1,4-雄烯二酮(androsta-1,4-diene-3,17-dione,简称雄二烯二酮、ADD)和雄甾-4-烯-3,17-二酮(androst-4-ene-3,17-dione,简称雄烯二酮、AD或4-AD)均为重要的甾类药物中间体。雄烯二酮(4-AD)可作为雄性激素、促蛋白合成激素等激素类物质的前体,并用于合成螺甾内酯、氢化可的松、氧化泼尼松、地塞米松等药物;而雄二烯二酮(ADD)则可用于雌性激素和口服避孕药等药物的合成。
抗炎机理3-甾酮-1,2-脱氢酶(KsdD)催化雄烯二酮(4-AD)的C1,2位脱氢反应,生成1,4-雄烯二酮(ADD)。在甾体类化合物中导入双键后,如在抗炎甾体激素药物母核的C1,2位导入双键,可显著提高其抗炎作用。例如,在醋酸可的松C1,2位上导入双键形成的醋酸脱氢可的松,其抗炎作用提高了3-4倍,并减少了由钠滞留带来的副作用。许多临床上常用的甾体化合物,特别是大多数具有抗炎能力的肾上腺皮质激素(如氢化泼尼松、地塞米松、帕拉米松、倍他米松、氟可龙、氟轻松、曲安西龙和甲基强的松龙等),其生产均涉及微生物C1,2位的脱氢反应。
化学性质主要用于甾体激素类药物的中间体生产。
生产方法中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
—— | 3-thioxo-androst-1,4-dien-17-on | 57334-04-0 | C19H24OS | 300.465 |
雄烯二酮 | Androstenedione | 63-05-8 | C19H26O2 | 286.414 |
黄体酮 | Progesterone | 57-83-0 | C21H30O2 | 314.468 |
—— | progesterone | 57-83-0 | C21H30O2 | 314.468 |
宝丹酮 | 1-dehydrotestosterone | 846-48-0 | C19H26O2 | 286.414 |
1-雄烯二酮 | 5α-androst-1-ene-3,17-dione | 571-40-4 | C19H26O2 | 286.414 |
去氢表雄酮 | dehydroepiandrosterone | 53-43-0 | C19H28O2 | 288.43 |
睾酮 | testosterone | 58-22-0 | C19H28O2 | 288.43 |
1-羟基去氢表雄酮 | 1α,3β-dihydroxy-androst-5-en-17-one | 20998-18-9 | C19H28O3 | 304.43 |
孕烯醇酮醋酸酯 | Pregnenolone acetate | 1778-02-5 | C23H34O3 | 358.521 |
醋酸睾酮 | testosterone acetate | 1045-69-8 | C21H30O3 | 330.467 |
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
—— | 6α-methylandrosta-1,4-diene-3,17-dione | —— | C20H26O2 | 298.425 |
阿他美坦 | atamestane | 96301-34-7 | C20H26O2 | 298.425 |
—— | 6α-(2-Oxoethyl)androsta-1,4-dien-3,17-dion | 911856-14-9 | C21H26O3 | 326.436 |
6beta-(羟基甲基)雄甾-1,4-二烯-3,17-二酮 | 6β-hydroxymethylandrosta-1,4-diene-3,17-dione | 121021-51-0 | C20H26O3 | 314.425 |
依西美坦 | exemestane | 107868-30-4 | C20H24O2 | 296.409 |
(8R.9S.10R.13S.14S)-10.13-二甲基-7.8.9.11.12.13.15.16-八氢-10H-环戊并[a]菲-3.6.17(14H)-三酮 | androsta-1,4-dien-3,6,17-trione | 72648-46-5 | C19H22O3 | 298.382 |
—— | (8R,9S,10R,13S,14S)-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[α]phenanthrene-3,17(4H)-dione | 55835-19-3 | C19H24O2 | 284.398 |
—— | 6α-(2-Nitroethyl)androsta-1,4-dien-3,17-dion | 911856-13-8 | C21H27NO4 | 357.45 |
雄甾-1,4,6-三烯-3,17-二酮 | 1,4,6-androstatriene-3,17-dione | 633-35-2 | C19H22O2 | 282.382 |
—— | (6S,8R,9S,10R,13S,14S)-6-(methoxymethyl)-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[a]phenanthrene-3,17(6H)-dione | —— | C21H28O3 | 328.452 |
—— | 3-thioxo-androst-1,4-dien-17-on | 57334-04-0 | C19H24OS | 300.465 |
雄烯二酮 | Androstenedione | 63-05-8 | C19H26O2 | 286.414 |
