ortho-phenylenediamine-N-acetic acid

• 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: ortho-phenylenediamine-N-acetic acid
• 英文别名: N-(2-Aminophenyl)glycine；2-(2-aminoanilino)acetic acid
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: BMQNQXULEJLLIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ortho-phenylenediamine-N-acetic acid 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(3-chloro-2-oxoquinoxalin-1-yl)acetic acid
  参考文献：
  名称：

  Synthesis and evaluation of 3-anilino-quinoxalinones as glycogen phosphorylase inhibitors

  摘要：

  A series of 3-anilino-quinoxalinones has been identified as a new class of glycogen phosphorylase inhibitors. The lead compound I was identified through high throughput screening as well as through pharmacophore-based electronic screening. Modifications were made to the scaffold of 1 to produce novel analogues, some of which are 25 times more potent than the lead compound. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.021
• 作为产物：
  描述：

  N-鄰硝苯甘胺酸 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 ortho-phenylenediamine-N-acetic acid
  参考文献：
  名称：

  Synthesis and evaluation of 3-anilino-quinoxalinones as glycogen phosphorylase inhibitors

  摘要：

  A series of 3-anilino-quinoxalinones has been identified as a new class of glycogen phosphorylase inhibitors. The lead compound I was identified through high throughput screening as well as through pharmacophore-based electronic screening. Modifications were made to the scaffold of 1 to produce novel analogues, some of which are 25 times more potent than the lead compound. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.021

文献信息

• Structure–biodistribution relation of neutral 99mTc(CO)3-complexes with tridentate N-substituted derivatives of aminoethylglycine and phenylenediamine
  作者：Dirk Rattat、Jan Cleynhens、Christelle Terwinghe、An-Elisabeth De Greve、Alfons Verbruggen

  DOI：10.1016/j.tetlet.2006.04.136

  日期：2006.7

  Derivatives of ethylenediamine-N-acetic acid (EDAA = N-aminoethylglycine = AEG) and ortho-phenylenediamine-N-acetic acid (PDAA) with uncharged substituents on one or both of the amines form neutral complexes with a [Tc-99m(CO)(3)](+)-moiety. We studied the influence of different modifications at the amines (e.g., with methyl, ethyl, butyl or benzyl groups) on the behaviour of the Tc-99m(CO)(3)-complexes in vivo in mice, with special focus on blood-brain barrier (BBB) passage. The complexes have been characterised by reversed phase HPLC, log P. electrophoresis and some of them also by LC-MS. LogP values of the Tc-99m-tricarbonyl complexes varied from -0.52 (AEG) to 2.5 (N'N'-dibenzyl-EDAA). With increasing lipophilicity, more of the activity was found in liver and intestines as compared to kidneys and urine for the more polar complexes. Brain uptake was found for the Tc-99m(CO)(3)-complexes with N,N'-dibutyl-ethylenediamine-N-acetic acid (0.34% of I.D. after 2 min) and ortho-phenylenediamine-N-acetic acid (0.22% of I.D. after 2 min). (c) 2006 Elsevier Ltd. All rights reserved.
• A METHOD AND LIQUID COMPOSITION FOR THE PRODUCTION OF INDELIBLE SCRIPT ON A PAPER SUBSTRATE
  申请人：SEGALLA, Gabriele

  公开号：EP0633915A1

  公开（公告）日：1995-01-18
• NOVEL PEPTIDE, ACTIVE AS INHIBITORS OF PLATELET AGGREGATION
  申请人：NIPPON STEEL CORPORATION

  公开号：EP0721468A1

  公开（公告）日：1996-07-17
• AMIDE BASED GLUCAGON SUPERFAMILY PEPTIDE PRODRUGS
  申请人：Indiana University Research and Technology Corporation

  公开号：EP2588126A2

  公开（公告）日：2013-05-08
• PRODRUGS WITH PROLONGED ACTION
  申请人：Indiana University Research and Technology Corporation

  公开号：EP2986314A2

  公开（公告）日：2016-02-24