4-(cyclohexylamino)-N-methyl-3-nitrobenzenesulfonamide

• 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: 4-(cyclohexylamino)-N-methyl-3-nitrobenzenesulfonamide
• 化学式: C₁₃H₁₉N₃O₄S
• 分子量: 313.378
• InChiKey: GBIJEUWVKFCJBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(cyclohexylamino)-N-methyl-3-nitrobenzenesulfonamide 在 乙醇 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(2-(cyclohexylamino)-5-(N-methylsulfamoyl)phenyl)acrylamide
  参考文献：
  名称：

  [EN] TRANSCRIPTIONAL ENHANCED ASSOCIATE DOMAIN (TEAD) TRANSCRIPTION FACTOR INHIBITORS AND USES THEREOF
  [FR] INHIBITEURS DU FACTEUR DE TRANSCRIPTION À DOMAINE ASSOCIÉ TRANSCRIPTIONNEL AMÉLIORÉ (TEAD) ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2021133896A8
• 作为产物：
  描述：

  4-氯-3-硝基苯磺酰氯 在 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 4-(cyclohexylamino)-N-methyl-3-nitrobenzenesulfonamide
  参考文献：
  名称：

  Novel Ferroptosis Inhibitors with Improved Potency and ADME Properties

  摘要：

  Ferroptosis is a nonapoptotic, iron-catalyzed form of regulated necrosis that is critically dependent on glutathione peroxidase 4 (GPX4). It has been shown to contribute to liver and kidney ischemia reperfusion injury in mice. A chemical inhibitor discovered by high throughput screening displayed inhibition of ferroptosis with nanomolar activity and was dubbed ferrostatin-1 (fer-1). Ferrostatins inhibit oxidative lipid damage, but suffer from inherent stability problems due to the presence of an ester moiety. This limits the application of these molecules in vivo, due to rapid hydrolysis of the ester into the inactive carboxylic acid. Previous studies highlighted the importance of the ethyl ester and suggested steric modifications of the ester for generating improved molecules. In this study, we report the synthesis of novel ferroptosis inhibitors containing amide and sulfonamide moieties with improved stability, single digit nanomolar antiferroptotic activity, and good ADME properties suitable for application in in vivo disease models.

  DOI：

  10.1021/acs.jmedchem.5b01641

文献信息

• [EN] 3,4-DIAMINOBENZENESULFONAMIDE DERIVATIVES FOR INHIBITING CELL DEATH<br/>[FR] DÉRIVÉS DE 3,4-DIAMINOBENZÈNESULFONAMIDE POUR INHIBER LA MORT CELLULAIRE
  申请人：VIB VZW

  公开号：WO2016075330A1

  公开（公告）日：2016-05-19

  The present invention relates to a novel class of compounds having the structure of formula (I) and pharmaceutical compositions comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof. These compounds inhibit or reduce the non-apoptotic cell death forms ferroptosis and/or oxytosis rendering them useful for the treatment of various conditions disclosed herein.

  本发明涉及一种新型化合物类，其结构式为(I)，以及包含式(I)化合物或其药学上可接受的盐的制药组合物。这些化合物抑制或减少非凋亡细胞死亡形式的铁死亡和/或氧死亡，因此可用于治疗本文所披露的各种疾病。
• 3,4-DIAMINOBENZENESULFONAMIDE DERIVATIVES FOR INHIBITING CELL DEATH
  申请人：VIB vzw

  公开号：EP3218357B1

  公开（公告）日：2020-04-29
• TRANSCRIPTIONAL ENHANCED ASSOCIATE DOMAIN (TEAD) TRANSCRIPTION FACTOR INHIBITORS AND USES THEREOF
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：EP4081202A1

  公开（公告）日：2022-11-02
• US9862678B2
  申请人：——

  公开号：US9862678B2

  公开（公告）日：2018-01-09
• [EN] TRANSCRIPTIONAL ENHANCED ASSOCIATE DOMAN (TEAD) TRANSCRIPTION FACTOR INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DU FACTEUR DE TRANSCRIPTION À DOMAINE ASSOCIÉ TRANSCRIPTIONNEL AMÉLIORÉ (TEAD) ET LEURS UTILISATIONS
  申请人：[en]DANA-FARBER CANCER INSTITUTE, INC.

  公开号：WO2021133896A1

  公开（公告）日：2021-07-01

  Provided herein are compounds of (I-A), (I-B), or (II), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, and prodrugs thereof. Also provided are methods, uses, and kits involving the inventive compounds and pharmaceutical compositions thereof for treating and/or preventing diseases (e.g., proliferative diseases (e.g., cancers), inflammatory diseases (e.g., fibrosis), autoimmune diseases (e.g., sclerosis)) in a subject. Provided are methods of inhibiting the activity of a transcription factor (e.g., TEAD, such as TEAD1, TEAD2, TEAD3, TEAD4) and/or inhibiting the transcription of a gene (e.g., a gene controlled or regulated by a transcription factor(e.g., TEAD)) in a subject.