3-(3,5-Difluorophenyl)-2-oxopropanoic acid | 390387-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3,5-Difluorophenyl)-2-oxopropanoic acid
• CAS: 390387-79-8
• 化学式: C₉H₆F₂O₃
• 分子量: 200.142
• InChiKey: ABQNNXIBZSKYFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3,5-Difluorophenyl)-2-oxopropanoic acid 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  Optimization and Mechanistic Studies of Psammaplin A Type Antibacterial Agents Active against Methicillin-ResistantStaphylococcus aureus (MRSA)

  摘要：

  As described in the preceding article, utilizing a novel combinatorial disulfide exchange strategy, a library of psammaplin A (1) analogues was constructed and screened for antibacterial activity leading to the identification of a collection of diverse lead compounds. These combinatorial leads were subsequently refined, through parallel synthesis, to afford a series of highly potent antibacterial agents (e.g. 17. 57, 58, 69, and 70). some possessing greater than 50-fold higher activities than the natural product. Evaluation of the selectivity and serum binding properties of some of the most promising compounds and preliminary studies directed at deciphering the mechanism of action of this novel class of antibacterial agents are also included.

  DOI：

  10.1002/1521-3765(20011001)7:19<4296::aid-chem4296>3.0.co;2-2
• 作为产物：
  描述：

  L-3,5-二氟苯丙氨酸 在 水 、 氧气 作用下， 生成 3-(3,5-Difluorophenyl)-2-oxopropanoic acid
  参考文献：
  名称：

  苯丙氨酸氨裂解酶合成 D-和 L-苯丙氨酸衍生物：多酶级联过程

  摘要：

  通过将苯丙氨酸解氨酶 (PAL) 胺化与化学酶脱外消旋（基于立体选择性氧化和非选择性还原）。还开发了一种简单的高通量固相筛选方法来鉴定具有较高非天然D-苯丙氨酸形成率的 PAL。在化学酶级联中利用了最佳变体，从而提高了D配置产品的产量和 ee 值。此外，该系统还扩展到制备低浓度的L-苯丙氨酸。ee 值使用PAL胺化。

  DOI：

  10.1002/anie.201410670

文献信息

• Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment
  作者：Ayako Yamashita、Emily B. Norton、Joshua A. Kaplan、Chuan Niu、Frank Loganzo、Richard Hernandez、Carl F. Beyer、Tami Annable、Sylvia Musto、Carolyn Discafani、Arie Zask、Semiramis Ayral-Kaloustian

  DOI：10.1016/j.bmcl.2004.08.024

  日期：2004.11

  Analogs of hemiasterlin (1) and HTI-286 (2), which contain various aromatic rings in the A segment, were synthesized as potential inhibitors of tubulin polymerization. The structure-activity relationships related to stereo- and regio-chemical effects of substituents on the aromatic ring in the A segment were studied. Analogs, which carry a meta-substituted phenyl ring in the A segment show comparable activity for inhibition of tubulin polymerization to 2, as well as in the cell proliferation assay using KB cells containing P-glycoprotein, compared to those of 1 and 2. (C) 2004 Elsevier Ltd. All rights reserved.
• Optimization and Mechanistic Studies of Psammaplin A Type Antibacterial Agents Active against Methicillin-ResistantStaphylococcus aureus (MRSA)
  作者：K. C. Nicolaou、Robert Hughes、Jeffrey A. Pfefferkorn、Sofia Barluenga

  DOI：10.1002/1521-3765(20011001)7:19<4296::aid-chem4296>3.0.co;2-2

  日期：2001.10.1

  As described in the preceding article, utilizing a novel combinatorial disulfide exchange strategy, a library of psammaplin A (1) analogues was constructed and screened for antibacterial activity leading to the identification of a collection of diverse lead compounds. These combinatorial leads were subsequently refined, through parallel synthesis, to afford a series of highly potent antibacterial agents (e.g. 17. 57, 58, 69, and 70). some possessing greater than 50-fold higher activities than the natural product. Evaluation of the selectivity and serum binding properties of some of the most promising compounds and preliminary studies directed at deciphering the mechanism of action of this novel class of antibacterial agents are also included.
• Synthesis of<scp>D</scp>- and<scp>L</scp>-Phenylalanine Derivatives by Phenylalanine Ammonia Lyases: A Multienzymatic Cascade Process
  作者：Fabio Parmeggiani、Sarah L. Lovelock、Nicholas J. Weise、Syed T. Ahmed、Nicholas J. Turner

  DOI：10.1002/anie.201410670

  日期：2015.4.7

  phenylalanine ammonia lyase (PAL) amination with a chemoenzymatic deracemization (based on stereoselective oxidation and nonselective reduction). A simple high‐throughput solid‐phase screening method has also been developed to identify PALs with higher rates of formation of non‐natural D‐phenylalanines. The best variants were exploited in the chemoenzymatic cascade, thus increasing the yield and ee value

  通过将苯丙氨酸解氨酶 (PAL) 胺化与化学酶脱外消旋（基于立体选择性氧化和非选择性还原）。还开发了一种简单的高通量固相筛选方法来鉴定具有较高非天然D-苯丙氨酸形成率的 PAL。在化学酶级联中利用了最佳变体，从而提高了D配置产品的产量和 ee 值。此外，该系统还扩展到制备低浓度的L-苯丙氨酸。ee 值使用PAL胺化。