N-butyl-2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-butyl-2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetamide
• 英文别名: N-butyl-2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetamide
• 化学式: C₁₇H₂₁Cl₂NO₃
• 分子量: 358.265
• InChiKey: GHISKXRDUBGTPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  利尿酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 正丁胺 、 N,N'-二环己基碳二亚胺 作用下， 以65 %的产率得到N-butyl-2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetamide
  参考文献：
  名称：

  ETHACRYNIC ACID DERIVATIVES AS INHIBITORS OF MPRO PROTEASE AND SARS-COV-2 REPLICATION

  摘要：

  A novel compound of formulae (I) or (II), to the use thereof as a drug, particularly for the treatment of SARS-COV-2, for the treatment of COVID-19 disease and any diseases related to beta-coronaviruses, and for the in vitro application thereof in order to study the interaction with Mpro protease.

  公开号：

  US20240287003A1

文献信息

• Combining a Solution-Phase Derived Library with In-Situ Cellular Bioassay: Prompt Screening of Amide-Forming Minilibraries Using MTT Assay
  作者：Li-Wu Chiang、Kai Pei、Shao-Wei Chen、Ho-Lien Huang、Kun-Ju Lin、Tzu-Chen Yen、Chung-Shan Yu

  DOI：10.1248/cpb.57.714

  日期：——

  We constructed a minilibrary using a solution-phase synthesis through coupling of three core amino compounds (5′-amino-5′-deoxy uridine, 5′-amino-2′,5′-di-deoxy arabinosyl uridine, and butan-1-amine) with 30 carboxylic acids via amide bond formation. The simplified structural core compound butan-1-amine was selectively coupled with 9 carboxylic acids as control. 3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide assay of the crude mixtures showed that analogues derived from fenbufen, butylfenbufen C15; ethacrynic acid, butyl ethacrynic amide C18; and sphingosines, Sph-1, Sph-2 and U27 had an increased cytotoxicity against MCF-7 cells as well as A549 cells. Structural elucidation with molecular docking suggested that cytotoxicity of these compounds is mainly due to the inhibition of enzymes regulating cellular apoptosis.

  我们通过三种核心氨基酸化合物（5'-氨基-5'-脱氧尿苷、5'-氨基-2',5'-二脱氧阿糖尿苷和丁胺）与30种羧酸通过酰胺键形成，采用溶液相合成方法构建了一个微型库。简化的结构核心化合物丁胺选择性地与9种羧酸进行了耦合作为对照。对粗混合物的3-(4,5-二甲基-2-噻唑基)-2,5-二苯基-2H-四唑溴盐检测显示，来自非诺洛芬、丁基非诺洛芬C15；依他尼酸、丁基依他尼酸酰胺C18；以及鞘氨醇、Sph-1、Sph-2和U27的类似物对MCF-7细胞以及A549细胞表现出增强的细胞毒性。通过分子对接进行结构阐明表明，这些化合物的细胞毒性主要由于抑制调控细胞凋亡的酶。
• Synthesis and Evaluation of Non-peptidic Cysteine Protease Inhibitors of P. falciparum Derived from Etacrynic Acid
  作者：Marie-Adrienne Dude、Ulrich Kaeppler、Monika Herb、Markus Schiller、Franziska Schulz、Birgit Vedder、Saskia Heppner、Gabriele Pradel、Jiri Gut、Philip Rosenthal、Tanja Schirmeister、Matthias Leippe、Christoph Gelhaus

  DOI：10.3390/molecules14010019

  日期：——

  A series of etacrynic acid derivatives was synthesized and screened for their in vitro activity against Plasmodium falciparum, as well as their activity against recombinantly expressed falcipain-2 and -3. The two most active compounds of the series displayed IC50 values of 9.0 and 18.8 μM against Plasmodia.

  一系列依他尼酸衍生物被合成并筛选其对恶性疟原虫的体外活性，以及它们对重组表达的法西平-2和法西平-3的活性。该系列中活性最强的两种化合物对疟原虫的IC50值分别为9.0和18.8 μM。
• Method and precursor for production of no-carrier-added N-(4-[18F] fluorobutyl)-Ethacrynic amide
  申请人：Yu Chung-Shan

  公开号：US20110077430A1

  公开（公告）日：2011-03-31

  The present invention is related to a precursor for no-carrier-added fluorine-18 labeled ethacrynic acid, N-(4-[ 18 F]fluorobutyl)-Ethacrynic amide([ 18 F]FBuEA) and the preparation method for HPLC non-radioactive standards. Its chemical structure is shown in the following: In the precursor, R 1 represents a protective group for the amide functional group; R 2 represents leaving group; or R 1 represents carboxyl group, R 2 represents p-tosyloxy, methane sulfonyloxy group or trifluoromethane sulfonyloxy group or bromine (Br). For the HPLC non-radioactive standards, R 1 represents a protective group for the amide functional group and hydrogen, R 2 represents fluorine.

  本发明涉及一种用于无载体添加氟-18标记的依他克酸前体，N-(4-[18F]氟丁基)-依他克酰胺([18F]FBuEA)以及HPLC非放射性标准的制备方法。其化学结构如下所示：在前体中，R1代表酰胺官能团的保护基；R2代表脱离基团；或者R1代表羧基，R2代表对甲苯磺酰氧基、甲磺酰氧基或三氟甲磺酰氧基或溴（Br）。对于HPLC非放射性标准，R1代表酰胺官能团的保护基和氢，R2代表氟。
• METHOD OF PREPARING ETHACRYNIC AMIDE DERIVATIVES AND APPLICATION THEREOF
  申请人：National Tsing Hua University

  公开号：US20130156701A1

  公开（公告）日：2013-06-20

  The present invention provides a method for preparing [ 18 F]—N-(4-fluorobutyl)ethacrynic amide which is prepared from radiofluorination and deprotection of the precursor tosylate N-Boc-N-[4-(toluenesulfonyloxy)-butyl)ethacrynic amide], obtained from ethacrynic acid via 6-step synthesis in 39% yield, in a radiochemical yield of 44%, aspecific activity of 48 GBq/μmol and radiochemical purity of 98%. The present invention further provides a composition for positron emission tomography (PET) of an animal models of a tumor liver or a liver disease, comprising [ 18 F]—N-(4-fluorobutyl)ethacrynic amide and a pharmaceutically acceptable carrier.

  本发明提供了一种制备[18F]-N-(4-氟丁基)乙丙烯酰胺的方法，该方法是通过对前体对甲苯磺酸酯N-Boc-N-[4-(甲苯磺酰氧基)-丁基）乙丙烯酰胺进行放射氟化和脱保护而制备的，该前体是从乙丙烯酸经过6步合成得到，收率为39%，放射化学收率为44%，比活度为48GBq/μmol，放射化学纯度为98%。本发明还提供了一种用于肿瘤肝脏或肝脏疾病动物模型的正电子发射断层扫描（PET）的组合物，包括[18F]-N-(4-氟丁基)乙丙烯酰胺和一种药用可接受载体。
• CONSTRUCTION AND SCREENING OF SOLUTION-PHASE DERIVED LIBRARY OF FENBUFEN AND ETHACRYNIC ACID
  申请人：Yu Chung-Shan

  公开号：US20110306668A1

  公开（公告）日：2011-12-15

  A process for synthesizing and screening solution phase derived libraries of fenbufen and ethacrynic acid is provided in the present invention. Compounds in the present invention having cytotoxicities are useful for a variety of therapeutic applications.

  本发明提供了一种合成和筛选溶液相衍生的芬布芬和依他克酸库的过程。本发明中具有细胞毒性的化合物对多种治疗应用是有用的。