dihydroandrosterone | 62356-64-3

• 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
• 英文名称: dihydroandrosterone
• 英文别名: (3S,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 62356-64-3
• 化学式: C₁₉H₃₂O₂
• 分子量: 292.462
• InChiKey: CBMYJHIOYJEBSB-NMNWSMPISA-N

物化性质

• 沸点：
  415.0±18.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dihydroandrosterone 在 氧气 、 Langlois reagent 作用下， 以 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以79%的产率得到5a-雄甾烷二酮
  参考文献：
  名称：

  三氟甲烷亚磺酸钠介导的酒精的有氧氧化光催化策略。

  摘要：

  首次开发了三氟甲烷亚磺酸钠介导的酒精好氧氧化的光催化策略，仲醇和伯醇的光氧化还原好氧氧化分别以高至优异的产率提供了相应的酮和羧酸。

  DOI：

  10.1039/d0cc05799a
• 作为产物：
  描述：

  表雄酮 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 12.0h， 以78.5%的产率得到dihydroandrosterone
  参考文献：
  名称：

  Synthesis and characterisation of steroidal inhibitors of α-amylase, α-glucosidase and oxidative species

  摘要：

  BACKGROUND: Management of cellular metabolism and blood glucose levels are significant in the treatment of diabetes mellitus and oxidative diseases. Consequently, steroid and peptide hormone-based drugs such as methylprednisolone and insulin have been the most effective and safe methods of treatment.OBJECTIVE: Our study investigated the digestive enzymes and oxidative species inhibitory potentials of seven derived biologically important steroids.METHODS: Syntheses of the steroidal inhibitors (SIs) were accomplished by functional group transformations. Characterisation of SIs was achieved by spectroscopic techniques; followed by in-vitro enzyme and oxidative suppression studies.RESULTS: NMR data revealed the presence of a steroid backbone, azomethine, carbonyl, and oxymethine peaks while the vibrational bands were further confirmed by the FTIR. The enzyme suppression activities of the SIs were influenced by the presence of histidine residue and free proton groups. However, the antioxidant activities were solely dependent on the free proton groups on the steroid backbone or the number of the histidine side chain. SIs [3, 4, and 6] exhibited a potent inhibitory effect on the enzyme activities compared to SIs [1, 2, 5, and 7], while a potent antioxidant activity was reported by SI [5].CONCLUSIONS: Generally, SIs with hydroxyl and alpha-amino acid functionalities have a strong affinity for the enzyme active site than the substrate; hence, the hydrolysis of the alpha-1,4-glycosidic bonds of saccharide was hindered. In vivo administration of SIs [3, 4, and 6] should take into cognizance the suppression effect at doses <= 939.49 mu g/mL as well as the potential to induce abnormal bacterial fermentation of undigested carbohydrates in the colon at high concentration.

  DOI：

  10.3233/mnm-190333

文献信息

• A Convenient Method for the Preparation of 16,16-Bis[hydroxymethyl]-17-hydroxy-steroids and 16,16-Bis[hydroxymethyl]-17-oxo-steroids
  作者：Gyula Schneider、János Wölfling、László Hackler、Eszter Meskó、György Dombi

  DOI：10.1055/s-1985-31152

  日期：——
• BONE ANABOLIC COMPOUNDS AND METHODS OF USE
  申请人：Anabonix, Inc.

  公开号：EP1404344A2

  公开（公告）日：2004-04-07
• [EN] BONE ANABOLIC COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSES ANABOLISANTS OSSEUX ET LEURS PROCEDES D'UTILISATION
  申请人：ANABONIX INC

  公开号：WO2003002058A2

  公开（公告）日：2003-01-09

  A variety of bone anabolic compounds are useful for maintaining and/or increasing bone mass, density, and/or strength in mammals. Preferred compounds enhance bone anabolic activity while minimizing or eliminating undesirable feminizing or masculinizing effects.
• Synthesis and characterisation of steroidal inhibitors of α-amylase, α-glucosidase and oxidative species
  作者：Bamidele J. Okoli、Mthunzi Fanyana、James D. Habila、Ayo G. Rachael、Iloegbulam G. Ndukwe、Olugbemi T. Olaniyan、Johannes S. Modise

  DOI：10.3233/mnm-190333

  日期：2019.12.3

  BACKGROUND: Management of cellular metabolism and blood glucose levels are significant in the treatment of diabetes mellitus and oxidative diseases. Consequently, steroid and peptide hormone-based drugs such as methylprednisolone and insulin have been the most effective and safe methods of treatment.OBJECTIVE: Our study investigated the digestive enzymes and oxidative species inhibitory potentials of seven derived biologically important steroids.METHODS: Syntheses of the steroidal inhibitors (SIs) were accomplished by functional group transformations. Characterisation of SIs was achieved by spectroscopic techniques; followed by in-vitro enzyme and oxidative suppression studies.RESULTS: NMR data revealed the presence of a steroid backbone, azomethine, carbonyl, and oxymethine peaks while the vibrational bands were further confirmed by the FTIR. The enzyme suppression activities of the SIs were influenced by the presence of histidine residue and free proton groups. However, the antioxidant activities were solely dependent on the free proton groups on the steroid backbone or the number of the histidine side chain. SIs [3, 4, and 6] exhibited a potent inhibitory effect on the enzyme activities compared to SIs [1, 2, 5, and 7], while a potent antioxidant activity was reported by SI [5].CONCLUSIONS: Generally, SIs with hydroxyl and alpha-amino acid functionalities have a strong affinity for the enzyme active site than the substrate; hence, the hydrolysis of the alpha-1,4-glycosidic bonds of saccharide was hindered. In vivo administration of SIs [3, 4, and 6] should take into cognizance the suppression effect at doses <= 939.49 mu g/mL as well as the potential to induce abnormal bacterial fermentation of undigested carbohydrates in the colon at high concentration.
• A sodium trifluoromethanesulfinate-mediated photocatalytic strategy for aerobic oxidation of alcohols
  作者：Xianjin Zhu、Can Liu、Yong Liu、Haijun Yang、Hua Fu

  DOI：10.1039/d0cc05799a

  日期：——

  A sodium trifluoromethanesulfinate-mediated photocatalytic strategy for the aerobic oxidation of alcohols has been developed for the first time, and the photoredox aerobic oxidation of secondary and primary alcohols provided the corresponding ketones and carboxylic acids, respectively, in high to excellent yields.

  首次开发了三氟甲烷亚磺酸钠介导的酒精好氧氧化的光催化策略，仲醇和伯醇的光氧化还原好氧氧化分别以高至优异的产率提供了相应的酮和羧酸。