11 -酮睾酮 | 564-35-2

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 11 -酮睾酮
• 中文别名: 11-酮睾酮
• 英文名称: 11-ketotestosterone
• 英文别名: 17-hydroxyandrost-4-ene-3,11-dione；17β-hydroxy-4-androstene-3,11-dione；(8S,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-2,6,7,8,9,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
• CAS: 564-35-2
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: WTPMRQZHJLJSBO-XQALERBDSA-N

物化性质

• 熔点：
  183-184 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• 沸点：
  476.8±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)
• 碰撞截面：
  173.68 Ų [M+H]+; 184.95 Ų [M+HCOO]-

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.789
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11 -酮睾酮 在 3α-hydroxysteroid dehydrogenase type 3 、 aldo-keto reductase family member 1 type D₁ 作用下， 生成 3α,17β-dihydroxy-5β-androstan-11-one
  参考文献：
  名称：

  The A-ring reduction of 11-ketotestosterone is efficiently catalysed by AKR1D1 and SRD5A2 but not SRD5A1

  摘要：

  Testosterone and its 5 alpha-reduced form, 5 alpha-dihydrotestosterone, were previously thought to represent the only active androgens in humans. However, recent studies have shown that the potent androgen, 11-ketotestosterone, derived from the adrenal androgen precursor, 110-hydroxyandrostenedione, may in fact serve as the primary androgen in healthy women. Yet, despite recent renewed interest in these steroids, their downstream metabolism has remained undetermined. We therefore set out to investigate the metabolism of 11-ketotestosterone by characterising the 5 alpha or 50-reduction commitment step. We show that inactivation of 11-ketotestosterone is predominantly driven by AKR1D1, which efficiently catalyses the 50-reduction of 11-ketotestosterone, committing it to a metabolic pathway that terminates in 11-ketoetiocholanolone. We demonstrate that 5 alpha-reduction of 11-ketotestosterone is catalysed by SRD5A2, but not SRD5A1, and terminates in 11-ketoandrosterone, but is only responsible for a minority of 11-ketotestosterone inactivation. However, as 11-ketoetiocholanolone is also generated by the metabolism of the glucocorticoid cortisone, 11-ketoandrosterone should be considered a more specific urinary marker of 11-ketotestosterone production.

  DOI：

  10.1016/j.jsbmb.2020.105724
• 作为产物：
  描述：

  氢化可的松 在 重铬酸吡啶 、 tris-buffer 、 1,4-dihydronicotinamide adenine dinucleotide 、 17β-hydroxysteroid dehydrogenase 作用下， 以 二氯甲烷 、 乙二醇 为溶剂， 反应 45.0h， 生成 11 -酮睾酮
  参考文献：
  名称：

  A simple two-step method for the conversion of [3H]cortisol to [3H]-11-ketotestosterone

  摘要：

  Despite the existence of several protocols, problems appear to persist in the small scale chemical synthesis of radiolabeled 11-ketotestosterone from cortisol. We investigated the possibilities of using the mild oxidant pyridinium dichromate for the oxidative cleavage of the dihydroxyacetone side chain of cortisol and 17 beta-hydroxysteroid dehydrogenase for the subsequent reduction of the resulting 17-keto group. Our protocol has resulted in consistently high yields of both the intermediate, adrenosterone (70-80%), and the product, 11-ketotestosterone (up to 60%). This, taken together with the convenience and relatively low cost of our method, recommends the protocol for its use for the synthesis of [H-3]-11-ketotestosterone for endocrine studies. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00052-4

文献信息

• [EN] CYP11A1 INHIBITORS<br/>[FR] INHIBITEURS DE CYP11A1
  申请人：ORION CORP

  公开号：WO2021229152A1

  公开（公告）日：2021-11-18

  The present invention relates to a compound of formula (I) or (II) wherein R1, R2, R3, R4, R5, R23, R24, R25, R26, R27, L, A and B are as defined in claim 1, or pharmaceutically acceptable salts thereof are disclosed. The compounds of formula (I) or (II) possess utility as cytochrome P450 monooxygenase 11A1 (CYP11A1) inhibitors. The compounds are useful as medicaments in the treatment of steroid receptor, particularly androgen receptor, dependent diseases and conditions, such as prostate cancer.

