2-(hexadec-2-yn-1-yloxy)tetrahydro-2H-pyran | 119290-95-8

• 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-(hexadec-2-yn-1-yloxy)tetrahydro-2H-pyran
• 英文别名: 2-Hexadec-2-ynoxyoxane
• CAS: 119290-95-8
• 化学式: C₂₁H₃₈O₂
• 分子量: 322.532
• InChiKey: SOQDRLNXWHPPRI-UHFFFAOYSA-N

物化性质

• 沸点：
  435.3±35.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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-(hexadec-2-yn-1-yloxy)tetrahydro-2H-pyran 在 重铬酸吡啶 、 copper diacetate 、 sodium hydride 、 对甲苯磺酸 、 1,3-丙二胺 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 Dotriaconta-15,17-diynedioic acid
  参考文献：
  名称：

  Synthesis of Ceramide Mimics with a Pseudo Cyclic Framework

  摘要：

  我们设计并合成了具有伪环框架的神经酰胺类似物，这些类似物可以转化为“二聚体”鞘磷脂和糖神经鞰脂，作为人工筏潜在的组成部分。这些分子的特点是具有（i）两个亲水性头部基团，（ii）共价连接的碳氢链，以及（iii）两个未固定的烷基链。神经酰胺类似物的自组装形成纳米棒的过程将简要讨论。

  DOI：

  10.1055/s-2003-42094
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 正丁基锂 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 2-(hexadec-2-yn-1-yloxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  Synthesis of novel symmetrical, single-chain, diacetylene-modified bolaamphiphiles with different alkyl chain lengths

  摘要：

  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.

  DOI：

  10.1007/s00706-010-0255-y

文献信息

• [EN] NUCLEOSIDE PRODRUGS AND USES RELATED THERETO<br/>[FR] PROMÉDICAMENTS NUCLÉOSIDIQUES ET LEURS UTILISATIONS
  申请人：UNIV EMORY

  公开号：WO2021035214A1

  公开（公告）日：2021-02-25

  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.

  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。
• ω-Functionalized Lipid Prodrugs of HIV NtRTI Tenofovir with Enhanced Pharmacokinetic Properties
  作者：Nicole Pribut、Michael D’Erasmo、Madhuri Dasari、Kyle E. Giesler、Sabrina Iskandar、Savita K. Sharma、Perry W. Bartsch、Akshay Raghuram、Anatoliy Bushnev、Soyon S. Hwang、Samantha L. Burton、Cynthia A. Derdeyn、Adriaan E. Basson、Dennis C. Liotta、Eric J. Miller

  DOI：10.1021/acs.jmedchem.1c01083

  日期：2021.9.9

  of two FDA-approved prodrugs, both of which metabolize prematurely in the liver and/or plasma. This premature prodrug processing depletes significant fractions of each oral dose and causes toxicity in kidney, bone, and liver with chronic administration. Although TFV exalidex (TXL), a phospholipid-derived prodrug of TFV, was designed to address this issue, clinical pharmacokinetic studies indicated substantial

  替诺福韦 (TFV) 是许多针对 HIV/AIDS 患者的联合抗逆转录病毒疗法中的基石核苷酸逆转录酶抑制剂 (NtRTI)。由于细胞渗透性和口服生物利用度较差，TFV 作为 FDA 批准的两种前药之一施用，这两种前药都会在肝脏和/或血浆中过早代谢。这种过早的前药加工会消耗每次口服剂量的很大一部分，并在长期给药时引起肾脏、骨骼和肝脏毒性。尽管 TFV exalidex (TXL)（一种 TFV 的磷脂衍生前药）旨在解决这个问题，但临床药代动力学研究表明大量的肝提取，将 TXL 的临床开发转向 HBV。为了规避这种代谢缺陷，我们合成并评估了 ω 功能化的 TXL 类似物，其肝稳定性显着提高。这项工作导致了化合物21和23的鉴定，它们在人肝微粒体中表现出比 TXL 更长的t 1/2值、有效的体外抗 HIV 活性以及增强的体内药代动力学特性。
• High-Stability Liposomes from Macrocyclic Diyne Phospholipids
  作者：Mladen Ladika、Thomas E. Fisk、Weishi W. Wu、Steven D. Jons

  DOI：10.1021/ja00105a076

  日期：1994.12
• Antibacterial activity of 2-alkynoic fatty acids against multidrug-resistant bacteria
  作者：David J. Sanabria-Ríos、Yaritza Rivera-Torres、Gamalier Maldonado-Domínguez、Idializ Domínguez、Camille Ríos、Damarith Díaz、José W. Rodríguez、Joanne S. Altieri-Rivera、Eddy Ríos-Olivares、Gabriel Cintrón、Nashbly Montano、Néstor M. Carballeira

  DOI：10.1016/j.chemphyslip.2013.12.006

  日期：2014.2

  The first study aimed at determining the structural characteristics needed to prepare antibacterial 2-alkynoic fatty acids (2-AFAs) was accomplished by synthesizing several 2-AFAs and other analogs in 18-76% overall yields. Among all the compounds tested, the 2-hexadecynoic acid (2-HDA) displayed the best overall antibacterial activity against Gram-positive Staphylococcus aureus (MIC = 15.6 mu g/mL), Staphylococcus saprophyticus (MIC = 15.5 mu g/mL), and Bacillus cereus (MIC = 31.3 mu g/mL), as well as against the Gram-negative Klebsiella pneumoniae (7.8 mu g/mL) and Pseudomonas aeruginosa (MIC = 125 mu g/mL). In addition, 2-HDA displayed significant antibacterial activity against methicillin-resistant S. aureus (MRSA) ATCC 43300 (MIC = 15.6 mu g/mL) and clinical isolates of MRSA (MIC = 3.9 mu g/mL). No direct relationship was found between the antibacterial activity of 2-AFAs and their critical micelle concentration (CMC) suggesting that the antibacterial properties of these fatty acids are not mediated by micelle formation. It was demonstrated that the presence of a triple bond at C-2 and the carboxylic acid moiety in 2-AFAs are important for their antibacterial activity. 2-HDA has the potential to be further evaluated for use in antibacterial formulations. (C) 2013 Elsevier Ireland Ltd. All rights reserved.
• CI(NO) spectra ofn-Alkyn-1-ols1
  作者：A. Brauner、H. Budzikiewicz

  DOI：10.1002/oms.1210180803

  日期：1983.8

  Abstractn‐Alkyn‐1‐ols show fragmentation patterns which are influenced by the length of the chain and by the relative positions of the hydroxyl group and triple bond, and which allow a localization of the site of unsaturation.