α-hydroxyfuran-3-ylacetic acid | 263411-27-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: α-hydroxyfuran-3-ylacetic acid
• 英文别名: (3-furanyl)glycolic acid；2-(Furan-3-yl)-2-hydroxyacetic acid
• CAS: 263411-27-4
• 化学式: C₆H₆O₄
• 分子量: 142.111
• InChiKey: PYJAFSHQNRCHNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-hydroxyfuran-3-ylacetic acid 、 2-fluoro-4-(thien-3-yl)methoxybenzonitrile 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 3.08h， 以46%的产率得到[2-Cyano-5-(thiophen-3-ylmethoxy)-phenoxy]-furan-3-yl-acetic acid
  参考文献：
  名称：

  Selective ET_A Antagonists. 5. Discovery and Structure−Activity Relationships of Phenoxyphenylacetic Acid Derivatives

  摘要：

  The fifth paper in this series describes the culmination of our investigations into the development of a potent and selective ETA receptor antagonist for the treatment of diseases mediated by ET-1. Receptor site mapping of several ETA antagonists prepared previously identified a common cationic binding site which prompted synthesis of phenoxyphenylacetic acid derivative 13a, which showed good in vitro activity (IC50 59 nM, rat aortic ETA). Optimization of 13a led to the identification of 27b, which exhibited an IC50 of 4 nM. Although this did not translate into the expected in vivo potency, a compound of comparable in vitro activity, 27a (RPR118031A), showed a far better pharmacokinetic profile and in vivo potency (75 mu mol/kg) and was duly proposed and accepted as a development candidate.

  DOI：

  10.1021/jm990378b
• 作为产物：
  描述：

  butyl 3-furylglycolate 在 水 作用下， 生成 α-hydroxyfuran-3-ylacetic acid
  参考文献：
  名称：

  呋喃与手性乙醛酸烷基酯之间的不对称光环加成

  摘要：

  手性烷基乙醛酸酯[ R（-）-薄荷基，R（-）-和S（+）-2-辛基，R（-）-和S（+）-2、2-二甲基- [3-丁基]与呋喃的反应生成低光学纯度（2.5-7.3％）的2,7-二氧杂双环-[3.2.0]庚-3-烯-6-戊酸酯烷基化物（13a–e）。化合物13a-e异构化为3-呋喃基乙醇酸烷基酯（14a-e），收率很高。将构型S指定为3-呋喃甲氧基乙酸左旋甲基。对不对称合成的结果提出了两种解释。

  DOI：

  10.1016/0040-4020(82)80228-7

文献信息

• Piperidinyl-alpha-aminoamide modulators of chemokine receptor activity
  申请人：Zhou Cangyou

  公开号：US20050250814A1

  公开（公告）日：2005-11-10

  The present invention is directed to compounds of the formula I: (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , W, X, Z, m and n are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2.

  本发明涉及具有以下式I的化合物：（其中R1、R2、R3、R4、R5、R6、W、X、Z、m和n在此处定义），这些化合物可用作趋化因子受体活性的调节剂。特别是，这些化合物可用作趋化因子受体CCR-2的调节剂。
• Nitrilases, Nucleic Acids Encoding Them and Methods for Making and Using Them
  申请人：DeSantis Grace

  公开号：US20100009426A1

  公开（公告）日：2010-01-14

  The invention relates to nitrilases and to nucleic acids encoding the nitrilases. In addition methods of designing new nitrilases and method of use thereof are also provided. The nitrilases have increased activity and stability at increased pH and temperature.

  本发明涉及到腈酶以及编码腈酶的核酸。此外，还提供了设计新腈酶的方法和使用该方法的方法。这些腈酶在高pH和高温下具有增强的活性和稳定性。
• Nucleic Acids Encoding Nitrilases
  申请人：DESANTIS Grace

  公开号：US20110263839A1

  公开（公告）日：2011-10-27

  The invention relates to nitrilases and to nucleic acids encoding the nitrilases. In addition methods of designing new nitrilases and method of use thereof are also provided. The nitrilases have increased activity and stability at increased pH and temperature.

  该发明涉及腈水解酶以及编码腈水解酶的核酸。此外，还提供了设计新腈水解酶的方法和使用方法。该腈水解酶在高pH和高温下具有增强的活性和稳定性。
• Nitrilases, Nucleic Acids Encoding Them and Methods For Making and Using Them
  申请人：Desantis Grace

  公开号：US20120009637A1

  公开（公告）日：2012-01-12

  The invention relates to nitrilases and to nucleic acids encoding the nitrilases. In addition methods of designing new nitrilases and method of use thereof are also provided. The nitrilases have increased activity and stability at increased pH and temperature.

  该发明涉及到腈水解酶及编码腈水解酶的核酸。此外，还提供了设计新腈水解酶的方法和使用方法。这些腈水解酶在较高的pH和温度下具有增强的活性和稳定性。
• NITRILASES
  申请人：VERENIUM CORPORATION

  公开号：US20130177949A1

  公开（公告）日：2013-07-11

  The invention relates to nitrilases and to nucleic acids encoding the nitrilases. In addition methods of designing new nitrilases and method of use thereof are also provided. The nitrilases have increased activity and stability at increased pH and temperature.

  本发明涉及腈酶及编码腈酶的核酸。此外，还提供了设计新腈酶的方法以及使用该方法的方法。这些腈酶在高pH和高温下具有增强的活性和稳定性。