D-biotin-6-azido-n-hexylamide | 1349190-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: D-biotin-6-azido-n-hexylamide
• 英文别名: N-(5-azidopentyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide(biotin-(5-azido-pentyl)-amide)；biotine cadaverine azide；biotin-(5-azidopentyl)amide；5-(Biotinamido)pentylazide；5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-(5-azidopentyl)pentanamide
• CAS: 1349190-76-6
• 化学式: C₁₅H₂₆N₆O₂S
• 分子量: 354.476
• InChiKey: HGHJIFNOKMTXHY-OBJOEFQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  D-biotin-6-azido-n-hexylamide 、 在 copper(l) iodide 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以79%的产率得到
  参考文献：
  名称：

  Vitamin B₁₂ Derivatives for Orthogonal Functionalization

  摘要：

  The synthesis of vitamin B12 derivatives for selective orthogonal conjugation at both the Co center and 5'-OH is reported. Newly developed, reduction-free, direct alkynylation of vitamin B12 at the central cobalt ion proved to be versatile, with the formed acetylides, unlike other metalloorganic derivatives, showing remarkable heat and light stability, thus making them promising candidates as a drug carrier. Subsequently, high-yielding functionalization can be achieved via a sequence of selective [1,3] dipolar azide-alkyne cycloadditions (AACs) or carbamate formation followed by AAC.

  DOI：

  10.1021/jo501271g
• 作为产物：
  描述：

  5-(氨基维生素)戊胺 在 triflic azide 、 potassium carbonate 、 copper(II) sulfate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 D-biotin-6-azido-n-hexylamide
  参考文献：
  名称：

  [EN] BIOTIN-CONJUGATED N-ACETYL GLYCOL SPLIT HEPARIN
  [FR] HÉPARINE SÉPARÉE DE N-ACÉTYLE GLYCOL CONJUGUÉE À LA BIOTINE

  摘要：

  本发明涉及具有以下化学式（I）的生物素偶联的N-乙酰甘露醇分裂肝素分子，其中取代基的含义在说明中披露。本发明还涉及用作药物的这种化合物，特别是用于治疗与肝素酶活性相关的疾病和紊乱，并且涉及包含相同化合物的药物组合物。

  公开号：

  WO2018188990A1

文献信息

• Identification of a Selective, Activity-Based Probe for Glyceraldehyde 3-Phosphate Dehydrogenases
  作者：Farnusch Kaschani、Jérôme Clerc、Daniel Krahn、David Bier、Tram Ngoc Hong、Christian Ottmann、Sherry Niessen、Tom Colby、Renier A. L. van der Hoorn、Markus Kaiser

  DOI：10.1002/anie.201107276

  日期：2012.5.21

  The natural‐product‐like structural complexity of a bicyclic hydantoin was exploited to generate the novel, highly specific activity‐based profiling probe (ABPP) Mrl‐Rh (Rh=rhodamine; see picture) for glyceraldehyde 3‐phosphate dehydrogenases. This probe can be used to investigate activity changes of this enzyme class during plant–pathogen interactions.

  特异：利用双环乙内酰脲的天然产物状结构复杂性，生成了针对甘油醛3-磷酸脱氢酶的新型，高度特异性的基于活性的轮廓分析探针（ABPP）Mr1-Rh（Rh =罗丹明;见图）。该探针可用于研究植物与病原体相互作用期间该酶类别的活性变化。
• The Cu(<scp>i</scp>)-catalysed Huisgen 1,3-dipolar cycloaddition route to (bio-)organic functionalisation of polyoxovanadates
  作者：Oliver Linnenberg、Aleksandar Kondinski、Cornelia Stöcker、Kirill Yu. Monakhov

  DOI：10.1039/c7dt03376a

  日期：——

  We elaborated a synthetic protocol that provides convenient access to a “click”-directed covalent conjugation between ⁵¹V-NMR detectable, redox-active polyoxo(alkoxo)vanadate and (bio-)organoazides. The compounds can potentially be used in bioelectronics, biocatalysis and biosensorics.

