4-氨基-3-[[4-[[4-[[2-氨基-4-[[2-(二乙胺基)乙基]氨基]苯基]偶氮]苯基]氨基]-3-磺酸根苯基]偶氮]-5-羟基-6-(苯偶氮基)萘-2,7-二磺化三钠 | 363172-09-2

• 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
• 中文名称: 4-氨基-3-[[4-[[4-[[2-氨基-4-[[2-(二乙胺基)乙基]氨基]苯基]偶氮]苯基]氨基]-3-磺酸根苯基]偶氮]-5-羟基-6-(苯偶氮基)萘-2,7-二磺化三钠
• 英文名称: (3R,4R,5S)-3-amino-4,5-dimethyldihydrofuran-2(3H)-one
• 英文别名: (2S,3R,4R)-4-Hydroxy-isoleucin-lacton；(3R,4R,5S)-3-amino-4,5-dimethyloxolan-2-one
• CAS: 363172-09-2
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: DXLUNIWVHZZSPK-VAYJURFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氨基-3-[[4-[[4-[[2-氨基-4-[[2-(二乙胺基)乙基]氨基]苯基]偶氮]苯基]氨基]-3-磺酸根苯基]偶氮]-5-羟基-6-(苯偶氮基)萘-2,7-二磺化三钠 、 (Z,Z)-9,12-十八烷二烯酸二聚物 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以94%的产率得到(9Z,12Z)-N-((3R,4R,5S)-4,5-dimethyl-2-oxotetrahydrofuran-3-yl)octadeca-9,12-dienamide
  参考文献：
  名称：

  N55的全合成和绝对结构，GLP-1信号的正调节剂

  摘要：

  胰高血糖素样肽-1 (GLP-1) 信号传导是 2 型糖尿病 (T2DM) 的既定治疗靶点。我们开发了N55的 7 步合成，这是从葫芦巴 ( Trigonella foenum-graecum ) 种子中分离的 GLP-1 信号的正调节剂，总产率为 29%，我们确定N55的绝对结构为N -((3 R ,4 R ,5 S )-4,5-二甲基-2-氧代四氢呋喃-3-基)亚油酰胺。

  DOI：

  10.1039/d0ob01722a
• 作为产物：
  描述：

  (3R,4R,5S)-3-(dibenzylamino)-4,5-dimethyldihydrofuran-2(3H)-one 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以99%的产率得到4-氨基-3-[[4-[[4-[[2-氨基-4-[[2-(二乙胺基)乙基]氨基]苯基]偶氮]苯基]氨基]-3-磺酸根苯基]偶氮]-5-羟基-6-(苯偶氮基)萘-2,7-二磺化三钠
  参考文献：
  名称：

  N55的全合成和绝对结构，GLP-1信号的正调节剂

  摘要：

  胰高血糖素样肽-1 (GLP-1) 信号传导是 2 型糖尿病 (T2DM) 的既定治疗靶点。我们开发了N55的 7 步合成，这是从葫芦巴 ( Trigonella foenum-graecum ) 种子中分离的 GLP-1 信号的正调节剂，总产率为 29%，我们确定N55的绝对结构为N -((3 R ,4 R ,5 S )-4,5-二甲基-2-氧代四氢呋喃-3-基)亚油酰胺。

  DOI：

  10.1039/d0ob01722a

文献信息

• Method for preparing 4-hydroxyisoleucine diastereoisomers and enantiomers and derivatives thereof
  申请人：Mioskowski Charles

  公开号：US20060205817A1

  公开（公告）日：2006-09-14

  The invention concerns a method for preparing 4-hydroxyisoleucine diastereoisomers and enantiomers and derivatives thereof of general formula (I), characterized in that it consists in reducing an isoxazole derivative of formula (II) in conditions directly resulting in the derivatives of formula (I), or in obtaining at least a lactone of structure (III) in racemic form(s), or a enantiomerically enriched mixture, followed by opening, in basic conditions, in an aprotic or protic solvent, the desired lactone(s) and, optionally, separating the desired form. The invention is useful for preparing in particular (2S, 3R, 4S)-4-hydroxyisoleucine

  该发明涉及一种制备4-羟基异亮氨酸对映体和差向异构体及其衍生物的方法，其一般式为(I)，其特征在于它包括在直接导致式(I)衍生物的条件下还原一种异噁唑烷衍生物的步骤，或者在获得至少一种外消旋形式的结构为(III)的内酯，或者在手性富集混合物中，然后在碱性条件下，在无极性或极性溶剂中开环所需的内酯，并且可选地分离所需的形式。该发明可用于特别制备(2S, 3R, 4S)-4-羟基异亮氨酸。
• Method for preparing (2S, 3R, 4S) -4-hydroxyisoleucine and analogues thereof
  申请人：Ouazzani Jamal

