4-chloro-N-(2-morpholinoethyl)-3-nitrobenzenesulfonamide | 743452-14-4

• 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-(2-morpholinoethyl)-3-nitrobenzenesulfonamide
• 英文别名: 4-chloro-N-(2-morpholin-4-ylethyl)-3-nitrobenzenesulfonamide
• CAS: 743452-14-4
• 化学式: C₁₂H₁₆ClN₃O₅S
• mdl: MFCD01269351
• 分子量: 349.795
• InChiKey: IUHPWOOFODCLOQ-UHFFFAOYSA-N

物化性质

• 溶解度：
  >52.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-chloro-N-(2-morpholinoethyl)-3-nitrobenzenesulfonamide 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 3-Amino-4-benzylamino-N-(2-morpholin-4-yl-ethyl)-benzenesulfonamide
  参考文献：
  名称：

  苯并咪唑衍生物作为新型非肽促黄体激素释放激素（LHRH）拮抗剂。第1部分：苯并咪唑-5-磺酰胺。

  摘要：

  一类新的苯并咪唑-5-磺酰胺已被确定为非肽黄体生成素释放激素（LHRH）拮抗剂。提出了初始的结构-活性关系，导致化合物19和28对人和大鼠的受体具有亚微摩尔的双重功能活性。

  DOI：

  10.1016/j.bmcl.2004.10.089
• 作为产物：
  描述：

  N-(2-氨基乙基)吗啉 、 4-氯-3-硝基苯磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到4-chloro-N-(2-morpholinoethyl)-3-nitrobenzenesulfonamide
  参考文献：
  名称：

  Discovery of Novel, Drug-Like Ferroptosis Inhibitors with in Vivo Efficacy

  摘要：

  Ferroptosis is an iron-catalyzed, nonapoptotic form of regulated necrosis that results in oxidative lipid damage in cell membranes that can be inhibited by the radical-trapping antioxidant Ferrostatin-1 (Fer-1). Novel inhibitors derived from the Fer-1 scaffold inhibited ferroptosis potently but suffered from solubility issues. In this paper, we report the synthesis of a more stable and readily soluble series of Fer-1 analogues that potently inhibit ferroptosis. The most promising compounds (37, 38, and 39) showed an improved protection compared to Fer-1 against multiorgan injury in mice. No toxicity was observed in mice after daily injection of 39 (UAMC-3203) for 4 weeks. UAMC-3203 inserts rapidly in a phospholipid bilayer in silico, which aligns with the current understanding of the mechanism of action of these compounds. In conclusion, these analogues have superior properties compared to Fer-1, show in vivo efficacy, and represent novel lead compounds with therapeutic potential in relevant ferroptosis-driven disease models.

  DOI：

  10.1021/acs.jmedchem.8b01299

文献信息

• [EN] 3-(BENZYLAMINO)-4-(CYCLOHEXYLAMINO)-N-(2-(PIPERAZIN-1-YL)ETHYL)BENZENESULFONAMIDE DERIVATIVES AND RELATED FERROSTATIN-1 ANALOGUES AS CELL DEATH INHIBITORS FOR TREATING E.G. STROKE<br/>[FR] DÉRIVÉS DE 3-(BENZYLAMINO)-4-(CYCLOHEXYLAMINO)-N-(2-(PIPÉRAZIN-1-YL)ÉTHYL)BENZÈNESULFONAMIDE ET ANALOGUES DE FERROSTATINE-1 ASSOCIÉS EN TANT QU'INHIBITEURS DE MORT CELLULAIRE POUR LE TRAITEMENT, PAR EXEMPLE, D'UN ACCIDENT VASCULAIRE CÉRÉBRAL
  申请人：VIB VZW

  公开号：WO2019154795A1

  公开（公告）日：2019-08-15

  The present invention relates to 3-(benzylamino)-4-(cyclohexylamino)-N-(2-(piperazin-1-yl)ethyl)benzenesulfonamide derivatives and related ferrostatin-1 (Fer-1) analogues as cell death inhibitors by inhibition of ferroptosis and/or oxytosis for the treatment of stroke, myocardial infarction, diabetes, sepsis, the prevention of transplant rejection, neurodegenerative diseases including Alzheimer's disease, Parkinson's disease, amyotrophic lateral sclerosis, multiple sclerosis, Huntington's disease, dementia with Lewy bodies and Friedreich's ataxia. The present invention further relates to pharmaceutical compositions of these compounds and discloses methods for making the compounds and the corresponding intermediate.

