(2R,3R,4S)-4-azido-3-(benzyloxy)tetrahydrofuran-2-carbaldehyde | 1017236-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,4S)-4-azido-3-(benzyloxy)tetrahydrofuran-2-carbaldehyde
• 英文别名: (2R,3R,4S)-4-azido-3-phenylmethoxyoxolane-2-carbaldehyde
• CAS: 1017236-03-1
• 化学式: C₁₂H₁₃N₃O₃
• 分子量: 247.254
• InChiKey: ICOURFPNQXEZQW-SDDRHHMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-4-azido-3-(benzyloxy)tetrahydrofuran-2-carbaldehyde 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以70 mg的产率得到(2R,3R,4S)-4-叠氮基-3-(苄氧基)四氢呋喃-2-羧酸
  参考文献：
  名称：

  从糖类中一般高效地立体选择性合成γ-叠氮基-四氢呋喃羧酸

  摘要：

  对映体纯γ叠氮基四氢呋喃羧酸单体（的有效，直接和一般合成5 - 8）从可商购的烯糖，合适的与易感染的构象来设计肽模拟物的低聚物进行说明。的单晶X射线研究8 表明，该化合物在正交空间群结晶。晶体堆积表明存在弱的分子间C–H⋯O和脂族C–H⋯π相互作用。

  DOI：

  10.1016/j.tet.2007.12.032
• 作为产物：
  描述：

  (2R,3R,4S)-4-azido-3-(benzyloxy)-2-(dimethoxymethyl)tetrahydrofuran 在 水 、 三氟乙酸 作用下， 反应 2.0h， 以95%的产率得到(2R,3R,4S)-4-azido-3-(benzyloxy)tetrahydrofuran-2-carbaldehyde
  参考文献：
  名称：

  用于折叠聚体和肽纳米管的环状γ-氨基酸的合成

  摘要：

  环状γ-氨基酸是肽和折叠体化学中非常受关注的分子构建块，因为它们允许制备自然界中未发现的新结构。在本文中，我们描述了在氨基和羧酸基团之间具有顺式关系的环状 γ-氨基酸的合成。在大多数情况下，这种排列会导致生成的肽采用扁平构象，这使得它们适用于采用 β-折叠型结构的折叠体的设计。

  DOI：

  10.1002/ejoc.201201565

文献信息

• α,γ-Cyclic peptide ensembles with a hydroxylated cavity
  作者：César Reiriz、Manuel Amorín、Rebeca García-Fandiño、Luis Castedo、Juan R. Granja

  DOI：10.1039/b911247m

  日期：——

  Here we describe a self-assembling α,γ-cyclic tetrapeptide that contains the 4-amino-3-hydroxytetrahydrofuran-2-carboxylic acid, in which the hydroxy group is pointing towards the inner cavity of the resulting dimers.

  在这里，我们描述了一种含有 4-氨基-3-羟基四氢呋喃-2-羧酸的自组装δ,δ-环四肽，其中的羟基指向所得二聚体的内腔。
• BIHETEROARYL COMPOUNDS AND USES THEREOF
  申请人：Genentech, Inc.

  公开号：US20160052940A1

  公开（公告）日：2016-02-25

  The present invention provides for compounds of Formula I-I and embodiments and salts thereof for the treatment of diseases (e.g., neurodegenerative diseases). R 1 , R 2 , R 3 , X 1 , X 2 , A and Cy variable in Formula I-I all have the meaning as defined herein.

  本发明提供了I-I式化合物及其衍生物和盐，用于治疗疾病（例如神经退行性疾病）。公式I-I中的R1、R2、R3、X1、X2、A和Cy变量均具有本文所定义的含义。
• Biheteroaryl compounds and uses thereof
  申请人：Genentech, Inc.

  公开号：US10010549B2

  公开（公告）日：2018-07-03

  The present invention provides for compounds of Formula I-I and embodiments and salts thereof for the treatment of diseases (e.g., neurodegenerative diseases). R1, R2, R3, X1, X2, A and Cy variable in Formula I-I all have the meaning as defined herein.

  本发明提供了用于治疗疾病（如神经退行性疾病）的式-I-I化合物及其实施方案和盐。式-I-I中的R1、R2、R3、X1、X2、A和Cy变量均具有本文所定义的含义。
• Discovery of novel jaspine B analogues as autophagy inducer
  作者：En Zhang、Shang Wang、Li-Li Li、Yong-Gang Hua、Jing-Fei Yue、Jin-Feng Li、Cheng-Yun Jin

  DOI：10.1016/j.bmcl.2017.12.011

  日期：2018.2

  A series of 2-alkylaminomethyl jaspine B analogues were synthesized and evaluated for their cytotoxic effects on human lung adenocarcinoma, breast cancer, and prostate cancer cell lines and a mouse melanoma cell line. Most of the compounds exhibited moderate to good activity against the cancer cell lines. Compound 7f showed the best overall cytotoxicity on PC-3 cells (IC50 = 0.85 mu M). Further mechanistic studies revealed that compound 7f induced marked changes in PC-3 cell morphology, disrupted the mitochondrial membrane potential, and increased expression of the autophagy proteins beclin-1, LC3, and P62. (C) 2017 Elsevier Ltd. All rights reserved.
• Synthesis and preliminary biological evaluation of 1,2,3-triazole-Jaspine B hybrids as potential cytotoxic agents
  作者：Jin-Mei Xu、En Zhang、Xiao-Jing Shi、Yan-Chao Wang、Bin Yu、Wei-Wei Jiao、Ya-Zhuo Guo、Hong-Min Liu

  DOI：10.1016/j.ejmech.2014.03.022

  日期：2014.6

  Two series of more available novel 1,2,3-triazole-Jaspine B hybrids were efficiently synthesized employing click chemistry approach and evaluated for their cytotoxic activities against three human cancer cell lines (EC-9706, MGC-803 and MCF-7). Among them, compound 14h showed excellent inhibition against MCF-7 (IC50 = 1.93 μM) and was more potent than 5-Fu and Jaspine B against all three cancer cell lines. Further investigation of apoptosis assay and cell cycle analysis demonstrated that compound 14h caused cellular early and late apoptosis and arrested the cell cycle at G2/M phase in a concentration- and time-independent manner. This was the first report about the synthesis and in vitro cytotoxic evaluation of 1,2,3-triazole-Jaspine B hybrids.