((3-nitro-phenyl)-methyl-amino)-acetic acid | 942232-50-0

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: ((3-nitro-phenyl)-methyl-amino)-acetic acid
• 英文别名: [methyl(3-nitrophenyl)amino]acetic acid；2-(N-methyl-3-nitroanilino)acetic acid
• CAS: 942232-50-0
• 化学式: C₉H₁₀N₂O₄
• 分子量: 210.189
• InChiKey: JRKPUAYEPNTVLU-UHFFFAOYSA-N

物化性质

• 沸点：
  408.3±25.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((3-nitro-phenyl)-methyl-amino)-acetic acid 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 methyl 2-[3-[[2-[5-cyclohexyl-1-(3,3-dimethyl-2-oxobutyl)-2-oxo-1,3,4-benzotriazepin-3-yl]acetyl]amino]-N-methylanilino]acetate
  参考文献：
  名称：

  Optimization of 1,3,4-Benzotriazepine-Based CCK₂ Antagonists to Obtain Potent, Orally Active Inhibitors of Gastrin-Mediated Gastric Acid Secretion

  摘要：

  Starting from a novel, achiral 1,3,4-benzotriazepine-based CCK2 receptor antagonist, a process of optimization has afforded further compounds of this type that maintain the nanomolar affinity for recombinant, human CCK2 receptors and high selectivity over CCK1 receptors observed in the initial lead but display more potent inhibition of pentagastrin-stimulated gastric acid secretion in vivo. Moreover, this has largely been achieved without altering their potency at wild-type canine and rat receptors, as judged by their displacement of [I-125]-BH-CCK-8S in a radioligand binding assay and by their activity in an isolated, perfused rat stomach bioassay, respectively. 2-(5-Cyclohexyl-1-(2-cyclopentyl-2-oxo-ethyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl)-N-(3-(5-oxo-2,5-dihydro- [1,2,4]oxadiazol-3-yl)-phenyl)-acetamide (47) was identified as the most effective compound stemming from this approach, proving to be a potent inhibitor of pentagastrin-stimulated gastric acid secretion in rats and dogs by intravenous bolus as well as by enteral administration.

  DOI：

  10.1021/jm070139l
• 作为产物：
  描述：

  间硝基苯胺 在 盐酸 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 35.5h， 生成 ((3-nitro-phenyl)-methyl-amino)-acetic acid
  参考文献：
  名称：

  [EN] PIPERIDINE-2,6-DIONES AS SMALL MOLECULE DEGRADERS OF HELIOS AND METHODS OF USE
  [FR] PIPÉRIDINE-2,6-DIONES UTILISÉES COMME AGENTS DE DÉGRADATION À PETITES MOLÉCULES D'HÉLIOS ET MÉTHODES D'UTILISATION

  摘要：

  本文披露了一些化合物及其药用盐、水合物、溶剂合物、前药、立体异构体和互变异构体，这些化合物可能导致各种蛋白质的降解，例如IKZF2（Helios）。同时还披露了含有这些化合物的药物组合物，以及使用这些化合物治疗与Helios相关的疾病和障碍，并可能从Helios降解中受益的方法。

  公开号：

  WO2021236885A1

文献信息

• Optimization of 1,3,4-Benzotriazepine-Based CCK₂ Antagonists to Obtain Potent, Orally Active Inhibitors of Gastrin-Mediated Gastric Acid Secretion
  作者：Iain M. McDonald、James W. Black、Ildiko M. Buck、David J. Dunstone、Eric P. Griffin、Elaine A. Harper、Robert A. D. Hull、S. Barret Kalindjian、Elliot J. Lilley、Ian D. Linney、Michael J. Pether、Sonia P. Roberts、Mark E. Shaxted、John Spencer、Katherine I. M. Steel、David A. Sykes、Martin K. Walker、Gillian F. Watt、Laurence Wright、Paul T. Wright、Wei Xun

  DOI：10.1021/jm070139l

  日期：2007.6.1

  Starting from a novel, achiral 1,3,4-benzotriazepine-based CCK2 receptor antagonist, a process of optimization has afforded further compounds of this type that maintain the nanomolar affinity for recombinant, human CCK2 receptors and high selectivity over CCK1 receptors observed in the initial lead but display more potent inhibition of pentagastrin-stimulated gastric acid secretion in vivo. Moreover, this has largely been achieved without altering their potency at wild-type canine and rat receptors, as judged by their displacement of [I-125]-BH-CCK-8S in a radioligand binding assay and by their activity in an isolated, perfused rat stomach bioassay, respectively. 2-(5-Cyclohexyl-1-(2-cyclopentyl-2-oxo-ethyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl)-N-(3-(5-oxo-2,5-dihydro- [1,2,4]oxadiazol-3-yl)-phenyl)-acetamide (47) was identified as the most effective compound stemming from this approach, proving to be a potent inhibitor of pentagastrin-stimulated gastric acid secretion in rats and dogs by intravenous bolus as well as by enteral administration.
• [EN] PIPERIDINE-2,6-DIONES AS SMALL MOLECULE DEGRADERS OF HELIOS AND METHODS OF USE<br/>[FR] PIPÉRIDINE-2,6-DIONES UTILISÉES COMME AGENTS DE DÉGRADATION À PETITES MOLÉCULES D'HÉLIOS ET MÉTHODES D'UTILISATION
  申请人：DANA FARBER CANCER INST INC

  公开号：WO2021236885A1

  公开（公告）日：2021-11-25

  Disclosed are compounds and pharmaceutically acceptable salts, hydrates, solvates, prodrugs, stereoisomers, and tautomers thereof that may cause degradation of various proteins e.g., IKZF2 (Helios). Also disclosed are pharmaceutical compositions containing same, and methods of making and using the compounds to treat diseases and disorders associated with Helios and which may benefit from Helios degradation.

  本文披露了一些化合物及其药用盐、水合物、溶剂合物、前药、立体异构体和互变异构体，这些化合物可能导致各种蛋白质的降解，例如IKZF2（Helios）。同时还披露了含有这些化合物的药物组合物，以及使用这些化合物治疗与Helios相关的疾病和障碍，并可能从Helios降解中受益的方法。