Δ⁴-Pregnene-20β-carboxaldehyde-3-one | 66289-21-2

• 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: Δ⁴-Pregnene-20β-carboxaldehyde-3-one
• 英文别名: Dinorcholenaldehyde；3-oxo-23,24-dinor-chol-4-en-21-al；(20R)-3-oxopregn-4-ene-20-carboxaldehyde；(20R)-3-Oxopregn-4-ene-20-carbaldehyde；(2R)-2-[(8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]propanal
• CAS: 66289-21-2
• 化学式: C₂₂H₃₂O₂
• 分子量: 328.495
• InChiKey: XVPJEGGIGJLDQK-IJDPAOOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Δ⁴-Pregnene-20β-carboxaldehyde-3-one 生成 18-cyano-3,3-ethylenedioxypregn-5-ene-20-one
  参考文献：
  名称：

  Synthesis of 11β-hydroxy-18-ethynylprogesterone: an inhibitor of aldosterone biosynthesis

  摘要：

  DOI：

  10.1016/s0040-4039(00)98416-8
• 作为产物：
  描述：

  21ξ-piperidino-23,24-dinor-chola-4,20-dien-3-one; hydrochloride 在 水 作用下， 生成 Δ⁴-Pregnene-20β-carboxaldehyde-3-one
  参考文献：
  名称：

  “Enamine” Derivatives of Steroidal Carbonyl Compounds. I

  摘要：

  DOI：

  10.1021/ja01134a048

文献信息

• Steroid 5-alpha-reductase inhibitors
  申请人：SmithKline Beckman Corporation

  公开号：US04888336A1

  公开（公告）日：1989-12-19

  Invented are 4-aza-5-alpha-8(14)-17 substituted-androsten-3-ones having an 8(14), 7(8), or 16(17) double bond, optionally also having a 1(2) double bond, pharmaceutical compositions containing the compounds, and methods of using these compounds to inhibit steroid 5-alpha-reductase.

  本发明涉及发明了4-aza-5-alpha-8（14）-17取代-雄烯-3-酮，其具有8（14），7（8）或16（17）双键，也可以具有1（2）双键，以及含有这些化合物的药物组合物，以及使用这些化合物抑制类固醇5-alpha-还原酶的方法。
• Intermediates in the preparation of steriod 5-alpha-reductase inhibitors
  申请人：Smithkline Beecham Corporation

  公开号：US05110939A1

  公开（公告）日：1992-05-05

  Invented are 4-aza-5-alpha-8(14)-17 substituted-androsten-3-ones having an 8(14), 7(8), or 16(17) double bond, optionally also having a 1(2) double bond, pharmaceutical compositions containing the compounds, and methods of using these compounds to inhibit steroid 5-alpha-reductase.

  发明了4-aza-5-alpha-8（14）-17取代-雄烯-3-酮，具有8（14）、7（8）或16（17）双键，也可以具有1（2）双键，以及含有这些化合物的制药组合物和使用这些化合物抑制类固醇5α-还原酶的方法。
• Chromium‐Doped Nickel Oxide and Nickel Nitride Mediate Selective Electrocatalytic Oxidation of Sterol Intermediates Coupled with H₂ Evolution
  作者：Suiqin Li、Shibin Wang、Jiahui He、Kai Li、Yinjie Xu、Mengxin Wang、Shuying Zhao、Yuhang Wang、Xiaonian Li、Xing Zhong、Jianguo Wang

  DOI：10.1002/anie.202306553

  日期：2023.7.24

  An electrocatalytic system comprised of Cr-NiO/GF and Cr-Ni3N/GF (GF: graphite felt) was applied to anodic electrooxidation of sterol and the cathodic hydrogen evolution reaction (HER), with a high space-time yield of 48.85 kg m−3 h−1 for steroid carbonyl and 1.82 L h−1 for H2 in a two-layer stacked flow cell. This strategy could facilitate large-scale simultaneous production of H2 and value-added

  将Cr-NiO/GF和Cr-Ni 3 N/GF（GF：石墨毡）组成的电催化体系应用于甾醇的阳极电氧化和阴极析氢反应（HER），时空产率高达48.85在两层堆叠流动池中，类固醇羰基为kg m -3  h -1 ， H 2为1.82 L h -1 。该策略可以促进H 2和增值医药羰基中间体的大规模同时生产。
• Steroid-5-alpha-reductase inhibitors
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0277002A2

  公开（公告）日：1988-08-03

  4-Aza-5-alpha-8(14)-17 substituted-androsten-­3-ones having an 8(14), 7(8), or 16(17) double bond, optionally also having a 1(2) double bond, processes for their preparation, pharmaceutical compositions contaning them and their use in therapy as inhibitors of steroid 5-alpha-reductase.

  具有8(14)、7(8)或16(17)双键，可选地还具有1(2)双键的4-氮杂-5-α-8(14)-17取代雄甾烯-3-酮、其制备工艺、包含它们的药物组合物以及它们在治疗中作为类固醇5-α-还原酶抑制剂的用途。
• Synthesis and Evaluation of Pregnane Derivatives as Inhibitors of Human Testicular 17α-Hydroxylase/C_17,20-Lyase^,
  作者：Ji-song Li、Yan Li、Chong Son、Angela M. H. Brodie

  DOI：10.1021/jm960245f

  日期：1996.1.1

  The pregnene derivatives with modifications at the 17,20-side chain and D-ring were synthesized and evaluated as inhibitors of human testicular 17 alpha-hydroxylase/C-17,C-20-lyase. The results demonstrate that compounds which have 20-substituents with moderate to strong dipole properties, such as 20-oxime (3, 20), 20 beta-ol (24, 30), and 20 beta-carboxaldehyde (27), are potent inhibitors of this enzyme complex. The 20-substituents with hydrophobic property were devoid of inhibitory activity, e.g., the dimethylhydrazones 8 and 9. The 16-ene together with 20-oxime (20) showed the most potent inhibition of this enzyme complex, whereas 17(20)-ene modification as in 17(20)-ene-20-carbonitrile (14) did not increase activity in comparison to the 20 beta-carbonitrile (16). The bioisostere of 27 with 20-aza (19) also reduced the inhibitory activity. The results showed that isomeric configurations at the 20-position of some steroidal compounds are important factors which influence the potency of the inhibition significantly (e.g., 20 beta-ols 24 and 30 were 3-5-fold more potent than 20 alpha-ols 23 and 29). As expected, some compounds based on the pregn-5-en-3 beta-ol skeleton, which is similar to the natural substrate of human testicular 17 alpha-hydroxylase/C-17,C-20-lyase in A- and B-rings, showed more potent inhibition than similar compounds which are based on the pregn-4-en-3-one skeleton (e.g., 23-25 compared to 29-31). These results suggest that A- and B-rings make significant contributions to the binding of these steroidal compounds to the 17 alpha-hydroxylase and C-17,C-20-lyase. In comparison to ketoconazole, a nonsteroidal inhibitor of 17 alpha-hydroxylase and C-17,C-20-lyase which has been used in the treatment of prostatic cancer, the steroidal compounds 20, 24, and 27 demonstrate more potent inhibition for this enzyme complex. These inhibitors warrant further investigation in biological systems. The structural features of these compounds may serve as leads in the design of new inhibitors.