N-(1H-indol-5-yl)-1-naphthalenesulfonamide | 528860-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(1H-indol-5-yl)-1-naphthalenesulfonamide
• 英文别名: N-[1H-indol-5-yl]naphthalene-1-sulphonamide；N-(1H-indol-5-yl)naphthalene-1-sulfonamide
• CAS: 528860-58-4
• 化学式: C₁₈H₁₄N₂O₂S
• 分子量: 322.387
• InChiKey: CFSUZYGWUBBKFG-UHFFFAOYSA-N

物化性质

• 沸点：
  586.7±42.0 °C(Predicted)
• 密度：
  1.432±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(1H-indol-5-yl)-1-naphthalenesulfonamide 在 lithium hydroxide monohydrate 、 水 、 sodium hydride 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 36.5h， 生成
  参考文献：
  名称：

  The discovery of indole full agonists of the neurotensin receptor 1 (NTSR1)

  摘要：

  Neurotensin (NT) is an endogenous tridecapeptide found in the central nervous system (CNS) and in peripheral tissues. Neurotensin exerts a wide range of physiological effects and it has been found to play a critical role in a number of human diseases, such as schizophrenia, Parkinson's disease and drug addiction. The discovery of small-molecule non-peptide neurotensin receptor (NTSR) modulators would represent an important breakthrough as such compounds could be used as pharmacological tools, to further decipher the cellular functions of neurotensin, and potentially as therapeutic agents to treat human disease. Herein, we report the identification of non-peptide low-micromolar neurotensin receptor 1 (NTSR1) full agonists, discovered through structural optimization of the known NTSR1 partial agonist 1. In vitro cellular screenings, based on an intracellular Ca(2+) mobilization assay, revealed our best hit molecule 8 (SR-12062) to have an EC50 of 2 μM at NTSR1 with full agonist behaviour (Emax=100%), showing a higher efficacy and ∼90-fold potency improvement compared to parent compound 1 (EC50=178 μM; Emax=17%).

  DOI：

  10.1016/j.bmcl.2014.06.033
• 作为产物：
  描述：

  5-氨基吲哚 、 1-萘磺酰氯 在 吡啶 作用下， 反应 2.0h， 以56%的产率得到N-(1H-indol-5-yl)-1-naphthalenesulfonamide
  参考文献：
  名称：

  N-（2-甲基-吲哚-1H-5-基）-1-萘磺酰胺：一种新型可逆的抗有丝分裂剂，可抑制癌细胞的运动

  摘要：

  合成了一系列含有磺酰胺骨架的化合物，并筛选了它们对人癌细胞系代表细胞的体外抗癌活性，从而鉴定出N-（2-甲基-1H-吲哚-5-基）-1 -萘磺酸酰胺（8e）作为化合物在整个面板上均显示出显着的活性，IC50值在纳摩尔至低微摩尔范围内。细胞周期分布分析显示8e促进了严重的G2 / M阻滞，随后在8e处理的细胞中检测到与衰老相关的β-半乳糖苷酶（SA-β-gal），表明细胞发生了衰老。延长的8e治疗还导致凋亡的发生，与Caspase 3/7活性增加的检测有关。尽管γ-H2A.X水平升高，但DNA双链断裂的公认读数，用8e进行的体外DNA结合研究不支持与DNA的相互作用。与此相符，8e无法激活细胞DNA损伤检查点。重要的是，微管蛋白染色显示8e促进了微管的严重混乱，并且在8e处理的细胞中未检测到有丝分裂纺锤体的形成。因此，8e在体外以剂量依赖的方式抑制微管蛋白的聚合，并且还能够强有力地抑制癌细胞

  DOI：

  10.1016/j.bcp.2016.06.016

文献信息

• [EN] ACTIVE SUBSTANCE COMBINATION COMPRISING A COMPOUND WITH NPY RECEPTOR AFFINITY AND A COMPOUND WITH 5-HT6 RECEPTOR AFFINITY<br/>[FR] COMBINAISON DE SUBSTANCES ACTIVES COMPORTANT UN COMPOSE A AFFINITE DE RECEPTEUR NPY ET UN COMPOSE A AFFINITE DE RECEPTEUR 5-HT6
  申请人：ESTEVE LABOR DR

  公开号：WO2005014000A1

  公开（公告）日：2005-02-17

  The present invention relates to an active substance combination comprising at least one compound with neuropeptide Y-receptor affinity and at least one compound with 5-HT6 receptor affinity, a medicament comprising said active substance combination, and the use of said active substance combination for the manufacture of a medicament.

