3-氨基-3-(2-硝基苯基)丙酸甲酯 | 287959-40-4

• 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
• 中文名称: 3-氨基-3-(2-硝基苯基)丙酸甲酯
• 英文名称: methyl 3-amino-3-(2-nitrophenyl)propionate
• 英文别名: Methyl 3-amino-3-(2-nitrophenyl)propanoate
• CAS: 287959-40-4
• 化学式: C₁₀H₁₂N₂O₄
• mdl: MFCD18907620
• 分子量: 224.216
• InChiKey: SJWDOSCKIYWKEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  98.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-氨基-3-(2-硝基苯基)丙酸甲酯 生成 methyl 3-(2-aminoacetylamino)-3-(2-nitrophenyl)propionate hydrochloride
  参考文献：
  名称：

  &bgr;-alanine derivatives

  摘要：

  本发明涉及公式（I）的&bgr;-丙氨酸衍生物，其中Q1，Q2，Q3，Q4，R1，R2，R3，R4，R5，R6和n的含义如公开说明书所述，并且它们的生理上可接受的盐或溶剂。该物质是整合素抑制剂，可用于治疗血栓形成、心肌梗死、冠心病、动脉硬化、炎症、肿瘤、骨质疏松、感染以及血管生成诱导或促进的病理过程中的再狭窄。

  公开号：

  US06576637B1
• 作为产物：
  描述：

  邻硝基苯甲醛 在 氯化亚砜 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 3-氨基-3-(2-硝基苯基)丙酸甲酯
  参考文献：
  名称：

  Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1)

  摘要：

  All-trans-retinoic acid (ATRA), the biologically active metabolite of vitamin A, is used medicinally for the treatment of hyperproliferative diseases and cancers. However, it is easily metabolized. In this study, the leading compound S8 was found based on virtual screening. To improve the activity of the leading compound S8, a series of novel S8 derivatives were designed, synthesized and evaluated for their in vitro biological activities.All of the prepared compounds showed that substituting the 5-chloro-3-methyl-1-phenyl-1H-pyrazole group for the 2-tertbutyl-5-methylfuran scaffold led to a clear increase in the biological activity. The most promising compound 32, with a CYP26A1 IC50 value of 1.36 mu M (compared to liarozole (IC50 = 2.45 mu M) and S8 (IC50 = 3.21 mu M)) displayed strong inhibitory and differentiation activity against HL60 cells. In addition, the study focused on the effect of beta-phenylalanine, which forms the coordination bond with the heme of CYP26A1. These studies suggest that the compound 32 can be used as an appropriate candidate for future development. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.036

文献信息

• Design and synthesis of novel potent and selective integrin αvβ3 antagonists—Novel synthetic routes to isoquinolinone, benzoxazinone, and quinazolinone acetates
  作者：Werner Seitz、Hervé Geneste、Gisela Backfisch、Jürgen Delzer、Claudia Graef、Wilfried Hornberger、Andreas Kling、Thomas Subkowski、Norbert Zimmermann

  DOI：10.1016/j.bmcl.2007.11.089

  日期：2008.1

  An unexpected ring contraction of benzazepinone based alpha(nu)beta(3) antagonists led to the design of quinolinone-type derivatives. Novel and efficient synthetic routes to isoquinolinone, benzoxazinone, and quinazolinone acetates were established. Nanomolar alpha(nu)beta(3) antagonists based on these new scaffolds were prepared. Moreover, benzoxazinones 15a and 15b exhibited high microsomal stability

  基于苯并ze庚酮的α（nu）beta（3）拮抗剂的意外环收缩导致了喹啉酮型衍生物的设计。建立了新颖，有效的合成异喹啉酮，苯并恶嗪酮和喹唑啉酮乙酸酯的途径。制备了基于这些新支架的纳摩尔α（nu）β（3）拮抗剂。此外，苯并恶嗪酮15a和15b表现出高的微粒体稳定性和良好的渗透性。
• [EN] CELL ADHESION INHIBITORS<br/>[FR] INHIBITEURS DE L'ADHERENCE CELLULAIRE
  申请人：BIOGEN, INC.