  本发明涉及一种具有式（I）或（II）的化合物，其中R1、R2、R3、R4、R5、R23、R24、R25、R26、R27、L、A和B如权利要求书中所定义，或其药学上可接受的盐。式（I）或（II）的化合物具有作为细胞色素P450单加氧酶11A1（CYP11A1）抑制剂的效用。这些化合物在治疗类固醇受体，特别是雄激素受体依赖性疾病和症状，如前列腺癌中作为药物是有用的。
• [EN] PYRAN DERVATIVES AS CYP11A1 (CYTOCHROME P450 MONOOXYGENASE 11A1) INHIBITORS<br/>[FR] DÉRIVÉS DE PYRANE EN TANT QU'INHIBITEURS DE CYP11A1 (CYTOCHROME P450 MONOOXYGÉNASE 11A1)
  申请人：ORION CORP

  公开号：WO2018115591A1

  公开（公告）日：2018-06-28

  Compounds of formula (I) wherein R1, R2,R3,R4,R5,R23,R24,L, A and Bare as defined in claim 1, or pharmaceutically acceptable salts thereof are disclosed. The compounds of formula (I) possess utility as cytochrome P450 monooxygenase 11A1(CYP11A1) inhibitors. The compounds are useful as medicaments in the treatment of steroidreceptor, particularly androgen receptor,dependent diseases and conditions, such asprostate cancer.

  公式(I)的化合物，其中R1、R2、R3、R4、R5、R23、R24、L、A和B如权利要求1中定义，或其药用可接受的盐被披露。公式(I)的化合物具有作为细胞色素P450单加氧酶11A1（CYP11A1）抑制剂的使用价值。这些化合物作为药物用于治疗激素受体，尤其是雄激素受体相关的疾病和状况，如前列腺癌。
• Pyrazolones as inhibitors of 11B-hydroxysteroid dehydrogenase
  申请人：Banner Lester Bruce

  公开号：US20070049632A1

  公开（公告）日：2007-03-01

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, type II diabetes mellitus and metabolic syndrome.

  本文提供了以下式(I)的化合物： 以及其药学上可接受的盐，其中取代基如规范中所披露的那样。这些化合物及含有它们的药物组合物对于治疗诸如II型糖尿病和代谢综合征等疾病是有用的。
• Aryl sulfonyl piperidines
  申请人：Gillespie Paul

  公开号：US20060199816A1

  公开（公告）日：2006-09-07

  Provided herein are compounds of the formula (1): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, type II diabetes mellitus and metabolic syndrome.

  本文提供了以下式（1）的化合物： 以及其药学上可接受的盐，其中取代基如规范中所披露的那样。这些化合物及含有它们的药物组合物对于治疗诸如II型糖尿病和代谢综合征等疾病是有用的。
• COMPOSITIONS AND METHODS FOR TREATMENT OF VIRAL DISEASES
  申请人：Johansen Lisa M.

  公开号：US20100009970A1

  公开（公告）日：2010-01-14

  The present invention features compositions, methods, and kits useful in the treatment of viral diseases. In certain embodiments, the viral disease is caused by a single stranded RNA virus, a flaviviridae virus, or a hepatic virus. In particular embodiments, the viral disease is viral hepatitis (e.g., hepatitis A, hepatitis B, hepatitis C, hepatitis D, hepatitis E) and the agent or combination of agents includes sertraline, a sertraline analog, UK-416244, or a UK-416244 analog. Also featured are screening methods for identification of novel compounds that may be used to treat a viral disease.

  本发明涉及用于治疗病毒性疾病的组合物、方法和试剂盒。在某些实施方式中，病毒性疾病是由单链RNA病毒、黄病毒科病毒或肝病毒引起的。在特定实施方式中，病毒性疾病是病毒性肝炎（例如甲型肝炎、乙型肝炎、丙型肝炎、丁型肝炎、戊型肝炎），药剂或药剂组合包括舍曲林、舍曲林类似物、UK-416244或UK-416244类似物。还包括用于鉴定可用于治疗病毒性疾病的新化合物的筛选方法。