(S)-(2-formylfuran-5-yl)methyl 5-oxopyrrolidine-2-carboxylate | 1443763-56-1

• 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: (S)-(2-formylfuran-5-yl)methyl 5-oxopyrrolidine-2-carboxylate
• 英文别名: (S)-asfural；(5-formylfuran-2-yl)methyl (2S)-5-oxopyrrolidine-2-carboxylate
• CAS: 1443763-56-1
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: CAGSFFPKAGECCQ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  85.61
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  fructopyranose 、 L-焦谷氨酸 反应 0.33h， 以24.4 mg的产率得到(S)-(2-formylfuran-5-yl)methyl 5-oxopyrrolidine-2-carboxylate
  参考文献：
  名称：

  HYDROXYMETHYLFURFURAL DERIVATIVE

  摘要：

  公开号：

  EP2796453B1

文献信息

• Isolation, Structural Elucidation, and Biological Evaluation of a 5-Hydroxymethyl-2-furfural Derivative, Asfural, from Enzyme-Treated Asparagus Extract
  作者：Tomohiro Ito、Atsuya Sato、Tomoko Ono、Kazunori Goto、Takahiro Maeda、Jun Takanari、Hiroshi Nishioka、Kenichi Komatsu、Hideyuki Matsuura

  DOI：10.1021/jf402010c

  日期：2013.9.25

  A novel 5-hydroxymethyl-2-furfural (HMF; 1) derivative, which is named asfural (compound 2), was isolated from enzyme-treated asparagus extract (ETAS) along with HMF (1) as a heat shock protein 70 (HSP70) inducible compound. The structure of compound 2 was elucidated on the basis of its spectroscopic data from HREIMS and NMR, whereas the absolute configuration was determined using chiral HPLC analysis, compared to two synthesized compounds, (S)- and (R)-asfural. As a result, compound 2 derived from ETAS was assigned as (S)-(2-formylfuran-5-yl)methyl 5-oxopyrrolidine-2-carboxylate. When compound 2, synthesized (S)- and (R)-asfural, and HMF (1) were evaluated in terms of HSP70 mRNA expression-enhancing activity in HL-60 cells, compound 2 and (S)-asfural significantly increased the expression level in a concentration-dependent manner. HMF (1) also showed significant activity at 0.25 mg/mL.
• METHOD FOR INDUCTION OF A HEAT SHOCK PROTEIN, ANTI-STRESS OR REGULATION OF AN AUTONOMIC NERVE
  申请人：AMINO UP CHEMICAL CO., LTD.

  公开号：US20160193184A1

  公开（公告）日：2016-07-07

  A method for induction of a heat shock protein, anti-stress or regulation of an autonomic nerve comprises: administering a mammalian subject in need thereof a composition comprising an effective amount of hydroxymethylfurfural derivative of the following formula: wherein R is selected from the group consisting of formula (I): (II): HOOCCH 2 COCO—, (III): HOOCCH 2 CH 2 COCO—, and (IV): a hydrogen atom.
• US9359321B2
  申请人：——

  公开号：US9359321B2

  公开（公告）日：2016-06-07
• US9610279B2
  申请人：——

  公开号：US9610279B2

  公开（公告）日：2017-04-04
• HYDROXYMETHYLFURFURAL DERIVATIVE
  申请人：Amino Up Chemical Co., Ltd.

  公开号：EP2796453B1

  公开（公告）日：2019-05-22