{2-[(2-bromomethylacryloyl)-(2,4-dimethoxybenzyl)amino]-4-ethylpentanoylamino}acetic acid ethyl ester | 1353048-87-9

• 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: {2-[(2-bromomethylacryloyl)-(2,4-dimethoxybenzyl)amino]-4-ethylpentanoylamino}acetic acid ethyl ester
• 英文别名: ethyl 2-(2-(2-(bromomethyl)-N-(2,4-dimethoxybenzyl)acrylamido)-4-methylpentaneamido)acetate；ethyl 2-[[2-[2-(bromomethyl)prop-2-enoyl-[(2,4-dimethoxyphenyl)methyl]amino]-4-methylpentanoyl]amino]acetate
• CAS: 1353048-87-9
• 化学式: C₂₃H₃₃BrN₂O₆
• 分子量: 513.429
• InChiKey: XCXZLPSGEDZZND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {2-[(2-bromomethylacryloyl)-(2,4-dimethoxybenzyl)amino]-4-ethylpentanoylamino}acetic acid ethyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.0h， 生成 2,6-dichlorobenzoic acid 2-[1-(ethoxycarbonylmethylcarbamoyl)-3-methylbutylcarbamoyl]allyl ester
  参考文献：
  名称：

  Studies toward Novel Peptidomimetic Inhibitors of Thioredoxin–Thioredoxin Reductase System

  摘要：

  Thioredoxins (Trx) are ubiquitous multifunctional low-molecular weight proteins that together with thioredoxin reductases (TrxR) participate in the maintenance of protein thiol homeostasis in NADPH-dependent reactions. An increasing number of data reveal that the Trx-TrxR system is an attractive target for anticancer therapies. In this work, we have elaborated a new and simple synthetic approach employing Ugi reaction to synthesize several new inhibitors of this system. The influence of various electrophilic fragments of this new class of compounds on the inhibition of the Trx-TrxR system was evaluated. As a result, a new compound 19a (SK053), which inhibits the activity of the Trx-TrxR system and exhibits antitumor activity, was obtained. Biologic analyses revealed that 19a inhibits induction of NF-kappa B and AP-1 and decreases H2O2 scavenging capacity in tumor cells. Altogether, we show that 19a is a novel potential antitumor peptidomimetic inhibitor that can be used as a starting compound for further optimization.

  DOI：

  10.1021/jm201359d
• 作为产物：
  描述：

  异氰基乙酸乙酯 、 2,4-二甲氧基苯甲胺 、 2-(溴甲基)丙烯酸 、 异戊醛 以 甲醇 为溶剂， 反应 21.0h， 以46%的产率得到{2-[(2-bromomethylacryloyl)-(2,4-dimethoxybenzyl)amino]-4-ethylpentanoylamino}acetic acid ethyl ester
  参考文献：
  名称：

  [EN] NOVEL ESTERS OF (ACYLOXYMETHYL)ACRYLAMIDE, A PHARMACEUTICAL COMPOSITION CONTAINING THEM, AND THEIR USE AS INHIBITORS OF THE THIOREDOXIN - THIOREDOXIN REDUCTASE SYSTEM
  [FR] NOUVEAUX ESTERS D'(ACYLOXYMÉTHYL)ACRYLAMIDE, COMPOSITION PHARMACEUTIQUE LES CONTENANT, ET LEUR UTILISATION EN TANT QU'INHIBITEURS DU SYSTÈME DE THIORÉDOXINE/THIORÉDOXINE RÉDUCTASE

  摘要：

  本发明的主题是新的（酰氧甲基）丙烯酰胺酯，其中包含它们的制药组合物以及它们在生产用于预防或治疗肿瘤性疾病和与细胞增殖增加有关的疾病的药物中的应用。

  公开号：

  WO2012050465A1

文献信息

• Novel Esters of (Acyloxymethyl)Acrylamide, a Pharmaceutical Composition Containing Them, and Their use as Inhibitors of the Thioredoxin - Thioredoxin Reductase System
  申请人：Ostaszewski Ryszard

  公开号：US20130317102A1

  公开（公告）日：2013-11-28

  The subject of the present invention are novel esters of (acyloxymethyl)acrylamide, a pharmaceutical composition containing them and their use in the production of drugs for the prophylaxis or treatment of oncogenic diseases and diseases connected with increased cell proliferation.

  本发明的主题是新颖的（酰氧甲基）丙烯酰胺酯，其中包含它们的药物组合物以及它们在生产预防或治疗肿瘤性疾病和与细胞增殖增加相关的疾病的药物中的使用。
• Esters of (acyloxymethyl)acrylamide, a pharmaceutical composition containing them, and their use as inhibitors of the thioredoxin—thioredoxin reductase system
  申请人：Ostaszewski Ryszard

  公开号：US09018255B2

  公开（公告）日：2015-04-28

  The subject of the present invention are novel esters of (acyloxymethyl)acrylamide, a pharmaceutical composition containing them and their use in the production of drugs for the prophylaxis or treatment of oncogenic diseases and diseases connected with increased cell proliferation.

  本发明的主题是新型的（酰氧甲基）丙烯酰胺酯，其中包含它们的制药组合物以及它们在预防或治疗肿瘤性疾病和与细胞增殖增加有关的疾病的药物生产中的应用。
• NOVEL ESTERS OF (ACYLOXYMETHYL)ACRYLAMIDE, A PHARMACEUTICAL COMPOSITION CONTAINING THEM, AND THEIR USE AS INHIBITORS OF THE THIOREDOXIN - THIOREDOXIN REDUCTASE SYSTEM
  申请人：Instytut Chemii Fizycznej Polskiej Akademii Nauk

  公开号：EP2627628A1

  公开（公告）日：2013-08-21
• US9018255B2
  申请人：——

  公开号：US9018255B2

  公开（公告）日：2015-04-28