1,4-雄二烯-11-beta-醇-3,17-二酮 | (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclopenta[a]phenanthrene-3,17-dione | 898-84-0 | C19H24O3 | 300.398 |
11alpha-羟基雄甾-1,4-二烯-3,17-二酮 | 11α-hydroxy-androsta-1,4-diene-3,17-dione | 7801-18-5 | C19H24O3 | 300.398 |
—— | (+)-1α-hexyl-4-androstene-3,17-dione | 1430412-87-5 | C25H38O2 | 370.576 |
—— | (+)-1β-hexyl-4-androstene-3,17-dione | 1430412-90-0 | C25H38O2 | 370.576 |
—— | 1α-methyl-androst-4-ene-3,17-dione | 4136-62-3 | C20H28O2 | 300.441 |
—— | 6-Methylen-4-androsten-3,17-dion | 19457-55-7 | C20H26O2 | 298.425 |
—— | (+)-1α-(5-bromopentyl)-4-androstene-3,17-dione | 1431943-34-8 | C24H35BrO2 | 435.445 |
—— | (8R,9S,10R,13S,14S)-6-bromo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[α]phenanthrene-3,17(6H)-dione | 94534-87-9 | C19H23BrO2 | 363.294 |
—— | 6β-bromo-androsta-1,4-diene-3,17-dione | 27759-21-3 | C19H23BrO2 | 363.294 |
—— | 4-chloroandrosta-1,4-diene-3,17-dione | 120754-97-4 | C19H23ClO2 | 318.843 |
—— | 6α-hydroxyandrosta-1,4-diene-3,17-dione | 21661-22-3 | C19H24O3 | 300.398 |
—— | Diethyl-2-(3,17-dioxoandrosta-1,4-dien-6β-ylmethyl)-malonat | —— | C27H36O6 | 456.579 |
—— | Ethyl(E)-3-oxopregna-1.4.17(20)-trien-21-oat | —— | C23H30O3 | 354.489 |
雄甾-4-烯-3β,6β,17β-三醇 | androst-4-ene-3,6,17-trione | 2243-06-3 | C19H24O3 | 300.398 |
宝丹酮 | 1-dehydrotestosterone | 846-48-0 | C19H26O2 | 286.414 |
—— | 17β-hydroxy-1,4-androstadien-3-one. | 27833-18-7 | C19H26O2 | 286.414 |
—— | (8S,9S,10R,13S,14S)-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-3-one | 71677-46-8 | C21H26O3 | 326.436 |
17-羟基-1,4-二烯-3,20-二酮 | 17α-hydroxypregna-1,4-diene-3,20-dione | 2477-61-4 | C21H28O3 | 328.452 |
(8S,9R,10S,13S,14S)-9-羟基-10,13-二甲基-6,7,8,11,12,14,15,16-八氢环戊烯并[a]菲-3,17-二酮 | 9α-hydroxyandrost-1,4-diene-3,17-dione | 82182-55-6 | C19H24O3 | 300.398 |
美雄酮 | metandienone | 72-63-9 | C20H28O2 | 300.441 |
—— | 16-(4'-chlorobenzal)androsta-1,4-diene-3,17-dione | 150634-84-7 | C26H27ClO2 | 406.952 |
—— | 16-(4'-bromobenzal)androsta-1,4-diene-3,17-dione | 150634-85-8 | C26H27BrO2 | 451.403 |
1-雄烯二酮 | 5α-androst-1-ene-3,17-dione | 571-40-4 | C19H26O2 | 286.414 |
—— | 5β-Androst-1-ene-3,17-dione | 571-39-1 | C19H26O2 | 286.414 |
3,4,5-三氯-1,2-苯二胺 | 11α,17β-dihydroxyandrosta-1,4-dien-3-one | 30915-20-9 | C19H26O3 | 302.414 |
—— | (6R,8R,9S,10R,13S,14S)-6-ethoxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[α]phenanthrene-3,17(6H)-dione | —— | C21H28O3 | 328.452 |