  我们制定了一个合成方案，可以方便地实现⁵¹V-NMR可检测的、具有氧化还原活性的聚氧(烷氧)钒酸盐与(生物-)有机叠氮化合物之间的“点击”定向共价结合。这些化合物有望在生物电子学、生物催化和生物传感领域中使用。
• ZANAMIVIR PHOSPHONATE CONGENERS WITH ANTI-INFLUENZA ACTIVITY AND DETERMINING OSELTAMIVIR SUSCEPTIBILITY OF INFLUENZA VIRUSES
  申请人：Wong Chi-Huey

  公开号：US20130225532A1

  公开（公告）日：2013-08-29

  Methods and compositions for detection of drug resistant pathogens and treatment against infections thereof are provided. Methods for detection of oseltamivir-resistant influenza viruses by competitive binding assays utilizing non-oseltamivir influenza virus neuraminidase inhibitors and oseltamivir carboxylate are provided. Influenza virus neuraminidase inhibitors coupled to sensors and useful for employment in the methods of the invention are disclosed. Novel phosphonate compounds active as neuraminidase inhibitors against wild-type and oseltamivir-resistant influenza strains of H1N1, H5N1 and H3N2 viruses are disclosed. An enantioselective synthetic route to preparation of these phosphonate compounds via sialic acid is provided.

  本发明提供了检测耐药病原体和治疗感染的方法和组合物。本发明提供了利用非奥司他韦流感病毒神经氨酸酶抑制剂和奥司他韦羧酸盐进行竞争结合测定的检测奥司他韦耐药性流感病毒的方法。本发明还揭示了与传感器耦合并在本发明方法中使用的流感病毒神经氨酸酶抑制剂。本发明还揭示了对H1N1、H5N1和H3N2病毒的野生型和奥司他韦耐药株具有神经氨酸酶抑制剂活性的新型膦酸酯化合物。本发明还提供了通过唾液酸的对映选择性合成途径制备这些膦酸酯化合物的方法。
• ZANAMIVIR PHOSPHONATE CONGENERS WITH ANTI-INFLUENZA ACTIVITY AND DETERMINING OSELTAMIVIR SUSCEPTIBILITY OF INFLUENZA VIRUSES
  申请人：Academia Sinica

  公开号：EP2975409A1

  公开（公告）日：2016-01-20

  Methods and compositions for detection of drug resistant pathogens and treatment against infections thereof are provided. Methods for detection of oseltamivir-resistant influenza viruses by competitive binding assays utilizing non-oseltamivir influenza virus neuraminidase inhibitors and oseltamivir carboxylate are provided. Influenza virus neuraminidase inhibitors coupled to sensors and useful for employment in the methods of the invention are disclosed. Novel phosphonate compounds active as neuraminidase inhibitors against wild-type and oseltamivir-resistant influenza strains of H1N1, H5N1 and H3N2 viruses are disclosed. An enantioselective synthetic route to preparation of these phosphonate compounds via sialic acid is provided.

  提供了检测耐药病原体和治疗其感染的方法和组合物。本发明提供了通过利用非奥司他韦流感病毒神经氨酸酶抑制剂和奥司他韦羧酸盐的竞争性结合测定来检测抗奥司他韦流感病毒的方法。本发明公开了与传感器结合并可用于本发明方法的流感病毒神经氨酸酶抑制剂。本发明公开了新型膦酸盐化合物，作为神经氨酸酶抑制剂对野生型和抗奥司他韦的 H1N1、H5N1 和 H3N2 流感病毒株具有活性。本发明提供了通过硅烷酸制备这些膦酸盐化合物的对映体选择性合成路线。
• Novel N-acetyl-Glycol-split heparin biotin-conjugates endowed with anti-heparanase activity
  作者：Emiliano Esposito、Israel Vlodavsky、Uri Barash、Giuseppe Roscilli、Ferdinando M. Milazzo、Giuseppe Giannini、Annamaria Naggi

  DOI：10.1016/j.ejmech.2019.111831

  日期：2020.1

  Heparanase is regarded as a promising target for anticancer drugs and Ronepastat is one of the most promising heparanase inhibitors insert in clinical study for Multiple Myeloma Therapy. To improve its pharmacokinetic/pharmacodynamic profile, as well to have an antidote able to neutralize its activity in case of over dosages or intolerance, a new class of its derivatives was obtained inserting non-carbohydrate moieties of different length between the polysaccharide chain and biotin or its derivatives. In vitro these novel derivatives maintain the anti-heparanase activity without induced toxicity. The newly synthesized compounds retained the ability to attenuate the growth of CAG myeloma tumors in mice with potency similar, or in one case even higher than that of the reference compound Roneparstat as well as inhibited metastatic dissemination (lung colonization) of murine B16-F10 melanoma cells in vivo. (C) 2019 Elsevier Masson SAS. All rights reserved.