(2S)-8-(2-tetrahydropyranyloxy)-4-octyn-2-ol | 207980-41-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S)-8-(2-tetrahydropyranyloxy)-4-octyn-2-ol
• CAS: 207980-41-4
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: RHILFLFWFCBMOQ-UEWDXFNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S)-8-(2-tetrahydropyranyloxy)-4-octyn-2-ol 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以80%的产率得到(S)-oct-4-yne-1,7-diol
  参考文献：
  名称：

  Branched-chain and unsaturated 1,7-Diaminoheptane derivatives as deoxyhypusine synthase inhibitors

  摘要：

  Deoxyhypusine synthase catalyzes the first step in the posttranslational biosynthesis of the unusual amino acid hypusine [N-epsilon-(4-amino-2-hydroxybutyl)lysine] in eukaryotic translation initiation factor 5A (eIF-SA). eIF-SA and its single hypusine residue are essential for cell proliferation. Two series of 1,7-diaminoheptane derivatives were prepared and tested as inhibitors of human deoxyhypusine synthase. These include branched-chain saturated derivatives and both branched- and straight-chain unsaturated derivatives providing size and positional variation in branching and different torsional constraints. Of the branched-chain compounds, 7-amino-1-guanidinooctane (39) proved to be the most potent inhibitor in vitro (IC50, 34 nM), while 1,7-diamino-trans-hept-3-ene (20a) displayed the greatest inhibition (IC50, 0.7 mu M) among the unsaturated compounds. Compound 39 also provided effective inhibition of hypusine production in Chinese hamster ovary cells in culture. Considerations of the in vitro inhibition data reported here, along with earlier findings, allowed some speculation concerning the conformation of the substrate spermidine during its productive interaction at the active site of deoxyhypusine synthase. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)10030-x
• 作为产物：
  描述：

  2-(4-戊炔氧基)四氢-2H-吡喃 、 S-环氧丙烷 在 六甲基磷酰三胺 、 正丁基锂 作用下， 生成 (2S)-8-(2-tetrahydropyranyloxy)-4-octyn-2-ol
  参考文献：
  名称：

  Branched-chain and unsaturated 1,7-Diaminoheptane derivatives as deoxyhypusine synthase inhibitors

  摘要：

  Deoxyhypusine synthase catalyzes the first step in the posttranslational biosynthesis of the unusual amino acid hypusine [N-epsilon-(4-amino-2-hydroxybutyl)lysine] in eukaryotic translation initiation factor 5A (eIF-SA). eIF-SA and its single hypusine residue are essential for cell proliferation. Two series of 1,7-diaminoheptane derivatives were prepared and tested as inhibitors of human deoxyhypusine synthase. These include branched-chain saturated derivatives and both branched- and straight-chain unsaturated derivatives providing size and positional variation in branching and different torsional constraints. Of the branched-chain compounds, 7-amino-1-guanidinooctane (39) proved to be the most potent inhibitor in vitro (IC50, 34 nM), while 1,7-diamino-trans-hept-3-ene (20a) displayed the greatest inhibition (IC50, 0.7 mu M) among the unsaturated compounds. Compound 39 also provided effective inhibition of hypusine production in Chinese hamster ovary cells in culture. Considerations of the in vitro inhibition data reported here, along with earlier findings, allowed some speculation concerning the conformation of the substrate spermidine during its productive interaction at the active site of deoxyhypusine synthase. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)10030-x