5-azidopentyl trifluoromethanesulfonate | 170220-06-1

• 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
• 英文名称: 5-azidopentyl trifluoromethanesulfonate
• 英文别名: 5-azidopentyl triflate
• CAS: 170220-06-1
• 化学式: C₆H₁₀F₃N₃O₃S
• 分子量: 261.225
• InChiKey: XCAXBTYCVBIRBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-azidopentyl trifluoromethanesulfonate 在 sodium hydroxide 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 29.5h， 生成 2-(1H-indol-3-yl)ethyl 2,4-di-O-benzyl-3-deoxy-6-O-(5-aminopentyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Hirschmann, Ralph; Nicolaou; Pietranico, Sherrie, Journal of the American Chemical Society, 1993, vol. 115, # 26, p. 12550 - 12568

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴-1-戊醇 在 sodium azide 、 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.67h， 生成 5-azidopentyl trifluoromethanesulfonate
  参考文献：
  名称：

  Hirschmann, Ralph; Nicolaou; Pietranico, Sherrie, Journal of the American Chemical Society, 1993, vol. 115, # 26, p. 12550 - 12568

  摘要：

  DOI：

文献信息

• Effects of Heterocyclic Aromatic Substituents on Binding Affinities at Two Distinct Sites of Somatostatin Receptors. Correlation with the Electrostatic Potential of the Substituents
  作者：Vidya Prasad、Elizabeth T. Birzin、Cheryl T. McVaugh、Rachel D. van Rijn、Susan P. Rohrer、Gary Chicchi、Dennis J. Underwood、Edward R. Thornton、Amos B. Smith、Ralph Hirschmann

  DOI：10.1021/jm0205088

  日期：2003.5.1

  that the replacement of benzene or indole side chains by heterocyclic aromatic rings typified by pyridine and pyrazine not only enhances water solubility and hydrogen bonding capacity as expected, but can also profoundly diminish the ability of the pi-cloud of the aromatic substituent to interact with side chains of an aromatic binding pocket such as that for Trp(8) of SRIF-14. Conversely, these calculations

  在我们的持续计划中，研究生长抑素（SRIF-14）的基于葡萄糖的肽模拟物，我们试图改善糖苷的水溶性。这导致对SRIF受体上配体结合位点性质的见解。用吡啶基甲基或吡嗪-2-基甲基同源物代替葡糖苷（+）-2中的C4苄基取代基可增加水溶性，并增强对人SRIF亚型受体4（sst4）的亲和力。我们将此效应归因于氢键的形成。当与C2上的咪唑-4-基甲基结合时，C4上的吡啶-3-基甲基取代基生成（-）-19，这是迄今为止基于葡萄糖的拟肽对人SRIF受体的亲和力最高的（-）-19 （i）53 +/- 23 nM，在sst4时n = 6）。在异头碳上带有1-甲氧基取代基而不是吲哚侧链的葡糖苷的C4杂环同类物，也提供了有关Trp（8）结合口袋的信息。我们通过使用Spartan 3-21G（*）MO分析，将C4和Trp（8）结合口袋处的SAR与各种C4芳香族取代基的静电势计算相关联。这些计算提供了分子在受体结合
• Synthesis of Somatostatin Mimetics Based on the 1-Deoxymannojirimycin Scaffold
  作者：Sebastien G. Gouin、Paul V. Murphy

  DOI：10.1021/jo051454n

  日期：2005.10.1

  A novel synthesis of somatostatin mimetics based on the 1-deoxymannojirimycin (DMJ) scaffold has been developed. This involved development of a route suitable for the strategic grafting of pharmacophoric tryptophan and lysine side chains to the nitrogen atom of the piperidine ring and to the primary hydroxyl group of DMJ, respectively. The novel peptidomimetics were found to bind with higher affinity

  已开发出一种基于1-deoxymannojirimycin（DMJ）支架的生长抑素模拟物的新型合成方法。这涉及开发适合于将药效团的色氨酸和赖氨酸侧链分别战略性地接枝到哌啶环的氮原子和DMJ的伯羟基的途径。发现新型拟肽与sst4受体的结合比与sst5受体的结合具有更高的亲和力。
• Non-peptide peptidomimetics
  申请人：The Trustees of the University of Pennsylvania

  公开号：US06197963B1

  公开（公告）日：2001-03-06

  Compounds are provided which are crossreactive with peptides such as those which bind G-protein-linked receptors, together with preparative and therapeutic methods therefor. The compounds have the general structure: wherein at least one of R1, R2, R3, R4, or R5 comprises a functional group which is chemically similar to that found in the peptide of interest.

  提供了与结合G蛋白偶联受体的肽交叉反应的化合物，以及其制备和治疗方法。这些化合物具有以下一般结构：其中R1、R2、R3、R4或R5中至少有一个包含与感兴趣的肽中发现的化学相似的功能基团。
• Synthesis and Binding Affinities of Novel SRIF-Mimicking β-<scp>d</scp>-Glucosides Satisfying the Requirement for a π-Cloud at C1
  作者：Angie R. Angeles、Irina Neagu、Elizabeth T. Birzin、Edward R. Thornton、Amos B. Smith、Ralph Hirschmann

  DOI：10.1021/ol050119i

  日期：2005.3.1

  The synthesis of four bioactive analogues of the somatostatin (SRIF-14) mimetic, beta-D-glucoside (+)-2, in which the C1 indole side chain is replaced with indole surrogates, has been achieved. These congeners, possessing the naphthyl, benzothiophene, benzyl, and benzofuran substituents, were predicted to satisfy the electrostatic requirements of the tryptophan binding pocket of SRIF. Unlike the previously described C4 picolyl and pyrazinyl congeners, these ligands bind the hSST4 receptor.
• NON-PEPTIDE PEPTIDOMIMETICS
  申请人：THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA

  公开号：EP0728007A1

  公开（公告）日：1996-08-28