3-(3-(3-(prop-2-ynyloxy)-2,2-bis((prop-2-inyloxy)methyl)propoxy)-2,2-bis((prop-2-ynyloxy)methyl)propoxy)prop-1-yne

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-(3-(prop-2-ynyloxy)-2,2-bis((prop-2-inyloxy)methyl)propoxy)-2,2-bis((prop-2-ynyloxy)methyl)propoxy)prop-1-yne
• 英文别名: hexapropinyloxymethyl bispentaerythritol；3-(3-(prop-2-yn-1-yloxy)-2-((3-(prop-2-yn-1-yloxy)-2,2-bis((prop-2-yn-1yloxy)methyl)propoxy)methyl)-2-((prop-2-yn-1-yloxy)methyl)propoxy)prop-1-yne；2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol hexakis(2-propynyl) ether；1,3-Bis(prop-2-ynoxy)-2-[[3-prop-2-ynoxy-2,2-bis(prop-2-ynoxymethyl)propoxy]methyl]-2-(prop-2-ynoxymethyl)propane；1,3-bis(prop-2-ynoxy)-2-[[3-prop-2-ynoxy-2,2-bis(prop-2-ynoxymethyl)propoxy]methyl]-2-(prop-2-ynoxymethyl)propane
• 化学式: C₂₈H₃₄O₇
• 分子量: 482.574
• InChiKey: OTMLOMCJTRUZIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  35
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(3-(3-(prop-2-ynyloxy)-2,2-bis((prop-2-inyloxy)methyl)propoxy)-2,2-bis((prop-2-ynyloxy)methyl)propoxy)prop-1-yne 、 2-(2-叠氮乙氧基)乙醇 在 copper(II) sulfate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以74%的产率得到
  参考文献：
  名称：

  Multimeric xanthates as carbonic anhydrase inhibitors

  摘要：

  The field of multivalent inhibition of enzymes is growing exponentially from the first reported multivalent effect on a glycosidase enzyme. However, the investigations have generally remained restricted to carbohydrate-processing enzymes. Carbonic anhydrases are ubiquitous metallo-enzymes involved in many key biological processes, that catalyze the reversible hydration/dehydration of CO2/HCO3-. This study reports the first synthesis of multimeric xanthates addressing the selectivity and potency of CA multivalent inhibition. Six multivalent compounds containing three, four, and six xanthate moieties were prepared and assayed against four relevant CA isoforms together with their monovalent analogues. Some of the multimers were stronger inhibitors than the monomeric species. For hCA I, the two best molecules 18 and 20 showed an improvement of the ligand affinity of 4.8 and 2.3 per xanthate units (valence-corrected values), respectively, which corresponds to a clear multivalent effect. Moreover, the biochemical assays demonstrated that the multimeric presentation of xanthates, also affected the selectivity of the relative inhibition among the four CAs assayed.

  DOI：

  10.3109/14756366.2015.1072177
• 作为产物：
  描述：

  双季戊四醇 、 3-溴丙炔 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 水 、 甲苯 为溶剂， 反应 17.0h， 以33%的产率得到3-(3-(3-(prop-2-ynyloxy)-2,2-bis((prop-2-inyloxy)methyl)propoxy)-2,2-bis((prop-2-ynyloxy)methyl)propoxy)prop-1-yne
  参考文献：
  名称：

  簇状糖苷和杂糖簇以替代排列形式呈现

  摘要：

  多价碳水化合物或糖簇是研究聚糖-凝集素和聚糖-酶识别过程的有用工具，具有广泛的潜在治疗应用价值。在本文中，我们报告了通过交替通过C-1，C-2，C-3或C-6糖位置偶联并使用四价和六价支架进行多价展示的新型糖簇的合成，其结构呈交替排列形式。适当的叠氮化物官能化的d-吡喃葡萄糖单元与炔基化的五-或二-五聚赤藓糖醇中央核的偶联通过铜催化的叠氮化物-炔烃环加成反应（CuAAC），可产生8个四价和六价糖团簇，收率很好（52-83％）。单击化学策略已扩展到使用三（羟甲基）-氨基甲烷（TRIS）中心支架制备四个杂糖簇。掺入一个单元的常规1-脱氧-d - nojirymicin亚氨基糖或其C-5表位异构体1 - gulo异构体以及通过C-1或C-6连接的三个d-吡喃葡萄糖单元。