  公开号：WO1996022966A1

  公开（公告）日：1996-08-01

  (EN) The present invention relates to novel compounds that are useful for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies. This invention also relates to pharmaceutical formulations comprising these compounds and methods of using them for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies. The compounds and pharmaceutical compositions of this invention can be used as therapeutic or prophylactic agents. They are particularly well-suited for treatment of many inflammatory and autoimmune diseases.(FR) L'invention concerne de nouveaux composés utiles pour inhiber et prévenir l'adhérence cellulaire, ainsi que les pathologies provoquées par l'adhérence cellulaire. Elle concerne également des compositions pharmaceutiques contenant ces composés, ainsi que des procédés permettant de les utiliser pour inhiber et prévenir l'adhérence cellulaire et les pathologies provoquées par l'adhérence cellulaire. On peut utiliser ces composés et ces compositions pharmaceutiques en tant qu'agents thérapeutiques et prophylactiques. Ils sont particulièrement appropriés pour le traitement de nombreuses maladies inflammatoires et auto-immunes.

  本发明涉及新型化合物，可用于抑制和预防细胞黏附和细胞黏附介导的病理过程。本发明还涉及包含这些化合物的制药配方和使用它们抑制和预防细胞黏附和细胞黏附介导的病理过程的方法。本发明的化合物和制药组合物可用作治疗或预防剂。它们特别适用于治疗许多炎症和自身免疫性疾病。
• Cell adhesion inhibitors
  申请人：——

  公开号：US20030018016A1

  公开（公告）日：2003-01-23

  The present invention relates to novel compounds that are useful for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies. This invention also relates to pharmaceutical formulations comprising these compounds and methods of using them for inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies. The compounds and pharmaceutical compositions of this invention can be used as therapeutic or prophylactic agents. They are particularly well-suited for treatment of many inflammatory and autoimmune diseases.

  本发明涉及新型化合物，其对细胞粘附和细胞粘附介导的病理过程的抑制和预防具有用处。本发明还涉及包含这些化合物的制药配方和使用它们抑制和预防细胞粘附和细胞粘附介导的病理过程的方法。本发明的化合物和制药组合物可用作治疗或预防剂。它们特别适用于治疗许多炎症和自身免疫性疾病。
• Synthesis, in Vitro and in Vivo Biological Evaluation, and Comprehensive Understanding of Structure−Activity Relationships of Dipeptidyl Boronic Acid Proteasome Inhibitors Constructed from β-Amino Acids
  作者：Yongqiang Zhu、Gang Wu、Xinrong Zhu、Yuheng Ma、Xin Zhao、Yuejie Li、Yunxia Yuan、Jie Yang、Sen Yu、Feng Shao、Meng Lei

  DOI：10.1021/jm1009742

  日期：2010.12.23

  An extensive structure-activity relationship (SAR) study of 72 dipeptidyl boronic acid proteasome inhibitors constructed from beta-amino acids is reported. SAR analysis revealed that bicyclic groups at the RI position, 3-F substituents at the R-2 position, and bulky aliphatic groups at the R-3 position were favorable to the activities. Enzymatic screening results showed that compound 78, comprising all of these features, was the most active inhibitor against the 20S human proteasome at less than a 2 nM level, as active as the marketed drug bortezomib. Cellular assays confirmed that compound 78 was the most potent against two hematologic and some solid tumor cells with IC50 values less than 1 mu M. Pharmacokinetic profiles suggested that 78 showed higher plasma exposure and a longer half-life than bortezomib.
• CELL ADHESION INHIBITORS
  申请人：BIOGEN, INC.

  公开号：EP0805796B1

  公开（公告）日：2002-12-11