丙炔基-PEG6-甲基磺酸酯 | 1036204-62-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: 丙炔基-PEG6-甲基磺酸酯
• 英文名称: Propargyl-PEG6-Ms
• 英文别名: 2-[2-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]ethoxy]ethyl methanesulfonate
• CAS: 1036204-62-2
• 化学式: C₁₄H₂₆O₈S
• 分子量: 354.422
• InChiKey: QIFZLEBUWOVSTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  23
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  丙炔基-PEG6-甲基磺酸酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 对甲苯磺酸 、 三乙胺 作用下， 以 丙酮 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  C2 ‐linked alkynyl poly‐ethylene glycol( PEG ) adenosine conjugates as water‐soluble adenosine receptor agonists

  摘要：

  AbstractA series of 12 novel polyethylene‐glycol(PEG)‐alkynyl C2‐adenosine(ADN) conjugates were synthesized using a robust Sonogashira coupling protocol and characterized by NMR spectroscopy and mass spectrometry analysis. The ADN‐PEG conjugates showed null to moderate toxicity in murine macrophages and 12c was active against Mycobacterium aurum growth (MIC = 62.5 mg/L). The conjugates were not active against Mycobacterium bovis BCG. Conjugates 10b and 11b exhibited high water solubility with solubility values of 1.22 and 1.18 mg/ml, respectively, in phosphate buffer solutions at pH 6.8. Further, 10b and 11b induced a significant increase in cAMP accumulation in RAW264.7 cells comparable with that induced by adenosine. Analogues 10c, 11c and 12c were docked to the A1, A2A, A2B and A3 adenosine receptors (ARs) using crystal‐structures and homology models. ADN‐PEG‐conjugates bearing chains with up to five ethyleneoxy units could be well accommodated within the binding sites of A1, A2A and A3 ARs. Docking studies showed that compound 10b and 11b were the best A2A receptor binders of the series, whereas 12c was the best binder for A1 AR. In summary, introduction of hydrophilic PEG substituents at the C2 of adenine ring significantly improved water solubility and did not affect AR binding properties of the ADN‐PEG conjugates.

  DOI：

  10.1111/cbdd.14128
• 作为产物：
  描述：

  羟丙基淀粉磷酸酯 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 4.0h， 生成 丙炔基-PEG6-甲基磺酸酯
  参考文献：
  名称：

  C2 ‐linked alkynyl poly‐ethylene glycol( PEG ) adenosine conjugates as water‐soluble adenosine receptor agonists

  摘要：

  AbstractA series of 12 novel polyethylene‐glycol(PEG)‐alkynyl C2‐adenosine(ADN) conjugates were synthesized using a robust Sonogashira coupling protocol and characterized by NMR spectroscopy and mass spectrometry analysis. The ADN‐PEG conjugates showed null to moderate toxicity in murine macrophages and 12c was active against Mycobacterium aurum growth (MIC = 62.5 mg/L). The conjugates were not active against Mycobacterium bovis BCG. Conjugates 10b and 11b exhibited high water solubility with solubility values of 1.22 and 1.18 mg/ml, respectively, in phosphate buffer solutions at pH 6.8. Further, 10b and 11b induced a significant increase in cAMP accumulation in RAW264.7 cells comparable with that induced by adenosine. Analogues 10c, 11c and 12c were docked to the A1, A2A, A2B and A3 adenosine receptors (ARs) using crystal‐structures and homology models. ADN‐PEG‐conjugates bearing chains with up to five ethyleneoxy units could be well accommodated within the binding sites of A1, A2A and A3 ARs. Docking studies showed that compound 10b and 11b were the best A2A receptor binders of the series, whereas 12c was the best binder for A1 AR. In summary, introduction of hydrophilic PEG substituents at the C2 of adenine ring significantly improved water solubility and did not affect AR binding properties of the ADN‐PEG conjugates.

  DOI：

  10.1111/cbdd.14128

文献信息

• Synthesis of fluorescent probes based on stilbenes and diphenylacetylenes targeting β-amyloid plaques
  作者：Ajit K. Parhi、Mei-Ping Kung、Karl Ploessl、Hank F. Kung

  DOI：10.1016/j.tetlet.2008.03.130

  日期：2008.5

  Three fluorescent probes were synthesized aiming for optical imaging to detect amyloid plaques present in patients with Alzheimer's disease (AD). These compounds were prepared via Sonogashira coupling of a well-defined fluorophore (4-bora-3a, 4a-diaza s-indacene, BODIPY) with the pharmacophore possessing either a stilbene or a diphenylacetylene moiety. Different polyethylene glycol chain lengths were

  合成了三种荧光探针，旨在进行光学成像以检测阿尔茨海默病 (AD) 患者中存在的淀粉样蛋白斑块。这些化合物是通过定义明确的荧光团（4-bora-3a，4a-二氮杂茚，BODIPY）与具有二苯乙烯或二苯乙炔部分的药效团的 Sonogashira 偶联制备的。不同的聚乙二醇链长被用作荧光团和药效团之间的接头，以调整这些探针的亲脂性。这些化合物在 665-680 nm 之间表现出强烈的荧光发射，并且具有与母体荧光团 BODIPY 染料相当的非常高的消光系数。