  DOI：

  10.1016/j.tetlet.2018.10.069

文献信息

• Synthesis of Dendritic Glycoclusters and Their Applications for Supramolecular Gelation and Catalysis
  作者：Guijun Wang、Dan Wang、Jonathan Bietsch、Anji Chen、Pooja Sharma

  DOI：10.1021/acs.joc.0c01978

  日期：2020.12.18

  as ligands in copper-catalyzed azide and alkyne cycloaddition (CuAAC) reactions were studied. The compounds with a lower number of branches exhibit excellent gelation properties and can function as supramolecular gelators. The resulting gels were characterized using optical microcopy and atomic force microscopy. The glycoconjugates containing six branches showed significant catalytic activity for copper

  设计，合成和表征了具有三个，四个和六个分支的糖基三唑的糖簇。研究了这些分子的自组装性质及其作为配体在铜催化的叠氮化物和炔烃环加成（CuAAC）反应中的催化活性。具有较低支链数的化合物表现出优异的胶凝特性，并且可以用作超分子胶凝剂。使用光学显微镜和原子力显微镜对所得的凝胶进行表征。含有六个分支的糖缀合物对硫酸铜介导的环加成反应显示出显着的催化活性。在水溶液中，至底物的1mol％糖簇有效地促进了这些反应。发现几种三聚化合物能够与催化活性六聚化合物形成共凝胶。使用由糖缀合物形成的有机凝胶作为超分子催化剂，证明了对几种CuAAC反应的有效催化作用。CuSO金属盐还制备了4个凝胶柱，可重复使用几次以进行环加成反应。这些包括制备一些糖基三唑，芳基三唑和异恶唑。我们期望这些基于糖的软生物材料将具有超分子催化以外的铜催化环加成反应的应用。它们也可用作其他金属离子催化的有机反应的配体或凝胶基质。
• [EN] SELECTIN OR GALECTIN ANTAGONISTS FOR TREATING CYTOKINE RELEASE SYNDROME AND CRS-INDUCED NEUROTOXICITY<br/>[FR] ANTAGONISTES DE LA SÉLECTINE OU DE LA GALECTINE POUR LE TRAITEMENT DU SYNDROME DE LIBÉRATION DE LA CYTOKINE ET DE LA NEUROTOXICITÉ INDUITE PAR LE CRS
  申请人：MAGNANI JOHN L

  公开号：WO2020150263A1

  公开（公告）日：2020-07-23

  Methods and compounds for the treatment and/or prevention of CRS and/or CRS-induced neurotoxicities using at least one selectin antagonist are disclosed. The disclosed methods and compounds use at least one of the disclosed antagonists to target and reduce cytokine expression and/or endothelial activation to treat and/or prevent CRS and/or CRS-related conditions such as CRS-induced neurotoxicities.

  使用至少一种选择素拮抗剂治疗和/或预防CRS和/或CRS诱导的神经毒性的方法和化合物被披露。披露的方法和化合物使用至少一种披露的拮抗剂来靶向和减少细胞因子表达和/或内皮活化，以治疗和/或预防CRS和/或CRS相关症状，如CRS诱导的神经毒性。
• [EN] GALACTOSE-LINKED MULTIMERIC GLYCOMIMETIC INHIBITORS OF E-SELECTINS, GALECTIN-3, AND/OR CXCR4 CHEMOKINE RECEPTORS<br/>[FR] INHIBITEURS GLYCOMIMÉTIQUES MULTIMÈRES LIÉS AU GALACTOSE DE SÉLECTINES E, DE GALECTINE-3 ET/OU DE RÉCEPTEURS DE CHIMIOKINE CXCR4
  申请人：GLYCOMIMETICS INC

