methyl 8-hydroxy-6-octynoate | 125198-11-0

• 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: methyl 8-hydroxy-6-octynoate
• 英文别名: methyl 8-hydroxyoct-6-ynoate；Methyl 8-hydroxyoct-6-ynoate
• CAS: 125198-11-0
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: KVJUAEZAORNRAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 8-hydroxy-6-octynoate 在 镍 manganese(IV) oxide 、 敌草腈 、 氢气 、 碘 作用下， 反应 32.0h， 生成 methyl (6E)-8-oxo-6-octenoate
  参考文献：
  名称：

  Design, synthesis, and 5-lipoxygenase-inhibiting properties of 1-thio-substituted butadienes

  摘要：

  The synthesis of novel 1-thio-substituted butadienes, designed as mechanism-based 5-lipoxygenase inhibitors, is described. The structure of these compounds closely resembles a proposed high-energy intermediate during the lipoxygenation of arachidonic acid. They demonstrate 5-lipoxygenase inhibition in vitro and in vivo. The most potent compound is 15a with an IC50 of 1.8 microM in vitro. LTC4 release was inhibited by 80% after intraperitoneal administration of 15c at a dose of 2 mg/kg.

  DOI：

  10.1021/jm00166a013
• 作为产物：
  描述：

  1-<4-bromobutyl>-4-ethyl-2,6,7-trioxabicyclo<2.2.2>octane 在 正丁基锂 、 lithium iodide 作用下， 反应 17.0h， 生成 methyl 8-hydroxy-6-octynoate
  参考文献：
  名称：

  Design, synthesis, and 5-lipoxygenase-inhibiting properties of 1-thio-substituted butadienes

  摘要：

  The synthesis of novel 1-thio-substituted butadienes, designed as mechanism-based 5-lipoxygenase inhibitors, is described. The structure of these compounds closely resembles a proposed high-energy intermediate during the lipoxygenation of arachidonic acid. They demonstrate 5-lipoxygenase inhibition in vitro and in vivo. The most potent compound is 15a with an IC50 of 1.8 microM in vitro. LTC4 release was inhibited by 80% after intraperitoneal administration of 15c at a dose of 2 mg/kg.

  DOI：

  10.1021/jm00166a013

文献信息

• Investigation of oxacycle formation by base-promoted endo-mode ring-closing reaction of allenes
  作者：Shinji Kitagaki、Takamasa Kawamura、Daisuke Shibata、Chisato Mukai

  DOI：10.1016/j.tet.2008.09.069

  日期：2008.12

  The base-promoted endo-mode ring closure of electron-withdrawing group-substituted allenes provided the following interesting results: (1) the endo-mode ring-closing reaction of 1-(benzyloxycarbonyl)-1-(ω-hydroxyalkyl)allenes smoothly proceeded during the formation of five-, seven-, and eight-membered rings; (2) base treatment of benzyloxycarbonylallene and sulfonylallene, having a 2-hydroxyethyl group

  吸电子基团取代的烯基的碱促进的内模闭环提供了以下有趣的结果：（1）1-（苄氧基羰基）-1-（ω-羟烷基）烯丙基的内模闭环反应平稳在形成五元，七元和八元环的过程中进行；（2）在醛的存在下，在醛的存在下，对在C-1位具有2-羟乙基的苄氧羰基烯丙基和磺酰基烯基进行碱处理，使该环闭环并与该醛缩合一锅；和（3）内通过，得到六元内酯羧酸根阴离子的内部攻击sulfonylallenes的-mode环闭合。
• Synthesis and Evaluation of Simplified Cruentaren A Analogues
  作者：Xiaozheng Dou、Bhargav A. Patel、Terin D’Amico、Chitra Subramanian、Eric Cousineau、Yi Yi、Mark Cohen、Brian S. J. Blagg

  DOI：10.1021/acs.joc.2c00948

  日期：2022.8.5

  complex structure. Herein, we systematically removed the functionalities present in fragment 2 of cruentaren A and incorporated some key structural modifications from previous work, which produced 12 simplified analogues. Our studies determined that all functional groups present in fragment 2 are essential for cruentaren A’s anticancer activity.

  90 kDa 热休克蛋白 (Hsp90) 属于一组分子伴侣，通过将新生多肽折叠成其生物活性蛋白来调节体内平衡，其中许多参与癌症的发展和进展。因此，抑制 Hsp90 是治疗癌症的一个令人兴奋的研究领域。然而，在临床试验中评估的 18 种 Hsp90 N 末端抑制剂中的大多数都表现出有害的副作用和毒性。Cruentaren A 是一种天然产物，通过破坏 Hsp90α 和 F 1 F O之间的相互作用，对各种人类癌细胞系表现出有效的抗癌活性ATP 合酶，它不会诱导促生存、热休克反应，这是与当前 Hsp90 抑制剂相关的主要限制。然而，cruentaren A作为一种新型抗癌剂的发展受到其复杂结构的阻碍。在这里，我们系统地删除了 cruentaren A 片段 2 中存在的功能，并结合了以前工作的一些关键结构修改，产生了 12 个简化的类似物。我们的研究确定片段 2 中存在的所有官能团对于 cruentaren
• Design, synthesis, and 5-lipoxygenase-inhibiting properties of 1-thio-substituted butadienes
  作者：Rudolf Hanko、Michael D. Hammond、Romanis Fruchtmann、Joerg Pfitzner、Graham A. Place

  DOI：10.1021/jm00166a013

  日期：1990.4

  The synthesis of novel 1-thio-substituted butadienes, designed as mechanism-based 5-lipoxygenase inhibitors, is described. The structure of these compounds closely resembles a proposed high-energy intermediate during the lipoxygenation of arachidonic acid. They demonstrate 5-lipoxygenase inhibition in vitro and in vivo. The most potent compound is 15a with an IC50 of 1.8 microM in vitro. LTC4 release was inhibited by 80% after intraperitoneal administration of 15c at a dose of 2 mg/kg.