(5S)-5-hydroxyeicosanoic acid lactone | 85535-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (5S)-5-hydroxyeicosanoic acid lactone
• 英文别名: (5S)-hydroxycosanoic acid δ-lactone；(5S)-5-hydroxy-eicosanoic acid δ-lactone；Meadowlactone, (S)-；(6S)-6-pentadecyloxan-2-one
• CAS: 85535-79-1
• 化学式: C₂₀H₃₈O₂
• 分子量: 310.521
• InChiKey: LLPDOHGLBDHCJZ-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2Z,5S)-hydroxycos-2-enoic acid δ-lactone 生成 (5S)-5-hydroxyeicosanoic acid lactone
  参考文献：
  名称：

  Antiparasite and antimycobacterial activity of passifloricin analogues

  摘要：

  Several structural analogues of the polyketide passifloricin lactone were synthesized using asymmetric stereoselective allylations and ring-closing methateses as key reactions. These compounds were active in vitro against intracellular amastigotes of Leishmania panamensis (strain UA 140), trophozoites of Plasinodium falciparum (strain NF54), and Mycobacterium tuberculosis (strain H(37)Rv). However, in spite of the significative antiparasitic activity of some synthetic analogues a high cytotoxicity was also observed. Based on these results a lactam derivative was also synthesized. This compound maintained a good level of activity with less toxicity. (c) 2006 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/j.tet.2006.02.017

文献信息

• Total synthesis of leukotriene E4, a member of the SRS-A family
  作者：Michael Rosenberger、Christian Newkom、Edward R. Aig

  DOI：10.1021/ja00349a052

  日期：1983.6
• Antiparasite and antimycobacterial activity of passifloricin analogues
  作者：Wilson Cardona、Winston Quiñones、Sara Robledo、Ivan Darío Vélez、Juan Murga、Jorge García-Fortanet、Miguel Carda、Diana Cardona、Fernando Echeverri

  DOI：10.1016/j.tet.2006.02.017

  日期：2006.4

  Several structural analogues of the polyketide passifloricin lactone were synthesized using asymmetric stereoselective allylations and ring-closing methateses as key reactions. These compounds were active in vitro against intracellular amastigotes of Leishmania panamensis (strain UA 140), trophozoites of Plasinodium falciparum (strain NF54), and Mycobacterium tuberculosis (strain H(37)Rv). However, in spite of the significative antiparasitic activity of some synthetic analogues a high cytotoxicity was also observed. Based on these results a lactam derivative was also synthesized. This compound maintained a good level of activity with less toxicity. (c) 2006 Elsevier Ltd. All fights reserved.