  公开号：WO2020219417A1

  公开（公告）日：2020-10-29

  Compounds, compositions, and methods for treating and/or preventing at least one disease, disorder, and/or condition associated with E-selectin, galectin-3, and/or CXCR4 chemokine receptor activity are disclosed herein. For example, multimeric glycomimetic inhibitors ofE-selectins, galectin-3, and/or CXCR4 chemokine receptors and their use for treating and/or preventing inflammatory diseases, fibrosis, and cancers are disclosed. Formula (I).

  本文揭示了用于治疗和/或预防与E-选择素、galectin-3和/或CXCR4趋化因子受体活性相关的至少一种疾病、紊乱和/或状况的化合物、组合物和方法。例如，本文揭示了用于治疗和/或预防炎症性疾病、纤维化和癌症的E-选择素、galectin-3和/或CXCR4趋化因子受体的多聚糖类似物抑制剂及其用途。公式（I）。
• Targeting Bacterial Biofilm: A New LecA Multivalent Ligand with Inhibitory Activity
  作者：Alessandro Palmioli、Paola Sperandeo、Alessandra Polissi、Cristina Airoldi

  DOI：10.1002/cbic.201900383

  日期：2019.12.2

  antibiotic therapies. Infections caused by Pseudomonas aeruginosa are of great concern, especially for immunocompromised and cystic fibrosis patients. P. aeruginosa lectins LecA and LecB are virulence factors and play a key role in establishing biofilm; therefore, inhibition of the function of these proteins has potential in dismantling the bacterium from the protective biofilm environment and in restoring

  细菌性病原体形成生物膜是慢性感染的标志，并与增加的抗生素耐受性有关，这使得病原体难以通过常规抗生素疗法根除。铜绿假单胞菌引起的感染引起了极大的关注，特别是对于免疫功能低下和囊性纤维化患者。铜绿假单胞菌凝集素LecA和LecB是毒力因子，在建立生物膜中起关键作用。因此，抑制这些蛋白质的功能具有从保护性生物膜环境中分解细菌和恢复抗生素活性的潜力。在这里，我们报道了基于半乳糖的树状大分子（Gal18）与LecA结合的NMR特征。此外，我们证明了Gal18分子在体外抑制铜绿假单胞菌生物膜形成的活性。
• End group functionalization of poly(ethylene glycol) with phenolphthalein: towards star-shaped polymers based on supramolecular interactions
  作者：Carolin Fleischmann、Hendrik Wöhlk、Helmut Ritter

  DOI：10.3762/bjoc.10.235

  日期：——

  The synthesis of a new phenolphthalein azide derivative, which can be easily utilized in polymer analogous reactions, is presented. The subsequent cycloaddition reaction with propargyl-functionalized methoxypoly(ethylene glycol) yielded polymers bearing phenolphthalein as the covalently attached end group. In presence of per-β-cyclodextrin-dipentaerythritol, the formation of stable inclusion complexes was observed, representing an interesting approach towards the formation of star shaped polymers. The decolorization of a basic polymer solution caused by the complexation was of great advantage since this behavior enabled following the complex formation by UV–vis spectroscopy and even the naked eye.

  提出了一种新的酚酞叠氮衍生物的合成方法，可以在聚合物类似反应中轻松使用。随后与丙炔功能化的甲氧基聚乙二醇进行环加成反应，得到带有酚酞作为共价连接端基团的聚合物。在存在per-β-环糊精-双戊四醇的情况下，观察到稳定的包含复合物的形成，代表了一种形成星形聚合物的有趣方法。由于这种复合物引起的碱性聚合物溶液褪色具有很大优势，因为这种行为使得可以通过紫外-可见光谱和甚至肉眼跟踪复合物的形成。