2-(甲基氨基)-苯甲酸 2,5-二氧代-1-吡咯烷基酯 | 64156-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(甲基氨基)-苯甲酸 2,5-二氧代-1-吡咯烷基酯
• 中文别名: 2-(甲基氨基)-苯甲酸2,5-二氧代-1-吡咯烷基酯
• 英文名称: 2-methylaminobenzoic acid 2,5-dioxopyrrolidin-1-yl ester
• 英文别名: N-methyl anthranilic acid succinimidyl ester；Succinimidyl N-methylanthranilate；(2,5-dioxopyrrolidin-1-yl) 2-(methylamino)benzoate
• CAS: 64156-72-5
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.238
• InChiKey: UNICSTUDFDPGRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2925190090

反应信息

• 作为反应物：
  描述：

  ((S)-4-(8-aminooctanamido)cyclopent-1-en-1-yl)(butyl)phosphinic acid 、 2-(甲基氨基)-苯甲酸 2,5-二氧代-1-吡咯烷基酯 在 碳酸氢钠 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 16.0h， 以78%的产率得到((S)-4-(8-(2-(methylamino)benzamido)octanamido)cyclopent-1-en-1-yl)(butyl)phosphinic acid
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Fluorescent and Biotinylated Antagonists of ρ₁ GABA_C Receptors

  摘要：

  The rho(1) GABA(C) receptor is a ligand-gated chloride ion channel that shows promise as a therapeutic target for myopia, sleep disorders, memory and learning facilitation, and anxiety-related disorders. As such, there is a need for molecular probes to understand the role GABA(C) receptors play in physiological and pathological processes. To date, no labeled (either radioactive or fluorescent) GABA(C) selective ligand has been developed that can act as a marker for GABA(C) receptor visualization and localization studies. Herein, we report a series of fluorescent ligands containing different-sized linkers and fluorophores based around (S)-4-ACPBPA [(4-aminocyclopenten-1-yl)-butylphosphinic acid], a selective GABA(C) antagonist. One of these conjugates, (S)-4-ACPBPA-C5-BODIPY (13), displayed moderate potency (IC50 = 58.61 mu M) and selectivity (>100 times) for rho(1) over alpha(1)beta(2)gamma(2L) GABA(A) receptors. These conjugates are novel lead agents for the development of more potent and selective fluorescent probes for studying the localization and function of GABA(C) receptors in living cells.

  DOI：

  10.1021/ml300476v
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 N-甲基蒽 在 N,N'-二环己基碳二亚胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 48.0h， 以88%的产率得到2-(甲基氨基)-苯甲酸 2,5-二氧代-1-吡咯烷基酯
  参考文献：
  名称：

  Reactions of N-Hydroxysuccinimide Esters of Anthranilic Acids with Anions of .BETA.-Keto Esters. A New Route to 4-Oxo-3-quinolinecarboxylic Acid Derivatives.

  摘要：

  本文介绍了一种合成 4-氧代-3-喹啉羧酸衍生物的新方法。该方法包括将适当的 β-酮酯阴离子与新型 N-羟基琥珀酰亚胺蒽酸酯进行 C-酰化。中间的 C-酰化产物 3 自发环化生成 3-乙氧羰基-4-氧代喹啉衍生物 4。通过选择合适的蒽酸和 β-酮酯，可以在喹啉环的阳离子 1 和 2 上引入各种取代基。红外光谱和核磁共振光谱数据证实了所获得的 2-取代 3-乙氧羰基-4-氧代喹啉的结构。

  DOI：

  10.1248/cpb.48.211

文献信息

• Reactions of N-Hydroxysuccinimide Esters of Anthranilic Acids with Anions of .BETA.-Keto Esters. A New Route to 4-Oxo-3-quinolinecarboxylic Acid Derivatives.
  作者：Christos MITSOS、Alexandros ZOGRAFOS、Olga IGGLESSI-MARKOPOULOU

  DOI：10.1248/cpb.48.211

  日期：——

  A new approach for the synthesis of 4-oxo-3-quinolinecarboxylic acid derivtives is described. This methodology involves the C-acylation of the anions of appropriate β-keto esters with novel N-hydroxysuccinimide esters of anthranilic acids. The intermediate C-acylation products 3 are spontaneously cyclized to afford 3-ethoxycarbonyl-4-oxoquinoline derivatives 4. The introduction of a variety of substituents at positins 1 and 2 of the quinoline ring is feasible with the selection of suitable anthranilic acids and β-keto esters. The structure of the obtained 2-substituted 3-ethoxycarbonyl-4-oxoquinolines was confirmed by IR and NMR spectral data.

