丙炔基-PEG3-溴 | 203740-63-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 丙炔基-PEG3-溴
• 英文名称: 3-(2-(2-(2-bromoethoxy)ethoxy)ethoxy)prop-1-yne
• 英文别名: Propargyl-PEG3-Bromide；3-[2-[2-(2-bromoethoxy)ethoxy]ethoxy]prop-1-yne
• CAS: 203740-63-0
• 化学式: C₉H₁₅BrO₃
• 分子量: 251.12
• InChiKey: UIGSOGCOFXYRNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 储存条件：
  储存温度应保持在2-8°C，需要密封并置于干燥处。

制备方法与用途

propargyl-PEG3-bromide 是一种PROTAC连接子，属于PEG类化合物，可用于合成PROTAC分子。

反应信息

• 作为反应物：
  描述：

  丙炔基-PEG3-溴 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 二甲基亚砜 为溶剂， 反应 35.0h， 生成 2-amino-5-(1-[2-[2-(2-[3-[1-(2,6-dioxopiperidin-3-yl)-3-methyl-2-oxo-1,3-benzodiazol-5-yl]propoxy]ethoxy)ethoxy]ethyl]pyrazol-4-yl)pyridine-3-carboxylic acid
  参考文献：
  名称：

  [EN] MERTK DEGRADERS AND USES THEREOF
  [FR] AGENTS DE DÉGRADATION DE MERTK ET LEURS UTILISATIONS

  摘要：

  本发明提供了化合物、其组合物以及使用相同的方法。

  公开号：

  WO2020010210A1
• 作为产物：
  描述：

  三乙二醇单(2-丙炔基)醚 在 四溴化碳 作用下， 以 二氯甲烷 为溶剂， 以89 %的产率得到丙炔基-PEG3-溴
  参考文献：
  名称：

  利用光氧化还原催化和流动化学从烷基溴和醇制备烷基磺酰氟的温和策略

  摘要：

  容易获得含有磺酰氟基团的富含sp 3的支架仍然受到限制。在此，我们描述了一种温和且可扩展的策略，利用光氧化还原催化从容易获得的烷基溴和醇制备烷基磺酰氟。该方法基于卤素原子转移(XAT)，然后是SO 2捕获和氟化。该方法的特点是条件温和，能够快速获得高价值衍生物，并且已使用连续搅拌釜级联反应器将产量扩大至 5 g。

  DOI：

  10.1021/acs.orglett.4c01216

文献信息

• [EN] COMPOSITIONS AND METHODS RELATED TO MOLECULAR CONJUGATION<br/>[FR] COMPOSITIONS ET PROCÉDÉS ASSOCIÉS À LA CONJUGAISON MOLÉCULAIRE
  申请人：INTOCELL INC

  公开号：WO2021111185A1

  公开（公告）日：2021-06-10

  The invention relates to activated Michael acceptor (AMA) compounds that can undergo conjugation with biomolecules containing Michael donor moieties, thereby providing plasma-stable antibody-drug conjugates (ADCs). Pharmaceutical compositions of the ADCs are disclosed as well. Also provided herein are a number of applications (e.g., therapeutic applications) in which the compositions are useful.

  这项发明涉及可以与含有Michael供体基团的生物分子发生共轭反应的活化Michael受体（AMA）化合物，从而提供稳定的血浆抗体药物偶联物（ADCs）。还公开了ADCs的药物组合物。本文还提供了一些应用（例如治疗应用），其中这些组合物是有用的。
• Synthesis of Gb ₃ Glycosphingolipids with Labeled Head Groups: Distribution in Phase‐Separated Giant Unilamellar Vesicles
  作者：Jeremias Sibold、Katharina Kettelhoit、Loan Vuong、Fangyuan Liu、Daniel B. Werz、Claudia Steinem

  DOI：10.1002/anie.201910148

  日期：2019.12.2

  sphingosine backbone. The synthetic Gb3 glycosphingolipids were reconstituted into coexisting liquid-ordered (lo )/liquid-disordered (ld ) giant unilamellar vesicles (GUVs), and STx binding was verified by fluorescence microscopy. Gb3 with the C24:0 fatty acid partitioned mostly in the lo phase, while the unsaturated C24:1 fatty acid distributes more into the ld phase. The α-hydroxylation does not influence

  受体脂质Gb3负责将志贺毒素（STx）特异性内化到细胞中。Gb3的头基定义了STx结合的特异性，并且具有不同脂肪酸的主链有望影响其在膜内的定位，从而影响膜的组织和蛋白质的内在化。为了研究这种影响，合成了一组标有BODIPY荧光团标记在头部基团上的Gb3糖鞘脂。将C24脂肪酸，饱和的，不饱和的，α-羟基化的衍生物及其组合连接至鞘氨醇主链。合成的Gb3糖鞘脂被重构为共存的液体有序（lo）/液体无序（ld）巨型单层囊泡（GUVs），并通过荧光显微镜验证了STx的结合。带有C24的Gb3：0脂肪酸主要在lo相中分配，而不饱和C24：1脂肪酸则更多地分配到ld相中。α-羟基化不影响其分配。
• Generation of Clickable Pittsburgh Compound B for the Detection and Capture of β-Amyloid in Alzheimer’s Disease Brain
  作者：Ian Diner、Jeromy Dooyema、Marla Gearing、Lary C. Walker、Nicholas T. Seyfried