  本发明涉及一种活性物质组合，包括至少一种具有神经肽Y受体亲和力的化合物和至少一种具有5-HT6受体亲和力的化合物，以及包含所述活性物质组合的药物和利用该活性物质组合制造药物的用途。
• Derivatives of sulphonamides, their preparation and use as medicaments
  申请人：——

  公开号：US20030191124A1

  公开（公告）日：2003-10-09

  The present invention relates to new derivatives of sulphonamides, with the general formula (I), as well as to their physiologically acceptable salts, the processes for their preparation, their application as medicaments in human and/or veterinary therapy and the pharmaceutical compositions that contain them 1

  本发明涉及磺胺类的新衍生物，其通式为（I），以及其生理上可接受的盐、其制备过程、其在人类和/或兽医疗法中作为药物的应用和含有它们的制药组合物。
• Use of sulphonamide derivatives for the manufacture of a medicament for the prophylaxis and/or treatment of disorders of food ingestion
  申请人：Vidal Merce Ramon

  公开号：US20050065202A1

  公开（公告）日：2005-03-24

  The present invention relates to the use of sulphonamide derivatives of general formula (I), optionally in form of one of their stereoisomers, preferably enantiomers or diastereomers, their racemates or in form of a mixture of at least two of their stereoisomers, preferably enantiomers or diastereomers, in any mixing ratio, or corresponding physiologically acceptable salts or corresponding solvates, for the manufacture of a medicament for the prophylaxis and/or treatment of disorders of food ingestion.

  本发明涉及通式（I）的磺酰胺衍生物的使用，其可以是其立体异构体之一，优选是对映异构体或顺反异构体，它们的外消旋体或至少两个立体异构体的混合物，优选是对映异构体或顺反异构体，其混合比例可以任意，或相应的生理上可接受的盐或相应的溶剂化物，用于制造用于预防和/或治疗进食障碍的药物。
• [EN] USE OF SULPHONAMIDE DERIVATIVES FOR THE MANUFACTURE OF A MEDICAMENT FOR THE PROPHYLAXIS AND/OR TREATMENT OF DISORDERS OF FOOD INGESTION<br/>[FR] UTILISATION DE DERIVES SULFAMIDES POUR LA FABRICATION D'UN MEDICAMENT POUR LA PROPHYLAXIE ET/OU LE TRAITEMENT DE TROUBLES D'INGESTION DES ALIMENTS
  申请人：ESTEVE LABOR DR

  公开号：WO2004098588A1

  公开（公告）日：2004-11-18

  The present invention relates to the use of sulphonamide derivatives of general formula (1), optionally in form of one of their stereoisomers, preferably enantiomers or diastereomers, their racemates or in form of a mixture of at least two of their stereoisomers, preferably enantiomers or diastereomers, in any mixing ratio, or corresponding physiologically acceptable salts or corresponding solvates, for the manufacture of a medicament for the prophylaxis and/or treatment of disorders of food ingestion.

  本发明涉及使用一般式（1）的磺胺类衍生物，可选地为它们的立体异构体之一，优选为对映异构体或非对映异构体，它们的外消旋体或至少两个立体异构体的混合物，优选为对映异构体或非对映异构体，其混合比例任意，或相应的生理上可接受的盐或相应的溶剂化物，用于制造用于预防和/或治疗食物摄入障碍的药物。
• Active substance combination comprising a compound with npy receptor affinity and a compound with 5-ht6 receptor affinity
  申请人：Torrens Jover Antoni

  公开号：US20070009597A1

  公开（公告）日：2007-01-11

  The present invention relates to an active substance combination comprising at least one compound with neuropeptide Y-receptor affinity, preferably neuropeptide Y5-receptor affinity, and at least one compound with 5-HT 6 receptor affinity, a medicament comprising said active substance combination, and the use of said active substance combination for the manufacture of a medicament.

  本发明涉及一种活性物质组合，包括至少一种具有神经肽Y受体亲和力的化合物，优选为神经肽Y5受体亲和力，以及至少一种具有5-HT6受体亲和力的化合物，一种包含该活性物质组合的药物，以及使用该活性物质组合制造药物。