(22E)-3β-bromo-5α-hydroxystigmast-22-en-6-one | 188127-57-3

• 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: (22E)-3β-bromo-5α-hydroxystigmast-22-en-6-one
• 英文别名: (3S,5R,8S,9S,10R,13R,14S,17R)-3-bromo-17-[(E,1R,4S)-4-ethyl-1,5-dimethyl-hex-2-enyl]-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,13R,14S,17R)-3-bromo-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-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
• CAS: 188127-57-3
• 化学式: C₂₉H₄₇BrO₂
• 分子量: 507.595
• InChiKey: XIGAJSQDXDXKDR-QKHDKLJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (22E)-3β-bromo-5α-hydroxystigmast-22-en-6-one 在 potassium osmate(VI) 吡啶 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 216.0h， 以89%的产率得到(3β,5α,22S,23S)-3-溴-5,22,23-三羟基豆甾烷-6-酮
  参考文献：
  名称：

  In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues

  摘要：

  Brassinosteroids area novel group of steroids that appear to be ubiquitous in p I ants and are essential for normal plant growth and development. It has been previously reported that brassinosteroid analogues exert an antiviral activity against herpes simplex virus type 1 (HSV-1) and arenaviruses. In the present study, we report the chemical synthesis of compounds (22S,23S)-3beta-bromo-5alpha,22,23-trihydroxystigmastan-6-one (2), (22S,23S)-5alpha-fluoro-3beta-22,23-trihydroxystigmastan-6-one (3), (22S,23S)-3beta,5alpha,22,23-tetrahydroxy-stigmastan-6-one (4) as well as their antiherpetic activity both in a human conjunctive cell line (IOBA-NHC) and in the murine herpetic stromal keratitis (HSK) experimental model. All compounds prevented HSV-1 multiplication in NHC cells in a dose dependent manner when added after infection with no cytotoxicity. Administration Of Compounds 2, 3, and 4 to the eyes of mice at 1, 2, and 3 days post-infection delayed and reduced the incidence of HSK, consisting mainly of inflammation, vascularization, and necrosis, compared to untreated, infected mice. However, viral titers of eye washes showed no differences among samples from treated and untreated mice. Since the decrease in the percentage of mice with ocular lesions occurred 5 days after treatment had ended, we suggest that brassinosteroids 2, 3, and 4 did not exert a direct antiviral effect in vivo, but rather may play a role in immune-mediated stromal inflammation, which Would explain the improvement of the clinical signs of HSK observed. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.04.011
• 作为产物：
  描述：

  (22E)-3β-bromostigmasta-5,22-diene 在 chromium(VI) oxide 、 potassium permanganate 、 硫酸 、 ferric nitrate 作用下， 以 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 3.0h， 生成 (22E)-3β-bromo-5α-hydroxystigmast-22-en-6-one
  参考文献：
  名称：

  In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues

  摘要：

  Brassinosteroids area novel group of steroids that appear to be ubiquitous in p I ants and are essential for normal plant growth and development. It has been previously reported that brassinosteroid analogues exert an antiviral activity against herpes simplex virus type 1 (HSV-1) and arenaviruses. In the present study, we report the chemical synthesis of compounds (22S,23S)-3beta-bromo-5alpha,22,23-trihydroxystigmastan-6-one (2), (22S,23S)-5alpha-fluoro-3beta-22,23-trihydroxystigmastan-6-one (3), (22S,23S)-3beta,5alpha,22,23-tetrahydroxy-stigmastan-6-one (4) as well as their antiherpetic activity both in a human conjunctive cell line (IOBA-NHC) and in the murine herpetic stromal keratitis (HSK) experimental model. All compounds prevented HSV-1 multiplication in NHC cells in a dose dependent manner when added after infection with no cytotoxicity. Administration Of Compounds 2, 3, and 4 to the eyes of mice at 1, 2, and 3 days post-infection delayed and reduced the incidence of HSK, consisting mainly of inflammation, vascularization, and necrosis, compared to untreated, infected mice. However, viral titers of eye washes showed no differences among samples from treated and untreated mice. Since the decrease in the percentage of mice with ocular lesions occurred 5 days after treatment had ended, we suggest that brassinosteroids 2, 3, and 4 did not exert a direct antiviral effect in vivo, but rather may play a role in immune-mediated stromal inflammation, which Would explain the improvement of the clinical signs of HSK observed. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.04.011

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.