(-)-(2S)-3-azidopropane-1,2-diol | 85820-84-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (-)-(2S)-3-azidopropane-1,2-diol
• 英文别名: (2S)-3-azido-1,2-propanediol；(S)-3-azido-1,2-propane diol；(S)-3-azido-1,2-propanediol；(S)-3-azidopropane-1,2-diol；(S)-3-Azido-1,2-propandiol；3-azido-1,2(S)-propanediol；(2S)-3-azidopropane-1,2-diol
• CAS: 85820-84-4
• 化学式: C₃H₇N₃O₂
• 分子量: 117.107
• InChiKey: HTTNJQAFJLVWCN-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  炔雌醇 、 (-)-(2S)-3-azidopropane-1,2-diol 在 copper(II) sulfate sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 以94%的产率得到(2S)-17-[1-(2,3-dihydroxypropyl)-1H-[1,2,3]-triazol-4-yl]estradiol
  参考文献：
  名称：

  [EN] COPPER-CATALYSED LIGATION OF AZIDES AND ACETYLENES
  [FR] LIGATION D'AZIDES ET D'ACETYLENES CATALYSEE PAR LE CUIVRE

  摘要：

  利用金属催化的点击化学连接过程，将叠氮化物和末端乙炔结合，形成三唑。在许多情况下，该反应序列特异地连接叠氮化物和末端乙炔，仅生成1,4-二取代[1,2,3]-三唑。

  公开号：

  WO2003101972A1
• 作为产物：
  描述：

  (R)-(-)-对甲基苯磺酸-2,2-二甲基-1,3-二氧戊环基-4-甲酯 在 sodium azide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到(-)-(2S)-3-azidopropane-1,2-diol
  参考文献：
  名称：

  Ziegler, Thomas; Straub, Alexander; Effenberger, Franz, Angewandte Chemie, 1988, vol. 100, # 5, p. 737 - 738

  摘要：

  DOI：

文献信息

• Curcumin derivatives with improved physicochemical properties and nanoliposomes surface-decorated with the derivatives with very high affinity for amyloid-beta1-42 peptide
  申请人：Niaraki, Anna

  公开号：EP2436673A1

  公开（公告）日：2012-04-04

  Amyloid β (Aβ) aggregates are considered as possible targets for therapy and/or diagnosis of Alzheimer disease (AD). It has been previously shown that curcumin targets Aβ plaques and interferes with their formation, suggesting a potential role for prevention or treatment of AD. In the present invention, curcumin-derivatives with improved physicochemical properties were synthesized and a "click chemistry" as well as a conventional liposome preparation method, were used to generate nanoliposomes decorated with the curcumin derivatives. These derivatives were designed to maintain the planar structure required for interaction with Aβ, as directly confirmed by Surface Plasmon Resonance experiments. Surface Plasmon Resonance experiments, measuring the binding of flowing liposomes to immobilized Aβ1-42, indicated that the liposomes exposing curcumin derivatives have extremely high affinity for Aβ1-42 fibrils (1-5 nM), likely because of the occurrence of multivalent interactions. The present invention describes the synthesis of the curcumin derivatives and the preparation and characterization of new nanoliposomes with a very high affinity for Aβ1-42 fibrils, to be exploited as vectors for the targeted delivery of new diagnostic and therapeutic molecules for AD.

  淀粉样蛋白β（Aβ）聚集物被认为是治疗和/或诊断阿尔茨海默病（AD）的可能靶点。先前已经显示姜黄素靶向Aβ斑块并干扰其形成，暗示了其在预防或治疗AD中的潜在作用。在本发明中，合成了具有改进的物理化学性质的姜黄素衍生物，并使用“点击化学”以及传统的脂质体制备方法，生成了装饰有姜黄素衍生物的纳米脂质体。这些衍生物被设计为保持与Aβ相互作用所需的平面结构，直接通过表面等离子共振实验证实。通过测量流动脂质体与固定的Aβ1-42的结合，表面等离子共振实验证明，暴露姜黄素衍生物的脂质体对Aβ1-42纤维具有极高的亲和力（1-5 nM），可能是由于多价相互作用的发生。本发明描述了姜黄素衍生物的合成以及具有极高亲和力的新型纳米脂质体的制备和表征，可作为用于靶向传递新的AD诊断和治疗分子的载体。
• A Clickable and Photocleavable Lipid Analogue for Cell Membrane Delivery and Release
  作者：Shahrina Alam、Daiane S. Alves、Stuart A. Whitehead、Andrew M. Bayer、Christopher D. McNitt、Vladimir V. Popik、Francisco N. Barrera、Michael D. Best

