(3β,5α)-3-[(methylsulfonyl)oxy]androstan-17-one | 19646-53-8

• 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: (3β,5α)-3-[(methylsulfonyl)oxy]androstan-17-one
• 英文别名: 3β-mesyloxy-5α-androstan-17-one；epiandrosterone methanesulfonate；(3β,5α)-3-hydroxyandrostan-17-one,3-mesylate；3-mesyloxy-androstan-17-one；(3I(2),5I+/-)-3-[(Methylsulfonyl)oxy]androstan-17-one；[(3S,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] methanesulfonate
• CAS: 19646-53-8
• 化学式: C₂₀H₃₂O₄S
• 分子量: 368.538
• InChiKey: VTSXFSYSSRLCLG-WSVRAQSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3β,5α)-3-[(methylsulfonyl)oxy]androstan-17-one 在 N-甲基吗啉 、 甲醇 、 18-冠醚-6 、 potassium acetate 、 sodium hydroxide 作用下， 反应 28.0h， 生成 雄酮
  参考文献：
  名称：

  甾体化合物3位羟基构型翻转方法

  摘要：

  本发明公开了一种甾体化合物3位羟基构型翻转方法，具有以下步骤：①含有3位羟基的甾体化合物与酰氯化合物的反应；②步骤①的产物与取代试剂在相转移催化剂的存在下的SN2亲核取代反应；③步骤②的产物的水解反应。本发明的方法相比于Mitsunobu法无需使用价格较高的三苯基膦和偶氮二甲酸酯，从而大大降低了生产成本；而且也无需采用严重影响水体环境的对硝基苯甲酸衍生物，从而对环境更加友好。本发明的方法采用乙酸铯/18‑冠醚‑6体系进行3位羟基构型翻转，能够大大减少副反应的发生，从而获得较高的反应收率，最终适合工业化生产。

  公开号：

  CN108864237B
• 作为产物：
  描述：

  3-mesyloxy-17-methoxyandrostane 在 三氯乙腈 、 间氯过氧苯甲酸 作用下， 以 乙腈 为溶剂， 反应 24.5h， 以86%的产率得到(3β,5α)-3-[(methylsulfonyl)oxy]androstan-17-one
  参考文献：
  名称：

  CCl₃CN: A Crucial Promoter of mCPBA-Mediated Direct Ether Oxidation

  摘要：

  The direct oxidation of ether sp(3) C-H bonds using the new reagent system mCPBA/CCl3CN/MeCN has been developed. CCl3CN in MeCN drastically alters the reactivity of m-chloroperbenzoic acid (mCPBA), and chemoselective transformation of methyl ethers to ketones was realized under mild conditions. Radical-based mCPBA-mediated oxidation was suggested as the reaction mechanism. The present new reaction expands the utility of methyl ethers as stable synthetic precursors of carbonyl compounds and of mCPBA as a radical-based C-H oxidizing agent.

  DOI：

  10.1021/ol1018079

文献信息

• Development of Selective Steroid Inhibitors for the Glucose-6-phosphate Dehydrogenase from <i>Trypanosoma cruzi</i>
  作者：Fabrício Fredo Naciuk、Jéssica do Nascimento Faria、Amanda Gonçalves Eufrásio、Artur Torres Cordeiro、Marjorie Bruder

  DOI：10.1021/acsmedchemlett.0c00106

  日期：2020.6.11

  drug candidates. To address this issue, one strategy could be probing the susceptibility of Trypanosoma parasites toward NADP-dependent enzyme inhibitors. Recently, steroids of the androstane group have been described as highly potent but nonselective inhibitors of parasitic glucose-6-phosphate dehydrogenase (G6PDH). In order to promote selectivity, we have synthesized and evaluated 26 steroid derivatives