—— | 5β-methylandrost-1-ene-3,17-dione | 51503-64-1 | C20H28O2 | 300.441 |
—— | 4-hydroxy-1,4,6-androstatriene-3,17-dione | 95192-09-9 | C19H22O3 | 298.382 |
—— | 16-(4'-methoxybenzal)androsta-1,4-diene-3,17-dione | 150634-79-0 | C27H30O3 | 402.533 |
—— | 17α-ethynyl-17β-hydroxy-1,4-androstadien-3-one | 7162-55-2 | C21H26O2 | 310.436 |
—— | (+)-1α-(4-(chloromethyl)phenethyl)-4-androstene-3,17-dione | 1430413-10-7 | C28H35ClO2 | 439.038 |
(7R,8R,9S,10R,13S,14S)-7-(4-氨基苯基)硫基-10,13-二甲基-7,8,9,11,12,14,15,16-八氢-6H-环戊二烯并[a]菲-3,17-二酮 | 7α-(4'-amino)phenylthio-1,4-androstadiene-3,17-dione | 110325-37-6 | C25H29NO2S | 407.577 |
—— | (6R,8R,9S,10R,13S,14S)-10,13-dimethyl-3,17-dioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[α]phenanthren-6-yl propionate | 1338324-52-9 | C22H28O4 | 356.462 |
—— | [(6S,8R,9S,10R,13S,14S)-10,13-dimethyl-3,17-dioxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-6-yl] propanoate | 1380397-52-3 | C22H28O4 | 356.462 |
睾内酯 | testolactone | 968-93-4 | C19H24O3 | 300.398 |
睾酮 | testosterone | 58-22-0 | C19H28O2 | 288.43 |
表睾酮 | epitestosterone | 481-30-1 | C19H28O2 | 288.43 |
9α-羟基-4-雄甾烯-3,17-二酮 | 9-alpha-hydroxyandrost-4-ene-3,17-dione | 560-62-3 | C19H26O3 | 302.414 |
—— | [1-[(8S,9S,10R,13S,14S)-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ylidene]-2-oxoethyl] 2-methylpropanoate | 131467-41-9 | C25H32O4 | 396.527 |
—— | 6α-methoxyandrost-4-ene-3,17-dione | 13163-89-8 | C20H28O3 | 316.441 |
—— | 3-Ethoxy-androsta-3,5-dien-17-on | 972-46-3 | C21H30O2 | 314.468 |
—— | (8R,9S,10R,13S,14S)-4-diazo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[a]-phenanthrene-3,17(4H)-dione | 1150096-90-4 | C19H22N2O2 | 310.396 |
—— | (6R,8R,9S,10R,13S,14S)-6-ethoxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthrene-3,17(2H,6H)-dione | —— | C21H30O3 | 330.467 |
—— | (6S,8R,9S,10R,13S,14S)-6-ethoxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione | 325966-32-3 | C21H30O3 | 330.467 |
1-羟基去氢表雄酮 | 1α,3β-dihydroxy-androst-5-en-17-one | 20998-18-9 | C19H28O3 | 304.43 |
—— | 17-ethylendioxyandrosta-1,4-dien-3-one | —— | C21H28O3 | 328.452 |
—— | Spiro |
—— | C25H28OS2 | 408.629 |
—— | (20S)-17-Hydroxy-20-methoxy-3-oxo-17α-pregna-1,4-dien-21-saeure-methylester | —— | C23H32O5 | 388.504 |
—— | (8R,9S,10R,13S,14S)-3-hydroxy-4-methoxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthren-17(2H)-one | 1338324-47-2 | C20H28O3 | 316.441 |