3-keto-22-epi-28-nor-cathasterone | 1242543-43-6

• 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: 3-keto-22-epi-28-nor-cathasterone
• 英文别名: (5S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,4,5,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6-dione
• CAS: 1242543-43-6
• 化学式: C₂₇H₄₄O₃
• 分子量: 416.645
• InChiKey: NYZFLRDFXVCLQW-GUPLTDBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-keto-22-epi-28-nor-cathasterone 、 (S)-(+)-alpha-甲氧基苯乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 5.0h， 以44.9%的产率得到(2S,3R)-2-((5S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3,6-dioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methylheptan-3-yl (S)-2-methoxy-2-phenylacetate
  参考文献：
  名称：

  3-Keto-22-epi-28-nor-cathasterone, a brassinosteroid-related metabolite from Cystoseira myrica

  摘要：

  Bioassay-guided purification of an ethanolic extract of Cystoseira myrica against HEPG-2 (liver) and HCT116 (colon) human cancer cell lines led to the isolation of 3-keto-22-epi-28-nor-cathasterone, I and cholest-4-ene-3,6-dione, 2. This finding allowed us to report for the first time that a brassinosteroid-related metabolite occurs in seaweed. These compounds showed activity in the range of 12.38-1.16 mu M with selective activity of compound 2 to liver cancer cell lines. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.06.008

文献信息

• 3-Keto-22-epi-28-nor-cathasterone, a brassinosteroid-related metabolite from Cystoseira myrica
  作者：Abdel-Hamid A. Hamdy、Elsayed A. Aboutabl、Somayah Sameer、Ahmed A. Hussein、Ana R. Díaz-Marrero、José Darias、Mercedes Cueto

  DOI：10.1016/j.steroids.2009.06.008

  日期：2009.11

  Bioassay-guided purification of an ethanolic extract of Cystoseira myrica against HEPG-2 (liver) and HCT116 (colon) human cancer cell lines led to the isolation of 3-keto-22-epi-28-nor-cathasterone, I and cholest-4-ene-3,6-dione, 2. This finding allowed us to report for the first time that a brassinosteroid-related metabolite occurs in seaweed. These compounds showed activity in the range of 12.38-1.16 mu M with selective activity of compound 2 to liver cancer cell lines. (C) 2009 Elsevier Inc. All rights reserved.