkene.
Tshuaj formula:
C19H26O3 → olefin compound ntxiv H2O
4. Cov tshuaj tiv thaiv Esterification:
Cov pab pawg hydroxyl ntawm 9-hydroxy-4-androstene-3, 17-dione tuaj yeem ua rau cov kua qaub los tsim cov ester compounds. Cov tshuaj tiv thaiv no feem ntau xav tau cov kua qaub catalyst thiab yog nrog los ntawm kev tsim cov dej.
Piv txwv ntawm cov tshuaj tiv thaiv esterification:
C19H26O3 ntxiv rau acid / anhydride → ester
Ntawm lawv, cov kua qaub / anhydride tuaj yeem yog qee yam acidic compound lossis anhydride, feem ntau siv cov kua qaub xws li benzoic acid, acetic acid thiab lwm yam. Cov tshuaj tiv thaiv esterification feem ntau xav tau cov tshuaj tiv thaiv tsim nyog thiab ua tiav hauv cov kuab tshuaj tsim nyog.
5. Ketone txo cov tshuaj tiv thaiv:
Cov ketone pawg ntawm 9-hydroxy-4-androstene-3, 17-dione tuaj yeem txo los ntawm dehydrogenase los tsim testosterone lossis dihydrotestosterone. Cov tshuaj tiv thaiv no tshwm sim dav hauv cov kab mob muaj sia.
5.1. Txo kom tsim cov testosterone (testosterone):
Raws li cov xwm txheej tsim nyog, 9-hydroxy-4-androstene-3, 17-dione tuaj yeem txo qis rau testosterone, piv txwv li 17 -hydroxy-4-androstene{{6 }}ib.
Tshuaj formula:
C19H26O3 + NADH + H plus → C19H28O2 + NAD + H2O
5.2. Txo kom tsim dihydrotestosterone (dihydrotestosterone):
Tsis tas li ntawd, 9-hydroxy-4-androstene-3, 17-dione kuj tuaj yeem raug txo kom dihydrotestosterone, 5 -dihydrotestosterone lossis 17 -hydroxy{{6 }}androstene-3-ib.
Tshuaj formula:
C19H26O3 plus NADPH plus H plus → Dihydrotestosterone plus NADP plus plus H2O