2-(3-Carbamoylphenoxy)acetic acid | 500866-01-3

• 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: 2-(3-Carbamoylphenoxy)acetic acid
• CAS: 500866-01-3
• 化学式: C₉H₉NO₄
• mdl: MFCD09943019
• 分子量: 195.175
• InChiKey: DCZLMOYGKHSTTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  409.0±25.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-Carbamoylphenoxy)acetic acid 、 乙酸酐 、 Fmoc-Lys(Dde)-OH 以84%的产率得到2-(3-((5-acetamido-6-amino-6-oxohexylamino)methyl)phenoxy)acetic acid
  参考文献：
  名称：

  Aminodeoxychorismate Synthase Inhibitors from One-Bead One-Compound Combinatorial Libraries:  “Staged” Inhibitor Design

  摘要：

  4-Amino-4-deoxychorismate synthase (ADCS) catalyzes the first step in the conversion of chorismate into p-aminobenzoate, which is incorporated into folic acid. We aim to discover compounds that inhibit ADCS and serve as leads for a new class of antimicrobial compounds. This report presents (1) synthesis of a mass-tag encoded library based on a "staged" design, (2) massively parallel fluorescence-based on-bead screening, (3) rapid structural identification of hits, and (4) full kinetic analysis of ADCS. All inhibitors are competitive against chorismate and Mg2+. The most potent ADCS inhibitor identified has a K-i of 360 mu M. We show that the combinatorial diversity elements add substantial binding affinity by interacting with residues outside of but proximal to the active site. The methods presented here constitute a paradigm for inhibitor discovery through active site targeting, enabled by rapid library synthesis, facile massively parallel screening, and straightforward hit identification.

  DOI：

  10.1021/jm0609869
• 作为产物：
  描述：

  3-羧基苯氧基乙酸 在 4-二甲氨基吡啶 1-羟基苯并三唑 、 Rink amide MBHA resin 、 N,N'-二异丙基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 2-(3-Carbamoylphenoxy)acetic acid
  参考文献：
  名称：

  Aminodeoxychorismate Synthase Inhibitors from One-Bead One-Compound Combinatorial Libraries:  “Staged” Inhibitor Design

  摘要：

  4-Amino-4-deoxychorismate synthase (ADCS) catalyzes the first step in the conversion of chorismate into p-aminobenzoate, which is incorporated into folic acid. We aim to discover compounds that inhibit ADCS and serve as leads for a new class of antimicrobial compounds. This report presents (1) synthesis of a mass-tag encoded library based on a "staged" design, (2) massively parallel fluorescence-based on-bead screening, (3) rapid structural identification of hits, and (4) full kinetic analysis of ADCS. All inhibitors are competitive against chorismate and Mg2+. The most potent ADCS inhibitor identified has a K-i of 360 mu M. We show that the combinatorial diversity elements add substantial binding affinity by interacting with residues outside of but proximal to the active site. The methods presented here constitute a paradigm for inhibitor discovery through active site targeting, enabled by rapid library synthesis, facile massively parallel screening, and straightforward hit identification.

  DOI：

  10.1021/jm0609869

文献信息

• US5215738A
  申请人：——

  公开号：US5215738A

  公开（公告）日：1993-06-01
• [EN] BENZAMIDE AND NICOTINAMIDE RADIOSENSITIZERS
  申请人：SRI INTERNATIONAL

  公开号：WO1986006628A1

  公开（公告）日：1986-11-20

  (EN) Method for sensitizing hypoxic tumor cells to radiation using dervatives of benzamide and nicotinamide. Some of the compounds useful in the method of the invention are novel.(FR) Un procédé consiste à utiliser des dérivés de benzamide et de nicotinamide pour sensibiliser des cellules tumorales hypoxygénées aux rayonnements. Certains composés utilisés dans ce procédé sont nouveaux.
• Aminodeoxychorismate Synthase Inhibitors from One-Bead One-Compound Combinatorial Libraries:  “Staged” Inhibitor Design
  作者：Seth Dixon、Kristin T. Ziebart、Ze He、Melissa Jeddeloh、Choong Leol Yoo、Xiaobing Wang、Alan Lehman、Kit S. Lam、Michael D. Toney、Mark J. Kurth

  DOI：10.1021/jm0609869

  日期：2006.12.1

  4-Amino-4-deoxychorismate synthase (ADCS) catalyzes the first step in the conversion of chorismate into p-aminobenzoate, which is incorporated into folic acid. We aim to discover compounds that inhibit ADCS and serve as leads for a new class of antimicrobial compounds. This report presents (1) synthesis of a mass-tag encoded library based on a "staged" design, (2) massively parallel fluorescence-based on-bead screening, (3) rapid structural identification of hits, and (4) full kinetic analysis of ADCS. All inhibitors are competitive against chorismate and Mg2+. The most potent ADCS inhibitor identified has a K-i of 360 mu M. We show that the combinatorial diversity elements add substantial binding affinity by interacting with residues outside of but proximal to the active site. The methods presented here constitute a paradigm for inhibitor discovery through active site targeting, enabled by rapid library synthesis, facile massively parallel screening, and straightforward hit identification.