2-Fur-L-Thr-OMe | 1084940-95-3

• 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: 2-Fur-L-Thr-OMe
• 英文别名: (2-Fur)-Thr-OMe；methyl (2S,3R)-2-(furan-2-carbonylamino)-3-hydroxybutanoate
• CAS: 1084940-95-3
• 化学式: C₁₀H₁₃NO₅
• 分子量: 227.217
• InChiKey: WCGRUXJBZDRDNQ-SVRRBLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Fur-L-Thr-OMe 在 劳森试剂 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Modulating the Serotonin Receptor Spectrum of Pulicatin Natural Products

  摘要：

  Serotonin (5-HT) receptors are important in health and disease, but the existence of 14 subtypes necessitates selective ligands. Previously, the pulicatins were identified as ligands that specifically bound to the subtype 5-HT2B in the 500 nM to 10 mu M range and that exhibited in vitro effects on cultured mouse neurons. Here, we examined the structure activity relationship of 30 synthetic and natural pulicatin derivatives using binding, receptor functionality, and in vivo assays. The results reveal the 2-arylthiazoline scaffold as a tunable serotonin receptor-targeting pharmacophore. Tests in mice show potential antiseizure and antinociceptive activities at high doses without motor impairment.

  DOI：

  10.1021/acs.jnatprod.7b00317
• 作为产物：
  描述：

  呋喃甲酰氯 、 L-苏氨酸甲酯盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以57%的产率得到2-Fur-L-Thr-OMe
  参考文献：
  名称：

  N-酰基-β-羟基氨基酸衍生物合成取代恶唑

  摘要：

  制备了几种 N-酰基-β-羟基氨基酸，并在 4-（二甲氨基）吡啶存在下用二碳酸二叔丁酯处理，然后用 N,N,N',N'-四甲基胍处理，得到相应的N-酰基脱氢氨基酸的产率很高。然后用 I2/K2CO3 和 1,8-二氮杂双环 [5.4.0] undec-7-ene 处理这些。N-酰基脱氢氨基丁酸的甲酯以良好至高产率得到相应的取代恶唑。N-酰基脱氢苯丙氨酸与β-碘脱氢苯丙氨酸一起以低至中等产率得到5-苯基恶唑衍生物。在相同条件下，N-酰基脱氢丙氨酸不能得到相应的恶唑。然而，当反应在没有 DBU 的情况下进行时，可以分离出 β,β-二碘脱氢丙氨酸衍生物。尽管我们并不完全清楚 N-酰基脱氢氨基酸不同反应性的原因，但循环伏安法研究表明，反应性较低的衍生物具有更高的还原电位。这表明脱氢氨基丁酸衍生物中的双键更容易受到碘的亲电攻击。 (© Wiley-VCH Verlag GmbH & Co. KGaA

  DOI：

  10.1002/ejoc.200800602

文献信息

• A mild high yielding synthesis of oxazole-4-carboxylate derivatives
  作者：Paula M.T. Ferreira、Elisabete M.S. Castanheira、Luís S. Monteiro、Goreti Pereira、Helena Vilaça

  DOI：10.1016/j.tet.2010.09.014

  日期：2010.11

  Several 2,5-disubstituted oxazole-4-carboxylates were prepared in high yields from the methyl esters of N-acyl-beta-halodehydroaminobutyric acid derivatives by treatment with a 2% solution of DBU in acetonitrile. The scope of this reaction was investigated and it was found that dehydrodipeptides having a beta-bromodehydroaminobutyric acid residue gave the corresponding oxazoles in good yields. The photophysical properties of some of the oxazoles prepared were studied in four solvents of different polarity. All compounds have reasonable high fluorescence quantum yields and a moderate solvent sensitivity, which makes them good candidates to be used as fluorescent probes. One of the fluorescent oxazoles prepared was inserted after cleavage of the methyl ester into two model peptides using a conventional solution phase strategy. The photophysical properties of the labelled peptides were studied in ethanol and water and compared with those of the oxazole. The results obtained showed that the oxazole maintains a good fluorescence level and the same solvent sensitivity when linked to a peptide chain. (C) 2010 Elsevier Ltd. All rights reserved.