  恰加斯病是一种寄生虫感染，影响了拉丁美洲的数百万人，给社会经济造成了沉重负担。尽管有药物，尼富替莫和苯硝唑可供使用，但缺乏疗效和副作用的发生率促使人们鉴定出新颖，有效和负担得起的药物。为了解决这个问题，一种策略可能是研究锥虫的易感性寄生于NADP依赖性酶抑制剂。近来，雄甾烷类的类固醇已被描述为高效的但非选择性的6-葡萄糖葡萄糖磷酸脱氢酶（G6PDH）抑制剂。为了促进选择性，我们在酶测定合成并评价表雄酮的26类固醇衍生物，由此示出17种化合物显示中等至高选择性锥虫在人类G6PDH。此外，三种化合物可有效杀死感染大鼠心肌细胞的胞内克鲁氏梭菌形式。总之，这项研究提供了有关G6PDH的新SAR数据，并进一步支持了该目标以治疗南美锥虫病。
• Epiandrosterone-derived prolinamide as an efficient asymmetric catalyst for Michael addition reactions of aldehydes to nitroalkenes
  作者：Yongchao Wang、Shen Ji、Kun Wei、Jun Lin

  DOI：10.1039/c4ra03075c

  日期：——

  Epiandrosterone derivatives-organocatalyzed asymmetric Michael addition of aldehydes to nitroalkenes was investigated. Among the various catalysts, a novel type of epiandrosterone-derived L-prolineamide catalyst was synthesized and exhibited better performance in both catalytic activity and stereoselectivity, providing the products with high yields (up to 98%), excellent enantioselectivities (up to

  研究了表雄甾酮衍生物-有机催化的醛向硝基烯烃的不对称迈克尔加成反应。在各种催化剂中，合成了新型的表雄甾酮衍生的L-脯氨酸酰胺催化剂，并在催化活性和立体选择性方面均表现出更好的性能，从而提供了高收率（高达98％），优异的对映选择性（高达99％ee）的产物。 ）和非对映选择性（高达99：1 dr），催化剂负载量低（5 mol％）。
• Colonna,S. et al., Journal of the Chemical Society. Perkin transactions I, 1979, p. 2248 - 2252
  作者：Colonna,S. et al.

  DOI：——

  日期：——
• Neurosteroid Analogues. 18. Structure–Activity Studies of <i>ent</i>-Steroid Potentiators of γ-Aminobutyric Acid Type A Receptors and Comparison of Their Activities with Those of Alphaxalone and Allopregnanolone
  作者：Mingxing Qian、Kathiresan Krishnan、Eva Kudova、Ping Li、Brad D. Manion、Amanda Taylor、George Elias、Gustav Akk、Alex S. Evers、Charles F. Zorumski、Steven Mennerick、Douglas F. Covey

  DOI：10.1021/jm401577c

  日期：2014.1.9

  A model of the alignment of neurosteroids and ent-neurosteroids at the same binding site on gamma-aminobutyric acid type A (GABA(A)) receptors was evaluated for its ability to identify the structural features in ent-neurosteroids that enhance their activity as positive allosteric modulators of this receptor. Structural features that were identified included: (1) a ketone group at position C-16, (2) an axial 4 alpha-OMe group, and (3) a C-18 methyl group. Two ent-steroids were identified that were more potent than the anesthetic steroid alphaxalone in their threshold for and duration of loss of the righting reflex in mice. In tadpoles, loss of righting reflex for these two ent-steroids 0 occurs with EC50 values similar to those found for allopregnanolone. The results indicate that ent-steroids have considerable potential to be developed as anesthetic agents and as drugs to treat brain disorders that are ameliorated by positive allosteric modulators of GABA(A) receptor function.
• Seto, Hideharu; Qian, Zhao-hui; Yoshioka, Hirosuke, Chemistry Letters, 1991, p. 1185 - 1188
  作者：Seto, Hideharu、Qian, Zhao-hui、Yoshioka, Hirosuke、Uchibori, Yukitaka、Umeno, Masayuki

  DOI：——

  日期：——