litseaverticillol H

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: litseaverticillol H
• 英文别名: (4S,5R)-5-[(1E)-2,6-dimethyl-5-oxohepta-1,6-dienyl]-4-hydroxy-2-methylcyclopent-2-en-1-one
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: TZSBAFUMFLJLRE-UNZKQPITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  litseaverticillols F/G 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-oxo-litseaverticillol F/G 、 litseaverticillol H
  参考文献：
  名称：

  Natural anti-HIV agents. Part 3: Litseaverticillols A–H, novel sesquiterpenes from Litsea verticillata

  摘要：

  Bioassay directed-fractionation led to the identification of litseaverticillols A-H (1-8) from the leaves and twigs of Litsea verticillata Hance. These new sesquiterpenes possess a unique skeleton that was recently designated as 'litseane'. The structures of these compounds were determined by spectroscopic means including I D and 2D NMR data. Structural configurations were determined by ROESY experiments. Mosher ester reactions and optical rotation measurements established the sesquiterpenes 1-8 as racemates. Isolates 1-8 inhibited HIV-1 replication in HOG.R5 cells with IC50 values ranging from 2 to 15 mug/ml (8-58 muM) while affecting the growth of HOG.R5 at concentrations 2-3-fold higher. Based on this data, structure-activity relationships can be discerned, suggesting compounds of this class are good candidates for analog production. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01491-6

文献信息

• Natural anti-HIV agents. Part 3: Litseaverticillols A–H, novel sesquiterpenes from Litsea verticillata
  作者：Hong-Jie Zhang、Ghee Teng Tan、Vu Dinh Hoang、Nguyen Van Hung、Nguyen Manh Cuong、Djaja Doel Soejarto、John M Pezzuto、Harry H.S Fong

  DOI：10.1016/s0040-4020(02)01491-6

  日期：2003.1

  Bioassay directed-fractionation led to the identification of litseaverticillols A-H (1-8) from the leaves and twigs of Litsea verticillata Hance. These new sesquiterpenes possess a unique skeleton that was recently designated as 'litseane'. The structures of these compounds were determined by spectroscopic means including I D and 2D NMR data. Structural configurations were determined by ROESY experiments. Mosher ester reactions and optical rotation measurements established the sesquiterpenes 1-8 as racemates. Isolates 1-8 inhibited HIV-1 replication in HOG.R5 cells with IC50 values ranging from 2 to 15 mug/ml (8-58 muM) while affecting the growth of HOG.R5 at concentrations 2-3-fold higher. Based on this data, structure-activity relationships can be discerned, suggesting compounds of this class are good candidates for analog production. (C) 2002 Elsevier Science Ltd. All rights reserved.