2-octadec-17-ynoxytetrahydropyran | 1231774-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-octadec-17-ynoxytetrahydropyran
• 英文别名: 2-(octadec-17-yn-1-yloxy)tetrahydro-2H-pyran；2-octadec-17-ynoxyoxane
• CAS: 1231774-85-8
• 化学式: C₂₃H₄₂O₂
• 分子量: 350.585
• InChiKey: VVYOGQHIAUWNJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-octadec-17-ynoxytetrahydropyran 在 吡啶 、 六甲基磷酰三胺 、 正丁基锂 、 2,4,6-三异丙基苯磺酰氯 、 硫酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 76.0h， 生成 ammonium [(1R)-2-(6-aminopurin-9-yl)-1-methyl-ethoxy]methyl-(18-trimethylsilyloctadecoxy)phosphinate
  参考文献：
  名称：

  [EN] NUCLEOSIDE PRODRUGS AND USES RELATED THERETO
  [FR] PROMÉDICAMENTS NUCLÉOSIDIQUES ET LEURS UTILISATIONS

  摘要：

  揭示了具有改善代谢稳定性和口服生物利用度的非环核苷前药。一般来说，这些前药是非环核苷膦酸酯的衍生物，含有类似脂质的基团，可以增加口服吸收并在肝脏和血浆中提高稳定性。最好，类似脂质的基团可以抵抗酶介导的ω-氧化，例如细胞色素P450酶催化的ω-氧化。还揭示了非环核苷前药的药物配方。这些非环核苷前药及其药物配方可用于治疗病毒感染，如HIV感染，和/或病毒相关癌症，如HPV相关癌症。

  公开号：

  WO2021035214A1
• 作为产物：
  描述：

  乙炔钠 、 2-((16-bromohexadecyl)oxy)tetrahydro-2H-pyran 在 N,N-二甲基丙烯基脲 、 potassium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以22%的产率得到2-octadec-17-ynoxytetrahydropyran
  参考文献：
  名称：

  [EN] NUCLEOSIDE PRODRUGS AND USES RELATED THERETO
  [FR] PROMÉDICAMENTS NUCLÉOSIDIQUES ET LEURS UTILISATIONS

  摘要：

  揭示了具有改善代谢稳定性和口服生物利用度的非环核苷前药。一般来说，这些前药是非环核苷膦酸酯的衍生物，含有类似脂质的基团，可以增加口服吸收并在肝脏和血浆中提高稳定性。最好，类似脂质的基团可以抵抗酶介导的ω-氧化，例如细胞色素P450酶催化的ω-氧化。还揭示了非环核苷前药的药物配方。这些非环核苷前药及其药物配方可用于治疗病毒感染，如HIV感染，和/或病毒相关癌症，如HPV相关癌症。

  公开号：

  WO2021035214A1

文献信息

• Synthesis of novel symmetrical, single-chain, diacetylene-modified bolaamphiphiles with different alkyl chain lengths
  作者：Simon Drescher、Katrin Helmis、Andreas Langner、Bodo Dobner

  DOI：10.1007/s00706-010-0255-y

  日期：2010.3

  General syntheses of novel symmetrical, single-chain, diacetylene-modified bolaphospholipids have been carried out in five steps. For the omega-alkynols, which have an important role as key intermediates, three different synthetic approaches were comprehensively investigated. For the final synthesis it is suggested that (1) alkylation of lithium (trimethylsilyl)acetylide with tetrahydropyranyl-protected omega-bromoalcohols, followed by (2) cleavage of the trimethylsilyl moiety and the tetrahydropyranyl protecting group, and (3) copper(II)-catalyzed Eglinton coupling is the best strategy for obtaining diacetylene-modified alkane-1,omega-diols, because higher yields were obtained while avoiding the formation of by-products. Moreover, conversion of the diols into bipolar phospholipids was achieved by bis-phosphorylation with beta-bromoethylphosphoric acid dichloride and subsequent quaternization with trimethylamine or dimethylamine. Finally, spectral data are presented for novel single-chain, diacetylene-modified bolaphospholipids with promising potential as starting molecules in the formation of polymerizable and, thus, thermostable nanofibers.
• NUCLEOSIDE PRODRUGS AND USES RELATED THERETO
  申请人：Emory University

  公开号：EP4017499A1

  公开（公告）日：2022-06-29
• Nucleoside Prodrugs and Uses Related Thereto
  申请人：Emory University

  公开号：US20220298185A1

  公开（公告）日：2022-09-22

  Disclosed are acyclic nucleoside prodrugs with improved metabolic stability and oral bioavailability. In general, the prodrugs are derivatives of acyclic nucleoside phosphonates containing a lipid-like moiety that can increase oral absorption and subsequent stability in the liver and plasma. Preferably, the lipid-like moiety can resist enzyme-mediated ω-oxidation, such as ω-oxidation catalyzed by cytochrome P450 enzymes. Also disclosed are pharmaceutical formulations of the acyclic nucleoside prodrugs. The acyclic nucleoside prodrugs and pharmaceutical formulations thereof can be used to treat viral infections, such as HIV infections, and/or viral-associated cancer, such as HPV-associated cancers.