  本发明涉及3-(苄基氨基)-4-(环己基氨基)-N-(2-(哌嗪-1-基)乙基)苯磺酰胺衍生物及相关的铁死亡素-1（Fer-1）类似物，作为抑制铁死亡和/或氧化死亡的细胞死亡抑制剂，用于治疗中风、心肌梗死、糖尿病、败血症、预防移植排斥、神经退行性疾病，包括阿尔茨海默病、帕金森病、肌萎缩性侧索硬化、多发性硬化、亨廷顿病、带有莱维小体的痴呆症和弗里德雷希共济失调症。本发明还涉及这些化合物的制药组合物，并公开了制备这些化合物及其相应中间体的方法。
• 3-(benzylamino)-4-(cyclohexylamino)-n-(2-(piperazin-1-yl)ethyl)benzenesulfonamide derivatives and related ferrostatin-1 analogues as cell death inhibitors for treating e.g. stroke
  申请人：VIB VZW

  公开号：US11339124B2

  公开（公告）日：2022-05-24

  The present invention relates to 3-(benzylamino)-4-(cyclohexylamino)-N-(2-(piperazin-1-yl)ethyl)benzenesulfonamide derivatives and related ferrostatin-1 (Fer-1) analogues as cell death inhibitors by inhibition of ferroptosis and/or oxytosis for the treatment of stroke, myocardial infarction, diabetes, sepsis, the prevention of transplant rejection, neurodegenerative diseases including Alzheimer's disease, Parkinson's disease, amyotrophic lateral sclerosis, multiple sclerosis, Huntington's disease, dementia with Lewy bodies and Friedreich's ataxia. The present invention further relates to pharmaceutical compositions of these compounds and discloses methods for making the compounds and the corresponding intermediate.

  本发明涉及 3-(苄基氨基)-4-(环己基氨基)-N-(2-(哌嗪-1-基)乙基)苯磺酰胺衍生物和相关的铁前列素-1（Fer-1）类似物，它们通过抑制铁氧化和/或氧氧化作用而成为细胞死亡抑制剂，用于治疗中风、心肌梗塞、糖尿病、败血症、预防移植排斥反应、神经退行性疾病（包括阿尔茨海默病、帕金森病、肌萎缩侧索硬化症）、心肌梗塞、糖尿病、败血症、预防移植排斥反应、神经退行性疾病，包括阿尔茨海默病、帕金森病、肌萎缩性脊髓侧索硬化症、多发性硬化症、亨廷顿氏病、路易体痴呆症和弗里德里希共济失调症。本发明进一步涉及这些化合物的药物组合物，并公开了制造这些化合物和相应中间体的方法。
• EP3749645A1
  申请人：——

  公开号：EP3749645A1

  公开（公告）日：2020-12-16
• 3-(BENZYLAMINO)-4-(CYCLOHEXYLAMINO)-N-(2-(PIPERAZIN-1-YL)ETHYL)BENZENESULFONAMIDE DERIVATIVES AND RELATED FERROSTATIN-1 ANALOGUES AS CELL DEATH INHIBITORS FOR TREATING E.G. STROKE
  申请人：VIB VZW

  公开号：US20210094909A1

  公开（公告）日：2021-04-01

  The present invention relates to 3-(benzylamino)-4-(cyclohexylamino)-N-(2-(piperazin-1-yl)ethyl)benzenesulfonamide derivatives and related ferrostatin-1 (Fer-1) analogues as cell death inhibitors by inhibition of ferroptosis and/or oxytosis for the treatment of stroke, myocardial infarction, diabetes, sepsis, the prevention of transplant rejection, neurodegenerative diseases including Alzheimer's disease, Parkinson's disease, amyotrophic lateral sclerosis, multiple sclerosis, Huntington's disease, dementia with Lewy bodies and Friedreich's ataxia. The present invention further relates to pharmaceutical compositions of these compounds and discloses methods for making the compounds and the corresponding intermediate.
• Benzimidazole derivatives as novel nonpeptide luteinizing hormone-releasing hormone (LHRH) antagonists. Part 1: Benzimidazole-5-sulfonamides
  作者：Kentaro Hashimoto、Miyuki Tatsuta、Mikayo Kataoka、Kayo Yasoshima、Yuka Shogase、Makoto Shimazaki、Takeshi Yura、Yingfu Li、Noriyuki Yamamoto、Jang B. Gupta、Klaus Urbahns

  DOI：10.1016/j.bmcl.2004.10.089

  日期：2005.2

  A new class of benzimidazole-5-sulfonamides has been identified as nonpeptide luteinizing hormone-releasing hormone (LHRH) antagonists. Initial structure-activity relationships are presented resulting in compounds 19 and 28 with submicromolar dual functional activity on human and rat receptors.

  一类新的苯并咪唑-5-磺酰胺已被确定为非肽黄体生成素释放激素（LHRH）拮抗剂。提出了初始的结构-活性关系，导致化合物19和28对人和大鼠的受体具有亚微摩尔的双重功能活性。