(5α,17β)-Androst-2-eno<3,2-b>furan-17-ol | 135643-79-7

• 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: (5α,17β)-Androst-2-eno<3,2-b>furan-17-ol
• 英文别名: 5α,17β-androst-2-eno<3,2-b>furan-17-ol；(5α,17β)-Androst-2-eno[3,2-b]furan-17-ol；(1S,2S,10S,13R,14S,17S,18S)-2,18-dimethyl-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-ol
• CAS: 135643-79-7
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: UUIOUWUAYNUKCZ-DGWDJNBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5α,17β)-Androst-2-eno<3,2-b>furan-17-ol 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 palladium dihydroxide 、 strontium(II) carbonate 、 氢气 、 氯化二乙基铝 、 potassium carbonate 、 二甲基亚砜 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， -78.0~25.0 ℃ 、344.73 kPa 条件下， 反应 69.5h， 生成 1-(5alpha,17 alpha-17-Hydroxypregn-2-eno[3,2-b]-furan-5'-yl)ethanone
  参考文献：
  名称：

  Androgen Receptor Affinity of 5'-Acyl Furanosteroids

  摘要：

  Syntheses of 5'-acyl furanosteroids are described from the corresponding unsubstituted [3,2-b]furanosteroids using acid anhydrides and acid chlorides in the presence or absence of Lewis acids. New methods have been developed to prepare 5'-acetyl derivatives: reduction of a 5'-trichloroacetyl intermediate either by sodium formaldehyde sulfoxylate or with 10% Pd/C. Most of these 5'-acyl derivatives bind to the rat ventral prostate androgen receptor. However the antiandrogenic activity was diminished when compared with 4, 5'-methylsulfonyl furanosteroid. Biological studies revealed that 5'-acyl furanosteroids were either androgens or modest antiandrogens. The electrostatic potential maps of the substructures of 3, 4, and 5'-acetyl syn- and anti-furanosteroids showed striking differences which may explain, to some extent, the lack of significant antiandrogenic activity of 5'-acyl furanosteroids.

  DOI：

  10.1021/jm00050a019
• 作为产物：
  描述：

  (1S,3aS,3bR,5aS,10aS,10bS,12aS)-10a,12a-Dimethyl-1-(tetrahydro-pyran-2-yloxy)-2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-tetradecahydro-1H-7-oxa-dicyclopenta[a,h]phenanthren-9-one 在 9-borabicyclo[3.3.1]nonane dimer 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 (5α,17β)-Androst-2-eno<3,2-b>furan-17-ol
  参考文献：
  名称：

  Synthesis and androgen receptor affisity of steroidal methylsulfonylforans and a menthylsulfonylthiophene

  摘要：

  Syntheses of the unsubstituted steroidal [3,2-b]furan (3a), thiophene (3b) and [2,3-b]furan (24) are described. Lithiation of the THP ethers 18a and 18b followed by the reaction with methyl disulfide and deprotection gave the 5'-methylsulfide derivatives 19a and 19b. Oxidation of the sulfides and ethynylation provided the compounds 2a and 2b. Swern oxidation of the [2,3-b]furan 24 with DMSO/TFAA/diisopropylethylamine resulted in oxidation to the 17-ketone and introduction of a 5'-methylthio group to give 25. Ethynylation at C-17 followed by oxidation of the sulfide group provided the product 27. 5'-Methylsulfonyl[3,2-b]furanosteroid 2a bound to the rat ventral prostate androgen receptor. However, the corresponding thiophene 2b and the [2,3-b]furan 27 lacked affinity for the receptor.

  DOI：

  10.1016/s0040-4020(01)87122-2

文献信息

• KUMAR, VIRENDRA;DAUM, SOL J.;BELL, MALCOLM R.;ALEXANDER, MICHAEL A.;CHRIS+, TETRAHEDRON, 47,(1991) N8, C. 5099-5110
  作者：KUMAR, VIRENDRA、DAUM, SOL J.、BELL, MALCOLM R.、ALEXANDER, MICHAEL A.、CHRIS+

  DOI：——

  日期：——