  公开号：US20050079587A1

  公开（公告）日：2005-04-14

  The invention concerns a method for preparing a-amino acids of general formula (2S-1) wherein: the group R1 represents a hydrogen atom, a group protecting the amino group or a group of formula —COOR2 wherein the group R2 represents a C1-C6 alkyl group, an aryl or aralkyl group. The invention also concerns a-amino acids of general formula (2S-1) wherein the group R1 represents a group protecting the amino group or a group of formula —COOR2 wherein the group R2 represents a C1-C6 alkyl group, an aryl or aralkyl group and their use as medicine.

  该发明涉及一种制备通式（2S-1）的α-氨基酸的方法，其中：基团R1代表氢原子、保护氨基的基团或者通式—COOR2的基团，其中基团R2代表C1-C6烷基、芳基或芳基烷基。该发明还涉及通式（2S-1）的α-氨基酸，其中基团R1代表保护氨基的基团或者通式—COOR2的基团，其中基团R2代表C1-C6烷基、芳基或芳基烷基，并且它们的用途为药物。
• Method for preparing (2s,3r,4s)-4-hydroxyisoleucine and analogues thereof
  申请人：——

  公开号：US20030219880A1

  公开（公告）日：2003-11-27

  The invention concerns a method for preparing a-amino acids of general formula (2S-1) wherein: the group R1 represents a hydrogen atom, a group protecting the amino group or a group of formula —COOR2 wherein the group R2 represents a C1-C6 alkyl group, an aryl or aralkyl group. The invention also concerns a-amino acids of general formula (2S-1) wherein the group R1 represents a group protecting the amino group or a group of formula —COOR2 wherein the group R2 represents a C1-C6 alkyl group, an aryl or aralkyl group and their use as medicine.

  本发明涉及一种制备通式为(2S-1)的α-氨基酸的方法，其中：基团R1表示氢原子、保护氨基的基团或通式为—COOR2的基团，其中基团R2表示C1-C6烷基、芳基或芳基烷基。本发明还涉及通式为(2S-1)的α-氨基酸，其中基团R1表示保护氨基的基团或通式为—COOR2的基团，其中基团R2表示C1-C6烷基、芳基或芳基烷基，并且它们的用途是作为药物。
• Isolation of Positive Modulator of Glucagon-like Peptide-1 Signaling from Trigonella foenum-graecum (Fenugreek) Seed
  作者：Klim King、Nai-Pin Lin、Yu-Hong Cheng、Gao-Hui Chen、Rong-Jie Chein

  DOI：10.1074/jbc.m115.672097

  日期：2015.10

  The glucagon-like peptide-1 receptor (GLP-1R) is expressed in many tissues and has been implicated in diverse physiological functions, such as energy homeostasis and cognition. GLP-1 analogs are approved for treatment of type 2 diabetes and are undergoing clinical trials for other disorders, including neurodegenerative diseases. GLP-1 analog therapies maintain chronically high plasma levels of the analog and can lead to loss of spatiotemporal control of GLP-1R activation. To avoid adverse effects associated with current therapies, we characterized positive modulators of GLP-1R signaling. We screened extracts from edible plants using an intracellular cAMP biosensor and GLP-1R endocytosis assays. Ethanol extracts from fenugreek seeds enhanced GLP-1 signaling. These seeds have previously been found to reduce glucose and glycated hemoglobin levels in humans. An active compound (N55) with a new N-linoleoyl-2-amino-gamma-butyrolactone structure was purified from fenugreek seeds. N55 promoted GLP-1-dependent cAMP production and GLP-1R endocytosis in a dose-dependent and saturable manner. N55 specifically enhanced GLP-1 potency more than 40-fold, but not that of exendin 4, to stimulate cAMP production. In contrast to the current allosteric modulators that bind to GLP-1R, N55 binds to GLP-1 peptide and facilitates trypsinmediated GLP-1 inactivation. These findings identify a new class of modulators of GLP-1R signaling and suggest that GLP-1 might be a viable target for drug discovery. Our results also highlight a feasible approach for screening bioactive activity of plant extracts.
• US7420087B2
  申请人：——

  公开号：US7420087B2

  公开（公告）日：2008-09-02