  本文介绍了一种合成 4-氧代-3-喹啉羧酸衍生物的新方法。该方法包括将适当的 β-酮酯阴离子与新型 N-羟基琥珀酰亚胺蒽酸酯进行 C-酰化。中间的 C-酰化产物 3 自发环化生成 3-乙氧羰基-4-氧代喹啉衍生物 4。通过选择合适的蒽酸和 β-酮酯，可以在喹啉环的阳离子 1 和 2 上引入各种取代基。红外光谱和核磁共振光谱数据证实了所获得的 2-取代 3-乙氧羰基-4-氧代喹啉的结构。
• Affinity fishing for ligands and proteins receptors
  申请人：Novo Nordisk A/S

  公开号：EP2053403A2

  公开（公告）日：2009-04-29

  The invention provides putative "drugable" protein targets and actively binding ligands identified in an efficient and reproducible process by determining the affinity of protein mixtures to libraries of ligand compounds of defined size and composition. The libraries are used to isolate and identify previously unknown corresponding protein-ligand binding pairs from a mixture of proteins and a library of compounds, and are particularly useful to identify differentially selective protein-ligand binding pairs, for example, representing a single physiological state or several varied but related states, such as disease versus normal conditions. The invention also provides processes for identifying such protein-ligand binding pairs.

  本发明通过确定蛋白质混合物与确定大小和组成的配体化合物库的亲和力，以高效和可重复的过程鉴定推定的 "可药 "蛋白质靶标和活性结合配体。配体化合物库用于从蛋白质混合物和化合物库中分离和鉴定先前未知的相应蛋白质配体结合对，特别适用于鉴定具有不同选择性的蛋白质配体结合对，例如，代表单一生理状态或几种不同但相关的状态，如疾病与正常状态。本发明还提供了鉴定此类蛋白质配体结合对的方法。
• Non-destructive quality control method for microarray substrate coatings via labeled doping
  申请人：Conzone D. Samuel

  公开号：US20060003376A1

  公开（公告）日：2006-01-05

  A non-destructive method of determining the uniformity of a coating on a substrate comprises coating the substrate with a homogenous coating mixture comprising a labeled compound and a chemically functional compound to which other chemical moieties can be bound, and detecting the presence and locations of the labeled compound on the surface. The invention also relates to a surface for attachment of molecules comprising a substrate and a coating thereon of a homogeneous mixture of a labeled compound and a first chemically functional compound to which other chemical moieties can be bound.

  一种确定基底上涂层均匀性的非破坏性方法包括用均质涂层混合物涂覆基底，该混合物包括标记化合物和可结合其它化学分子的化学功能化合物，并检测表面上标记化合物的存在和位置。本发明还涉及一种用于附着分子的表面，该表面包括一个基底和一层由标记化合物和第一化学功能化合物组成的均质混合物涂层，第一化学功能化合物可与其他化学分子结合。
• AFFINITY FISHING FOR LIGANDS AND PROTEINS RECEPTORS
  申请人：Novo Nordisk A/S

  公开号：EP1588173B1

  公开（公告）日：2008-11-26
• Affinity screening using "one-bead-one-compound" libraries
  申请人：St. Hilaire Marie Phaedria

  公开号：US20060257875A1

  公开（公告）日：2006-11-16

  The invention provides putative “drugable” protein targets and actively binding ligands identified in an efficient and reproducible process by determining the affinity of protein mixtures to libraries of ligand compounds of defined size and composition. The libraries are used to isolate and identify previously unknown corresponding protein-ligand binding pairs from a mixture of proteins and a library of compounds, and are particularly useful to identify differentially selective protein-ligand binding pairs, for example, representing a single physiological state or several varied but related states, such as disease versus normal conditions. The invention also provides processes for identifying such protein-ligand binding pairs.