  DOI：10.1021/acs.bioconjchem.5b00044

  日期：2015.6.17

  For drug delivery purposes, the ability to conveniently attach a targeting moiety that will deliver drugs to cells and then enable controlled release of the active molecule after localization is desirable. Toward this end, we designed and synthesized clickable and photocleavable lipid analogue 1 to maximize the efficiency of bioconjugation and triggered release. This compound contains a dibenzocyclooctyne group for bioorthogonal derivatization linked via a photocleavable 2-nitrobenzyl moiety at the headgroup of a synthetic lipid backbone for targeting to cell membranes. To assess delivery and release using this system, we report fluorescence-based assays for liposomal modification and photocleavage in solution as well as through surface immobilization to demonstrate successful liposome functionalization and photoinduced release. In addition, fluorophore delivery to and release from live cells was confirmed and characterized using fluorescence microscopy and flow cytometry analysis in which 1 was delivered to cells, derivatized, and photocleaved. Finally, drug delivery studies were performed using an azide-tagged analogue of camptothecin, a potent anticancer drug that is challenging to deliver due to poor solubility. In this case, the ester attachment of the azide tag acted as a caging group for release by intracellular esterases rather than through photocleavage. This resulted in a dose-dependent response in the presence of liposomes containing delivery agent 1, confirming the ability of this compound to stimulate delivery to the cytoplasm of cells.

  为了实现药物递送的目的，能够方便地附加一个靶向部分，将药物递送至细胞，并在定位后实现活性分子的可控释放，这是可取的。为此，我们设计并合成了可点击且光裂解的脂质类似物1，以最大限度地提高生物共轭和触发释放的效率。该化合物包含一个通过光裂解的2-硝基苄基部分连接的二苯并环辛炔基团，位于合成脂质骨架的头部，用于靶向细胞膜。为了评估该系统的递送和释放，我们报道了基于荧光的脂质体修饰和溶液中以及通过表面固定化的光裂解实验，以证明成功实现脂质体功能化和光诱导释放的证据。此外，通过荧光显微镜和流式细胞术分析确认并表征了荧光团向活细胞的递送和释放，其中1被递送至细胞、衍生化并光裂解。最后，使用了一种带有叠氮标记的喜树碱类似物进行药物递送研究，喜树碱是一种具有强抗癌活性的药物，但由于其溶解性差而难以递送。在这种情况下，叠氮标签的酯键连接起到了笼蔽基团的作用，通过细胞内酯酶的释放而不是光裂解。结果显示，在含有递送剂1的脂质体存在下，剂量依赖性响应得到了确认，证实了该化合物刺激细胞质内部递送的能力。
• Synthesis of β-Hydroxyphosphonate and 1,2-Dihydroxy Acyclic Nucleoside Analogs via 1,3-Dipolar Cycloaddition Strategy
  作者：M. Ganesan、K. M. Muraleedharan

  DOI：10.1080/15257771003597709

  日期：2010.2.26

  A convenient synthetic approach toward nucleoside analogs where β-hydroxyphosphonate- or 1,2-dihydroxy units are connected to the nucleic acid base through a triazole spacer is discussed.

  讨论了一种方便的核苷类似物合成方法，其中 β-羟基膦酸酯或 1,2-二羟基单元通过三唑间隔物连接到核酸碱基。
• Synthesis of Phosphonoglycine Backbone Units for the Development of Phosphono Peptide Nucleic Acids
  作者：Bogdan Doboszewski、Elisabetta Groaz、Piet Herdewijn

  DOI：10.1002/ejoc.201300523

  日期：2013.8

  phosphono-modified backbone mimics based on achiral and chiral N-(dihydroxypropyl)glycine units were obtained by sequential addition of phosphonate and nucleobase moieties to suitably protected dihydroxypropylamines. Simple synthetic strategies enabled the preparation of various target derivatives that will be useful as building blocks for the preparation of new synthetic polymers containing a phosphonate

  一系列基于非手性和手性 N-（二羟丙基）甘氨酸单元的膦酰基修饰的骨架模拟物通过将膦酸酯和核碱基部分顺序添加到适当保护的二羟丙胺中获得。简单的合成策略能够制备各种目标衍生物，这些衍生物可用作构建新合成聚合物的构建单元，这些聚合物包含一个膦酸酯核苷酸间键代替标准磷酸二酯键。
• Synthesis and Biological Evaluation of Novel Gramicidin S Analogues
  作者：Adriaan Willem Tuin、Dimitrios Konstantinos Palachanis、Annelies Buizert、Gijsbert Marnix Grotenbreg、Emile Spalburg、Albert J. de Neeling、Roos H. Mars-Groenendijk、Daan Noort、Gijsbert A. van der Marel、Herman S. Overkleeft、Mark Overhand

  DOI：10.1002/ejoc.200900460

  日期：2009.9

  The synthesis of three new analogues of the cyclic cationic antimicrobial peptide Gramicidin S is described. These derivatives contain a modified turn region in which the DPhe-Pro motif has been replaced by a constrained furanoid sugar amino acid or a flexible linear aminoethoxy acetic acid moiety. Structural analysis revealed conformational changes in the modified turn region compared to GS. The biological

  描述了环状阳离子抗菌肽短杆菌肽 S 的三种新类似物的合成。这些衍生物含有修饰的转角区，其中 DPhe-Pro 基序已被限制性呋喃糖氨基酸或灵活的线性氨基乙氧基乙酸部分取代。结构分析揭示了与 GS 相比，修饰的转角区域的构象变化。然而，这些化合物的生物学特征类似于短杆菌肽 S 和先前描述的类似物。© 2009 Wiley-VCH Verlag GmbH & Co. KGaA，魏因海姆。