雄烯二醇17-乙酸酯 | 5937-72-4

• 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: 雄烯二醇17-乙酸酯
• 英文名称: androstenediol-17-acetate
• 英文别名: androst-5-en-3β,17β-diol 17-acetate；17β-acetoxy-androst-5-en-3β-ol；Essigsaeure-(3β-hydroxy-androsten-(5)-yl-(17β)-ester)；(10R)-3c-Hydroxy-17c-acetoxy-10r.13c-dimethyl-(8cH.9tH.14tH)-Δ⁵-tetradecahydro-1H-cyclopenta[a]phenanthren；Androstenediol 17-acetate；[(3S,8R,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
• CAS: 5937-72-4
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: BMDNPBLUVJZAEA-BPSSIEEOSA-N

物化性质

• 熔点：
  146.5-148.5°
• 比旋光度：
  D18 -62.4° (alc)
• 沸点：
  438.3±38.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

制备方法与用途

生物活性 Androstenediol 17-acetate 是一种合成代谢雄激素类固醇和雄激素酯。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  (3b,17b)-雄甾-5-烯-3,17-二醇 3,17-二乙酸酯	androstenediol-3,17-diacetate	2099-26-5	C23H34O4	374.521
  雄烯二醇	5-androstenediol	521-17-5	C19H30O2	290.446
  孕烯醇酮	Pregnenolone	145-13-1	C21H32O2	316.484
  去氢表雄酮	dehydroepiandrosterone	53-43-0	C19H28O2	288.43

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3-Oxo-17β-acetoxy-androsten-(5)	5252-16-4	C21H30O3	330.467
  醋酸睾酮	testosterone acetate	1045-69-8	C21H30O3	330.467
  ——	17beta-Acetoxyandrost-4-ene-3,6-dione	4594-27-8	C21H28O4	344.451
  睾酮	testosterone	58-22-0	C19H28O2	288.43

反应信息

• 作为反应物：
  描述：

  雄烯二醇17-乙酸酯 在 氢氧化钾 、 溴 、 溶剂黄146 作用下， 生成 睾酮
  参考文献：
  名称：

  Butenandt; Hanisch, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1935, vol. 237, p. 89,95

  摘要：

  DOI：
• 作为产物：
  描述：

  雄烯二醇 在 甲醇 、 氢氧化钾 作用下， 生成 雄烯二醇17-乙酸酯
  参考文献：
  名称：

  FR826330

  摘要：

  公开号：

文献信息

• Hydroxylated nebivolol metabolites
  申请人：O'Donnell P. John

  公开号：US20070014733A1

  公开（公告）日：2007-01-18

  Hydroxylated nebivolol metabolites increase NO release from human endothelial cell preparations in a concentration dependent fashion following acute administration. In addition, hydroxylated nebivolol metabolites, including but not limited to 4-hydroxy-6,6′difluoro-, 4-hydroxy-5-phenol-6,6′difluoro-, and 4-hydroxy-8-pheno-6,6′difluoro-, have the ability to increase the capacity for NO release in human endothelial cells following chronic administration. This invention provides hydroxylated nebivolol metabolites and compositions comprising nebivolol and/or at least one hydroxylated metabolite of nebivolol and/or at least one additional compound used to treat cardiovascular diseases or a pharmaceutically acceptable salt thereof. In addition, this invention provides methods of treating and/or preventing vascular diseases by administering at least one hydroxylated metabolite of nebivolol that is capable of releasing a therapeutically effective amount of nitric oxide to a targeted site affected by the vascular disease. Also, this invention is directed to the treatment and/or prevention of migraine headaches administering at least one hydroxylated metabolite of nebivolol. This invention may also be used in conjunction with or as a single treatment of metabolic syndrome disorders.

  羟基化奈必洛尔代谢物在急性给药后以浓度依赖性方式增加人内皮细胞制剂的一氧化氮释放。此外，羟基化奈必洛尔代谢物，包括但不限于4-羟基-6,6'-二氟代-、4-羟基-5-苯酚-6,6'-二氟代-和4-羟基-8-苯并-6,6'-二氟代-，在慢性给药后能够增加人内皮细胞的一氧化氮释放能力。本发明提供了羟基化奈必洛尔代谢物和包含奈必洛尔和/或至少一种羟基化奈必洛尔代谢物和/或至少一种用于治疗心血管疾病的附加化合物的组合物，以及可药用的盐。此外，本发明还提供了通过给药至少一种能够释放治疗有效量的一氧化氮到受血管疾病影响的靶向部位的羟基化奈必洛尔代谢物来治疗和/或预防血管疾病的方法。本发明还涉及通过给药至少一种羟基化奈必洛尔代谢物来治疗和/或预防偏头痛。本发明还可以与治疗代谢综合征障碍的其他治疗联合使用，或作为单一治疗。
• Enzymatic transesterification of steroid esters in organic solvents
  作者：Vincent C.O. Njar、Eliahu Caspi

  DOI：10.1016/s0040-4039(00)96910-7

  日期：——

  A mild procedure for the conversion of steroid esters into the corresponding alcohols via lipase-catalyzed transesterification reaction in organic solvents is described. Aspects of stereoselectivity and regioselectivity of the reaction are noted.

