methyl (2S,4S)-4-azidopyrrolidine-2-carboxylate | 84520-69-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S,4S)-4-azidopyrrolidine-2-carboxylate
• 英文别名: cis-4-azido-L-proline methyl ester；4-(S)-azido-proline methyl ester；4-(S)-azido-(L)-proline methyl ester；methyl (2S,4S)-4-azidoprolinate
• CAS: 84520-69-4
• 化学式: C₆H₁₀N₄O₂
• 分子量: 170.171
• InChiKey: QJWIOUAZOWOZDS-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S,4S)-4-azidopyrrolidine-2-carboxylate 在 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 Boc-Pro-(4S)Azp-OH
  参考文献：
  名称：

  Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: towards antifreeze molecules

  摘要：

  用半乳糖偶联的氟化和非氟化脯氨酸寡聚体被合成并作为抗冻分子进行评估。

  DOI：

  10.1039/c8cc05588b
• 作为产物：
  描述：

  N-Boc-反式-4-羟基-L-脯氨酸甲酯 在 吡啶 、 sodium azide 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 methyl (2S,4S)-4-azidopyrrolidine-2-carboxylate
  参考文献：
  名称：

  Total synthesis and structure–activity relationships of new echinocandin-like antifungal cyclolipohexapeptides

  摘要：

  A series of new echinocandin-like cyclolipohexapeptides were designed and total synthesized via solution phase [3 + 3]-segment coupling strategy with an attempt to improve antifungal activity. The designed compounds showed potent antifungal activities with broad spectrum. In particular, 11 compounds (i.e. 28a-e, 28g, 28i-j, 29a, 29c and 29e) showed better in vitro antifungal activities against Candida albicans or Aspergillus fumigatus than caspofungin. Moreover, the synthesized compounds provided new SAR information for the echinocandins. The findings in this work suggested that the "left" tripeptide segment of cyclolipohexapeptide scaffold might be a hydrophilic structural motif, whereas the "right" lipopeptide segment was preferred as a hydrophobic core. The amino acid component of the cyclolipohexapeptide scaffold could significantly affect the SAR of the side chains. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.054

文献信息

• [EN] ANTIVIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013124335A1

  公开（公告）日：2013-08-29

  The present invention provides compounds of formula I, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

  本发明提供了式I的化合物，用于治疗丙型肝炎病毒（HCV）感染的组合物和方法。还公开了含有这些化合物的药物组合物以及在治疗HCV感染中使用这些化合物的方法。
• N-sulfonylindoline derivatives, their preparation and the pharmaceutical
  申请人：Elf Sanofi

  公开号：US05338755A1

  公开（公告）日：1994-08-16

  The invention relates to N-sulfonyl derivatives of formulae (I)" and (I)' ##STR1## and to pharmaceutical compositions in which they are present. The compounds have an affinity for the vasopressin and ocytocin receptors.

  这项发明涉及到式(I)和(I)'的N-磺酰基衍生物，以及它们存在的药物组合物。这些化合物具有对抗利尿素和催产素受体的亲和力。
• MacroEvoLution: A New Method for the Rapid Generation of Novel Scaffold-Diverse Macrocyclic Libraries
  作者：Jörn Saupe、Oliver Kunz、Lars Ole Haustedt、Sven Jakupovic、Christian Mang

  DOI：10.1002/chem.201703209

  日期：2017.9.4

  approach that gives reliable access to novel macrocyclic architectures. Classification of building blocks into specific pools ensures that scaffolds with orthogonally addressable functionalities are generated, which can easily be used for the generation of structurally diverse compound libraries. The method grants rapid access to novel scaffolds with scalable synthesis (multi gram scale) and the introduction

  大环化合物是结构类，对药物化学的未来挑战具有广阔的前景。然而，几乎没有灵活的方法可以快速生成结构多样的大环化合物集合。在这里，报告了一种有效的方法来生成新型的基于大环肽的支架。该过程在这里被称为“ MacroEvoLution”，是基于一种环化筛选方法的，该方法可以可靠地访问新颖的大环结构。将构建基块划分为特定的库可确保生成具有正交可寻址功能的支架，这些支架可轻松用于生成结构多样的化合物库。该方法可以快速访问具有可扩展合成（克级）的新型支架，并在后期引入更多的多样性。尽管已经开发出用于肽系统的方法，但是该方法可以容易地扩展为用于合成具有降低的肽特性的系统。
• [EN] PYRROLIDINE DERIVATIVES AS TRYPTASE INHIBITORS<br/>[FR] DERIVES DE PYRROLIDINE INHIBITEURS DE TRYPTASE
  申请人：ALTANA PHARMA AG

  公开号：WO2004012731A1

  公开（公告）日：2004-02-12

  Compounds of a certain formula 1 in which M, B1, B2, R2, K1 and K2 have the meanings indicated in the description are novel effective tryptase inhibitors.

  具有特定公式1的化合物，其中M、B1、B2、R2、K1和K2具有描述中指示的含义，是新颖有效的胰蛋白酶抑制剂。
• Mediators of hedgehog signaling pathways, compositions and uses related thereto
  申请人：——

  公开号：US20020165221A1

  公开（公告）日：2002-11-07

  The present invention makes available methods and reagents for inhibiting aberrant growth states resulting from hedgehog gain-of-function, ptc loss-of-function or smoothened gain-of-function comprising contacting the cell with a hedgehog antagonist, such as a small molecule, in a sufficient amount to aberrant growth state, e.g., to agonize a normal ptc pathway or antagonize smoothened or hedgehog activity.

  本发明提供了一种抑制由于hedgehog基因增强功能、ptc基因失效或smoothened基因增强功能引起的异常生长状态的方法和试剂，包括将细胞与hedgehog拮抗剂（例如小分子）接触，以足够的量来抑制异常生长状态，例如激活正常的ptc通路或拮抗smoothened或hedgehog活性。