methyl N-(3-hydroxypropyl)glycinate | 174561-66-1

• 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 N-(3-hydroxypropyl)glycinate
• 英文别名: Methyl 2-(3-hydroxypropylamino)acetate
• CAS: 174561-66-1
• 化学式: C₆H₁₃NO₃
• mdl: MFCD12179270
• 分子量: 147.174
• InChiKey: ZDDZWRMLJXLCLS-UHFFFAOYSA-N

物化性质

• 沸点：
  241.3±25.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl N-(3-hydroxypropyl)glycinate 在 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 生成
  参考文献：
  名称：

  氢键替代稳定的水溶性3 10螺旋，其来自含有编码α-氨基酸的无序五肽

  摘要：

  更换假想I + 3→1肽H-键无序五肽，即缺乏任何helicogenicÇ α -tetrasubstituted残基，具有丙基接头和氨甲酰化的N末端氮约束它在难以捉摸3 10具有高螺旋结构通过NMR和CD分析证实了在温度和pH值变化的条件下的螺旋度和稳定性。

  DOI：

  10.1016/j.tetlet.2018.05.029
• 作为产物：
  描述：

  在 potassium carbonate 、 苯硫酚 作用下， 以 乙腈 为溶剂， 生成 methyl N-(3-hydroxypropyl)glycinate
  参考文献：
  名称：

  氢键替代稳定的水溶性3 10螺旋，其来自含有编码α-氨基酸的无序五肽

  摘要：

  更换假想I + 3→1肽H-键无序五肽，即缺乏任何helicogenicÇ α -tetrasubstituted残基，具有丙基接头和氨甲酰化的N末端氮约束它在难以捉摸3 10具有高螺旋结构通过NMR和CD分析证实了在温度和pH值变化的条件下的螺旋度和稳定性。

  DOI：

  10.1016/j.tetlet.2018.05.029

文献信息

• Trimodular Solution‐Phase Protocol for Rapid Large‐Scale Synthesis of Hydrogen Bond Surrogate‐Constrained α‐Helicomimics
  作者：Sunit Pal、Erode N. Prabhakaran

  DOI：10.1002/ejoc.202001359

  日期：2021.3.19

  cost‐effective, high‐yielding, rapid trimodular solution‐phase method has been demonstrated to synthesize the hydrogen bond surrogate (HBS) constrained single α‐helical turn and C‐terminal extended helices. The HBS‐constrained α‐helicomimic is divided into three modules and each of them was synthesized in 100 mmol scale followed by connecting them to adopt the α‐helicomimic.

  已经证明了一种经济高效，高产量的快速三模溶液相方法可以合成氢键替代物（HBS）约束的单个α螺旋圈和C端扩展螺旋。将受HBS约束的α螺旋体分为三个模块，每个模块以100 mmol的比例合成，然后将它们连接起来以采用α螺旋体。
• Combination of click chemistry and sulfonamides to develop three-armed triazole compounds
  作者：Pierangelo Fabbrizzi、Francesca Bianchini、Gloria Menchi、Silvia Raspanti、Antonio Guarna、Andrea Trabocchi

  DOI：10.1016/j.tet.2014.06.125

  日期：2014.9

  Fragment-based drug discovery is a valuable tool in hit identification, as well as the combination of different small fragments showing a minimal binding activity against biological receptors or enzymes to give merged hits. A high number of fragments on the same scaffold improve the probability to find a candidate showing single- or multi-target affinities. A rapid and versatile approach for synthesizing libraries of densely fragment-functionalized scaffolds is reported. Many fragments were assembled in few steps around a triazole ring starting from amino alcohols and other readily available building blocks. A binding assay against integrin alpha(v)beta(3) was used as a test-bed in order to demonstrate the potential of such an approach in hit discovery strategies. (C) 2014 Elsevier Ltd. All rights reserved.
• Design, synthesis and evaluation of novel oxazaphosphorine prodrugs of 9-(2-phosphonomethoxyethyl)adenine (PMEA, adefovir) as potent HBV inhibitors
  作者：Peng Lu、Jiangxia Liu、Yuya Wang、Xiaoyan Chen、Yushe Yang、Ruyun Ji

  DOI：10.1016/j.bmcl.2009.10.072

  日期：2009.12

  A series of novel oxazaphosphorine prodrugs of 9-(2-phosphonomethoxyethyl)adenine (PMEA, adefovir) were synthesized and their anti-hepatitis B virus (HBV) activity was evaluated in HepG2 2.2.15 cells, with adefovir dipivoxil as a reference drug. In the cell assays, compounds 7b and 7d exhibited anti-HBV activity comparable to that of adefovir dipivoxil, while compound 7c, with an IC50 value of 0.12 mu M, was found to be three times more potent than the reference compound. In vitro stability studies showed that (S-P,S)-7c, the diastereomer of compound 7c, was stable in human blood plasma but underwent rapid metabolism to release the parent drug PMEA in liver microsomes. The possible metabolic pathway of (S-P,S)-7c in human liver microsomes was described. These findings suggest that compound (S-P,S)-7c is a promising anti-HBV drug candidate for further development. (C) 2009 Elsevier Ltd. All rights reserved.
• Hydrogen bond surrogate stabilized water soluble 310-helix from a disordered pentapeptide containing coded α-amino acids
  作者：Sunit Pal、Erode N. Prabhakaran

  DOI：10.1016/j.tetlet.2018.05.029

  日期：2018.6

  Replacing a hypothetical i + 3 → i peptide H-bond in a disordered pentapeptide, that lacks any helicogenic Cα-tetrasubstituted residues, with a propyl linker and carbamylating the N-terminal nitrogen constrains it in the elusive 310-helical structure with high helicity and stability under varying conditions of temperature and pH, confirmed by NMR and CD analyses.

  更换假想I + 3→1肽H-键无序五肽，即缺乏任何helicogenicÇ α -tetrasubstituted残基，具有丙基接头和氨甲酰化的N末端氮约束它在难以捉摸3 10具有高螺旋结构通过NMR和CD分析证实了在温度和pH值变化的条件下的螺旋度和稳定性。