  描述了一种在有机溶剂中通过脂肪酶催化的酯交换反应将甾族酯转化为相应醇的温和方法。记录了反应的立体选择性和区域选择性的方面。
• TWO-FOLD CYCLOALKYLATIONS OF A BICYCLO[3.3.0]OCTANE-3,7-DIONE
  作者：Eckehard Volker Dehmlow、Hans-Jorg Breyholz、Beate Neumann、Hans-Georg Stammler

  DOI：10.1080/00304940109356607

  日期：2001.8

  5-dicarboxylate with 2-halomethylallyl halides to give cycloheptane derivatives was reported quite recently by Rodriguez et a l . (Eq. Our interest in double ring enlargements of substituted bicyclo[3.3.0]octanes to bicyclo[5.5.0]dodecanes as possible intermediates for certain polycycles,3.4 prompted us to apply this new reaction to compound l.s

  Rodriguez 等人最近报道了一种优雅的三步一锅环扩大环戊酮-2,5-二羧酸二甲酯与 2-卤代甲基烯丙基卤化物的环庚烷衍生物。（方程式：我们对取代双环 [3.3.0] 辛烷双环扩大为双环 [5.5.0] 十二烷作为某些多环的可能中间体的兴趣，3.4 促使我们将这种新反应应用于化合物 ls
• Polycyclic Ketone Monooxygenase from the Thermophilic Fungus <i>Thermothelomyces thermophila</i>: A Structurally Distinct Biocatalyst for Bulky Substrates
  作者：Maximilian J. L. J. Fürst、Simone Savino、Hanna M. Dudek、J. Rúben Gómez Castellanos、Cora Gutiérrez de Souza、Stefano Rovida、Marco W. Fraaije、Andrea Mattevi

  DOI：10.1021/jacs.6b12246

  日期：2017.1.18

  thermophila, determined its three-dimensional structure, and demonstrated its use as a promising biocatalyst. This fungal enzyme displays excellent enantioselectivity, acts on various ketones, and is particularly active on polycyclic molecules. Most notably we observed that the enzyme can perform oxidations on both the A and D ring when converting steroids. These functional properties can be linked to unique

  区域选择性和立体选择性 Baeyer-Villiger 氧化很难通过经典的化学方法实现，特别是当要转化大的官能化分子时。使用含黄素的 Baeyer-Villiger 单加氧酶 (BVMO) 进行生物催化是解决这些挑战的成熟工具，但已知的 BVMO 在稳定性或底物选择性方面存在缺陷。我们对来自嗜热真菌嗜热嗜热菌的新型 BVMO 进行了表征，确定了其三维结构，并证明了其作为一种有前途的生物催化剂的用途。这种真菌酶表现出优异的对映选择性，作用于各种酮，对多环分子特别活跃。最值得注意的是，我们观察到该酶在转化类固醇时可以对 A 环和 D 环进行氧化。
• Glucuronidated nebivolol metabolites
  申请人：O'Donnell P. John

  公开号：US20070014734A1

  公开（公告）日：2007-01-18

  This invention provides glucuronidated nebivolol metabolites and pharmaceutical compositions of glucuronidated nebivolol metabolites for treatment of cardiovascular diseases. In addition, this invention also provides compositions comprising nebivolol and/or at least one glucuronidated metabolite of nebivolol and/or at least one other active compound in a pharmaceutically acceptable carrier. This invention also provides methods of treating and/or preventing vascular diseases, by administering at least one glucuronidated metabolite of nebivolol that is capable of releasing a therapeutically effective amount of nitric oxide to a targeted site affected by the vascular disease. Also, this invention is directed to the treatment and/or prevention of migraine headaches administering at least one glucuronidated metabolite of nebivolol. This invention may also be used in conjunction with or as a single treatment of metabolic syndrome disorders.

  这项发明提供了葡萄糖醛酸化的尼布ivolol代谢物以及用于治疗心血管疾病的葡萄糖醛酸化的尼布ivolol代谢物的制药组合物。此外，该发明还提供了包含尼布ivolol和/或至少一种尼布ivolol的葡萄糖醛酸化代谢物和/或至少一种其他活性化合物的药用可接受载体的组合物。该发明还提供了通过向受影响血管疾病的靶位点投与至少一种能释放治疗有效量一氧化氮的尼布ivolol的葡萄糖醛酸化代谢物来治疗和/或预防血管疾病的方法。此外，该发明旨在通过投与至少一种尼布ivolol的葡萄糖醛酸化代谢物来治疗和/或预防偏头痛。该发明还可与代谢综合征紊乱的单一治疗或联合治疗一起使用。