typhasterol | 87734-68-7

• 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: typhasterol
• 英文别名: (3R,5S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-3-hydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• CAS: 87734-68-7
• 化学式: C₂₈H₄₈O₄
• 分子量: 448.687
• InChiKey: SBSXXCCMIWEPEE-SELDZKRUSA-N

物化性质

• 熔点：
  138 °C
• 沸点：
  133-134 °C
• 密度：
  1.080±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 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：

  (22R,23R,24S)-3β-bromo-22,23-diacetoxy-5α-ergostan-6-one 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 为溶剂， 反应 29.0h， 生成 typhasterol
  参考文献：
  名称：

  Aburatani, Masakazu; Takeuchi, Tadashi; Mori, Kenji, Agricultural and Biological Chemistry, 1987, vol. 51, # 7, p. 1909 - 1914

  摘要：

  DOI：

文献信息

• Stereoselective synthesis of plant growth-prompting steroids, brassinolide, castasterone, typhasterol, and their 28-nor analogues
  作者：Suguru Takatsuto、Naoto Yazawa、Masaji Ishiguro、Masuo Morisaki、Nobuo Ikekawa

  DOI：10.1039/p19840000139

  日期：——

  Plant growth-promoting steroids, brassinolide (1a), (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one, castasterone (2a), (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-5α-ergo-stan-6-one, 28-norbrassinolide (1b), (22R,23R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-chole-stan-6-one, brassinone (2b), (22R,23R)-2α,3α,22,23-tetrahydroxy-5α-cholestan-6-one, and typh-asterol (2c), (22R,23R,24S)-3α

  促进植物生长的类固醇，油菜素内酯（1a），（22 R，23 R，24 S）-2α，3α，22,23-四羟基-B -homo-7-oxa-5α-ergostan-6-one，卡司他酮（ 2a），（22 R，23 R，24 S）-2α，3α，22,23-四羟基-5α-麦角甾烷-6-一，28-去甲油菜素内酯（1b），（22 R，23 R）-2α ，3α，22,23-tetrahydroxy- B -homo-7-oxa-5α-hole-stan-6-，brasinone（2b），（22 R，23 R）-2α，3α，22,23-tetrahydroxy- 5α-胆甾醇-6-1和伤寒甾醇（2c），（22 R，23 R，24 S）-3α，22,23-三羟基-5α.-麦角甾醇-6-，已被立体选择性地合成。这些类固醇在三种不同的生物测定法中显示出非常强的生物学活性。
• Stereoselective synthesis of the brassinolide side chain; novel syntheses of brassinolide and related compounds
  作者：Zhou Wei-shan、Jiang Biao、Pan Xin-fu

  DOI：10.1016/s0040-4020(01)85457-0

  日期：1990.1

  A stereoselective synthesis of the brassinolide side chain involves the lactonization of Z-10 under acidic condition to give an α,β-unsa-turated-δ-lactone 11 with the inversion of the configuration at C-22 of the epoxy steroid in quantitative yield. The 22R,23R,24S-γ-hydroxy-δ-lactone 14 was used as key intermediate for the syntheses of brassinolide(1), homobrassinolide(2), and typhasterol(4) as well

  芸苔素内酯侧链的立体选择性合成涉及在酸性条件下Z- 10的内酯化，得到α，β-不饱和的-δ-内酯11，且环氧甾类化合物在C-22处的构型以定量产率转化。的22R，23R，24S-γ羟基δ内酯14被用作关键中间体为油菜素内酯（的合成1），高油菜素内酯（2），和typhasterol（4）以及所述dolicholide的侧链（3）。
• A novel synthesis of brassinolide and related compounds
  作者：Zhou Wei-Shan、Biao Jiang、Xin-fu Pan

  DOI：10.1039/c39890000612

  日期：——

  A stereoselective synthesis of the natural promoting steroids, brassinolide, homobrassinolide, and typhasterol is described, which involves construction of a side chain by lactonisation of Z-(5) under acidic conditions to give an α,β-unsaturated δ-lactone (6) with the inversion of the configuration at C-22 of the epoxy steroid in quantitative yield.

  描述了天然促进类固醇，油菜素内酯，高油菜素内酯和秋黄甾醇的立体选择性合成，该合成涉及在酸性条件下通过Z-（5）的内酯化构建侧链，得到α，β-不饱和δ-内酯（6）以定量收率将环氧类固醇的C-22处的构型反转。
• Study on the synthesis of brassinolide and related compounds III
  作者：Wei-Shan Zhou、Wei-Sheng Tian

  DOI：10.1016/s0040-4020(01)86858-7

  日期：1987.1

  was synthesized stereoselectively from hyodeoxycholic acid 3. The aldehyde 5 derived from 3 was reacted with the anion of 3-methylbutenolide under kinetic condition to afford (22R,23R)-7 as the major product. Hydrogenation of 7 and its 22-acetate 14 over PtO2-Pt/C yielded the expected compound 8 and 15, respectively, in very good yield. Typhasterol was obtained from 8 and 15 through the following sequence

  从猪去氧胆酸3立体合成了酪甾醇2。在动力学条件下，使衍生自3的醛5与3-甲基丁烯内酯的阴离子反应，得到（22R，23R）-7为主要产物。在PtO 2 -Pt / C上氢化7及其22-乙酸酯14分别以非常好的收率分别得到预期的化合物8和15。通过以下反应步骤8 → 9 → 10 → 12 → 13 →从八和十五获得邻苯三酚2和15 → 16 → 17 → 13 → -2。
• Compositions and methods for targeted enzymatic release of cell regulatory compounds
  申请人：Naleway J. John

  公开号：US20060105915A1

  公开（公告）日：2006-05-18

  Novel pro-drugs and methods for their use to alter the growth and biological characteristics of living cells, tissues, or whole organisms are described. The methods allow for selective activation of the pro-drugs at or near transformant host cells expressing a gene for an enzyme that activates the pro-drugs. Pro-drugs according to a preferred embodiment of the invention are conjugates of a bioactive compound and a chemical group that is capable of being cleaved from the bioactive compound by action of an enzyme. Methods according to this invention include, (a) introducing into targeted cells a gene encoding an enzyme and (b) administering a pro-drug, wherein the enzyme releases the pro-drug from conjugation. In a preferred embodiment of the invention, the gene encoding the enzyme is a marker gene.

  本发明描述了新型前药及其使用方法，用于改变活细胞、组织或整个生物的生长和生物学特征。该方法允许在表达激活前药酶基因的转化宿主细胞处或其附近选择性地激活前药。根据本发明的首选实施例，前药是生物活性化合物和可被酶作用从生物活性化合物中裂解的化学基团的结合物。根据本发明的方法包括：（a）将编码酶的基因引入靶向细胞中；（b）给予前药，其中酶释放结合的前药。在本发明的首选实施例中，编码酶的基因是标记基因。