4-chloro-N-ethyl-3-nitrobenzenesulfonamide | 43041-67-4

• 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-chloro-N-ethyl-3-nitrobenzenesulfonamide
• 英文别名: 4-chloro-3-nitro-benzenesulfonic acid ethylamide；4-Chlor-3-nitro-benzolsulfonsaeure-aethylamid；4-chloro-N-ethyl-3-nitro-benzenesulfonamide；1-Chlor-2-nitro-benzol-4-sulfonsaeure-aethylamid
• CAS: 43041-67-4
• 化学式: C₈H₉ClN₂O₄S
• mdl: MFCD11185145
• 分子量: 264.689
• InChiKey: VUBCPDLPDLXFOL-UHFFFAOYSA-N

物化性质

• 沸点：
  401.3±55.0 °C(Predicted)
• 密度：
  1.467±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-chloro-N-ethyl-3-nitrobenzenesulfonamide 在 氢气 、 palladium(II) hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 34.0h， 生成 4-(adamantan-2-ylamino)-3-amino-N-ethylbenzenesulfonamide
  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
• 作为产物：
  描述：

  4-氯-3-硝基苯磺酰氯 、 乙胺盐酸盐 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以72%的产率得到4-chloro-N-ethyl-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

• [DE] ((11-OXO-10,11-DIHYDRODIBENZO [B, F] [1, 4] OXAZEPIN-1-YL)OXY) ESSIGSÄURE-DERIVATE UND VERWANDTE VERBINDUNGEN ALS HERZ-KREISLAUFMITTEL ZUR BEHANDLUNG VON ATHEROSCLEROSE<br/>[EN] ((11-OXO-10,11-DIHYDRODIBENZO [B, F] [1, 4] OXAZEPIN-1-YL)OXY) ACETIC ACID DERIVATIVES AND RELATED COMPOUNDS AS CARDIOVASCULAR PREPARATIONS USED TO TREAT ARTERIOLOSCLEROSIS<br/>[FR] DERIVES D'ACIDE ((11-OXO-10,11-DIHYDRODIBENZO[B, F][1, 4]OXAZEPIN-1-YL)OXY) ACETIQUE ET COMPOSES APPARENTES COMME AGENTS CARDIOVASCULAIRES POUR LE TRAITEMENT DE L'ATHEROSCLEROSE
  申请人：BAYER HEALTHCARE AG

  公开号：WO2005072741A1

  公开（公告）日：2005-08-11

  Die vorliegende Erfindung betrifft Dibenzoxazepine und Verfahren zu ihrer Herstellung, ihre Verwendung zur Behandlung und/oder Prophylaxe von Krankheiten sowie ihre Verwendung zur Herstellung von Arzneimitteln zur Behandlung und/oder Prophylaxe von Krankheiten, insbesondere von Herz-Kreislauf-Erkrankungen, zB. von Atherosklerose, und Krebserkrankungen: Formel (I), worin R2 C1-C6-Alkyl bedeutet, wobei Alkyl substituiert sein kann mit 1 oder 2 Substituenten, wobei die Substituenten unabhängig voneinander ausgewählt werden aus der Gruppe bestehend aus Halogen, Hydroxy, Oxo, C1-C6-Alkoxy, Hydroxycarbonyl, C1-C6-Alkoxycarbonyl, Aminocarbonyl und C1-C6-Alkylaminocarbonyl, R3 -O-CH2CO2H oder -O-(CH2)2CO2H bedeutet, R5 5- bis 10-gliedriges Heteroaryl, -SO2-R6 oder -NR7(C=O)R8 bedeutet, wobei Heteroaryl substituiert sein kann mit 1, 2 oder 3 Substituenten, wobei die Substi­tuenten unabhängig voneinander ausgewählt werden aus der Gruppe bestehend aus Halogen, Trifluormethyl, Trifluormethoxy, Cyano, Nitro, Amino, C1-C6 Alkylamino, Hydroxy, C1-C6-Alkyl, C1-C6-AIkoxy, Hydroxycarbonyl, C1-C6-Alkoxycarbonyl, Amino­carbonyl, C1-C6-Alkylaminocarbonyl, C6-C10-Aryl und C3-C8-Cycloalkyl, die anderen Substituenten sind in den Ansprüchen definiert.

  本发明涉及二苯并噁唑和其制备方法，其用于治疗和/或预防疾病以及用于制备用于治疗和/或预防疾病的药物，特别是心血管疾病，例如动脉粥样硬化，和癌症的用途：式（I），其中R2为C1-C6烷基，其中烷基可以被1或2个取代基取代，取代基独立地选择自卤素、羟基、羰基、C1-C6烷氧基、羟基羰基、C1-C6烷氧羰基、氨基羰基和C1-C6烷基氨基羰基的群组，R3为-O-CH2CO2H或-O-(CH2)2CO2H，R5为5-至10-成员的杂环芳基，-SO2-R6或-NR7(C=O)R8，其中杂环芳基可以被1、2或3个取代基取代，取代基独立地选择自卤素、三氟甲基、三氟甲氧基、氰基、硝基、氨基、C1-C6烷基氨基、羟基、C1-C6烷基、C1-C6烷氧基、羟基羰基、C1-C6烷氧羰基、氨基羰基、C1-C6烷基氨基羰基、C6-C10芳基和C3-C8环烷基，其他取代基在权利要求中定义。
• [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。
• Nitrodiphenylamine compounds containing a sulfamyl group
  申请人：EASTMAN KODAK CO

  公开号：US02466010A1

  公开（公告）日：1949-04-05
• Bicyclic compound containing a diphenylamine nucleus
  申请人：EASTMAN KODAK CO

  公开号：US02422029A1

  公开（公告）日：1947-06-10
• Sulphonamido azo pyrazolones
  申请人：EASTMAN KODAK CO

  公开号：US02391180A1

  公开（公告）日：1945-12-18