  DOI：10.1021/acs.bioconjchem.7b00500

  日期：2017.10.18

  The benzothiazole-aniline derivative Pittsburgh Compound B (PiB) is the prototypical amyloid affinity probe developed for the in vivo positron emission tomography (PET) detection of amyloid beta (Aβ) deposits in Alzheimer’s disease (AD). Specific high-affinity binding sites for PiB have been found to vary among AD cases with comparable Aβ load, and they are virtually absent on human-sequence Aβ deposits

  苯并噻唑-苯胺衍生物匹兹堡化合物B（PiB）是原型淀粉样蛋白亲和探针，用于体内正电子发射断层扫描（PET）检测阿尔茨海默氏病（AD）中的淀粉样β（Aβ）沉积物。已经发现，PiB的特异性高亲和力结合位点在具有相似的Aβ负荷的AD病例之间变化，并且在动物模型中的人序列Aβ沉积物上实际上不存在，它们都没有发展出AD的完整表型。因此，PiB可能是研究Aβ病理生物学的有益探针，但对PiB结合在分子或结构水平上的定位知之甚少。通过用PEG 3功能化PiB的6-羟基位置间隔基和末端炔烃（炔丙基）部分，我们开发了一种可点击的PiB化合物，该化合物可通过使用铜催化的叠氮化物-炔烃环加成反应，与市售的叠氮化物标记的荧光团或亲和标签进行衍生化，通常称为“点击”化学。我们已经确定，可点击的PiB衍生物及其荧光标记的缀合物对于合成Aβ聚集体均具有较低的纳摩尔结合亲和力。此外，荧光-PiB缀合物可以有效地结合人AD脑
• Structure–Activity Relationship Studies To Identify Affinity Probes in Bis-aryl Sulfonamides That Prolong Immune Stimuli
  作者：Michael Chan、Fitzgerald S. Lao、Paul J. Chu、Jonathan Shpigelman、Shiyin Yao、Jason Nan、Fumi Sato-Kaneko、Vicky Li、Tomoko Hayashi、Maripat Corr、Dennis A. Carson、Howard B. Cottam、Nikunj M. Shukla

  DOI：10.1021/acs.jmedchem.9b00870

  日期：2019.11.14

  Agents that safely induce, enhance, or sustain multiple innate immune signaling pathways could be developed as potent vaccine adjuvants or coadjuvants. Using high-X throughput screens with cell-based nuclear factor kappa B (NF-kappa B) and interferon stimulating response element (ISRE) reporter assays, we identified a bis-aryl sulfonamide bearing compound 1 that demonstrated sustained NF-kappa B and ISRE activation after a primary stimulus with lipopolysaccharide or interferon-alpha, respectively. Here, we present systematic structure-activity relationship (SAR) studies on the two phenyl rings and amide nitrogen of the sulfonamide group of compound 1 focused toward identification of affinity probes. The murine vaccination studies showed that compounds 1 and 33 when used as coadjuvants with monophosphoryl lipid A (MPLA) showed significant enhancement in antigen ovalbumin-specific immunoglobulin responses compared to MPLA alone. SAR studies pointed to the sites on the scaffold that can tolerate the introduction of aryl azide, biotin, and fluorescent rhodamine substituents to obtain several affinity and photoaffinity probes which will be utilized in concert for future target identification and mechanism of action studies.
• Organic metal-complexes. XXI. Synthesis and structure of 3,5,15,17-tetraoxo-1,7,10,13,19,22-hexaoxa-cyclotetracosane and 2,12,14,24-tetraoxo-4,7,10,16,19,22-hexaoxa-25-mercurato-bicyclo[11.11.1]pentacosane
  作者：Wolfram V. Eichinger、Hans Musso、Klaus D. Eichhorn、G�nter Mattern

  DOI：10.1002/prac.19983400207

  日期：——

  A new synthesis of the title crown via isoxazolo crown ether 7 and macrocyclic bis-peneaminoketone 10 is described. 7 can be synthesized in 14% yield by a non-template double-[3+2] cycloaddition of dinitrileoxide 5 prepared in situ from dinitropolyether 19 by dehydration with Ph-NCO and alkyne 6. The compounds 16, 17 and 18 are synthesized by the same synthetic strategy. Comparable IR and H-1 NMR spectroscopic data of macrocyclic and non-cyclic compounds show, that macrocyclic conformation stabilizing effects can be ruled out. The structures of the macrocycles 1, 7, 10 and that of the Hg(II)-complex 25, synthesized by reaction of 1 with Hg(OAc)(2) were established by single-crystal X-ray structure analyses. Both inter-and intramolecular hydrogen bonds are observed for the macrocyclic bis-beta-eneaminoketone 10, whereas only intramolecular hydrogen bonds are formed by 1. In the Hg(II)-complex of 1 the mercury is bonded to two methylene groups. C-Hg-C is almost linear [177(1)degrees], the mean Hg-C distance amounts to 215(1) pm. In addition to the Hg-C bonds, each Hg makes a short contact to a carbonyl oxygen in a neighbouring molecule in the plane perpendicular to the C-Hg-C axis [Hg(1)-O(1) = 279(1) pm, Hg(2)-O(5)= 284(1) pm].