(22R,23R,24S)-3β-bromo-5α,22,23-trihydroxystigmastan-6-one

• 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: (22R,23R,24S)-3β-bromo-5α,22,23-trihydroxystigmastan-6-one
• 英文别名: (22R,23R)-3β-bromo-5α,22,23-trihydroxystigmastan-6-one；(22R,23R)-3b-bromo-5a,22,23-trihydroxystigmastan-6-one；(3S,5R,8S,9S,10R,13S,14S,17R)-3-bromo-17-[(1S,2R,3R,4S)-4-ethyl-2,3-dihydroxy-1,5-dimethyl-hexyl]-5-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one；(3S,5R,8S,9S,10R,13S,14S,17R)-3-bromo-17-[(2S,3R,4R,5S)-5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl]-5-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one
• 化学式: C₂₉H₄₉BrO₄
• 分子量: 541.61
• InChiKey: YULZMZJSERMVLA-VGEPHDSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (22E)-5,6-epoxy-3β-tosyloxystigmast-22-ene 在 potassium osmate(VI) 、 potassium carbonate 高氯酸 、 甲基磺酰胺 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 pyridinium chlorochromate 、 lithium bromide 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 228.0h， 生成 (22R,23R,24S)-3β-bromo-5α,22,23-trihydroxystigmastan-6-one
  参考文献：
  名称：

  Synthesis and bioactivity evaluation of brassinosteroid analogs

  摘要：

  Four new analogs of 28-homocastasterone have been synthesized and completely characterized for the first time from stigmasterol. (22R,23R,24S)-3 beta-acetoxy-22,23-dihydroxy-5 alpha-stigmastan-6-one (17), (22R,23R,24S)-3 beta-bromo-22,23-dihydroxy-5 alpha-stigmastan-6-one (18), (22R,23R,24S)-3 beta-acetoxy-5,22,23-trihydroxy-5 alpha-stigmastan-6-one (20), and (22R,23R,24S)-3 beta-bromo-5,22,23-trihydroxy-5 alpha-stigmastan-6-one (21), were obtained through a synthetic route based on regioselective Delta(5) epoxidation. Compounds 17 and 18, bearing a 5 alpha H moiety, were prepared through a reductive opening of the 5 beta,6 beta epoxy precursor, and compounds 20 and 21, analogs with a 5 alpha OH moiety were obtained by hydrolytic opening of a mixture of 5 alpha,6 alpha and 5 beta,6 beta epoxy precursors. Known compounds 19 and 22 were also obtained following the described synthetic routes, respectively. The new compounds were tested with the traditional auxin-like bioassay for brassinosteroids with 19 and 22 as standards. All compounds were comparatively evaluated for their inhibitory effect on the replication of DNA (HSV-1) virus. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00093-3

文献信息

• Synthesis and bioactivity evaluation of brassinosteroid analogs
  作者：Javier A Ramı́rez、Osvaldo M Teme Centurión、Eduardo G Gros、Lydia R Galagovsky

  DOI：10.1016/s0039-128x(00)00093-3

  日期：2000.6

  Four new analogs of 28-homocastasterone have been synthesized and completely characterized for the first time from stigmasterol. (22R,23R,24S)-3 beta-acetoxy-22,23-dihydroxy-5 alpha-stigmastan-6-one (17), (22R,23R,24S)-3 beta-bromo-22,23-dihydroxy-5 alpha-stigmastan-6-one (18), (22R,23R,24S)-3 beta-acetoxy-5,22,23-trihydroxy-5 alpha-stigmastan-6-one (20), and (22R,23R,24S)-3 beta-bromo-5,22,23-trihydroxy-5 alpha-stigmastan-6-one (21), were obtained through a synthetic route based on regioselective Delta(5) epoxidation. Compounds 17 and 18, bearing a 5 alpha H moiety, were prepared through a reductive opening of the 5 beta,6 beta epoxy precursor, and compounds 20 and 21, analogs with a 5 alpha OH moiety were obtained by hydrolytic opening of a mixture of 5 alpha,6 alpha and 5 beta,6 beta epoxy precursors. Known compounds 19 and 22 were also obtained following the described synthetic routes, respectively. The new compounds were tested with the traditional auxin-like bioassay for brassinosteroids with 19 and 22 as standards. All compounds were comparatively evaluated for their inhibitory effect on the replication of DNA (HSV-1) virus. (C) 2000 Elsevier Science Inc. All rights reserved.