N-(4-羟基丁基)-N-甲基-4-苯基苯磺酰胺 | 871113-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-羟基丁基)-N-甲基-4-苯基苯磺酰胺
• 英文名称: biphenyl-4-sulfonic acid-(4-hydroxybutyl)-methyl-amide
• 英文别名: biphenyl-4-sulfonic acid-(4-hydroxybutyl)methylamide；N-(4-hydroxybutyl)-N-methyl-4-phenylbenzenesulfonamide
• CAS: 871113-53-0
• 化学式: C₁₇H₂₁NO₃S
• 分子量: 319.425
• InChiKey: VCPPBHQUHWBXCX-UHFFFAOYSA-N

物化性质

• 熔点：
  89-90 °C
• 沸点：
  493.2±55.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对联苯磺酰氯 在 吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 N-(4-羟基丁基)-N-甲基-4-苯基苯磺酰胺
  参考文献：
  名称：

  Development and Characterization of Biphenylsulfonamides as Novel Inhibitors of Bone Resorption

  摘要：

  Increased osteoclastic bone resorption plays a central role in the pathogenesis of many bone diseases, and osteoclast inhibitors are the most widely used treatments for these diseases. We have identified and characterized a series of novel biphenylsulfonamide derivatives that have potent inhibitory effects on osteoclastic bone resorption in vitro and that prevent ovariectomy-induced bone loss in vivo. A number of aromatic substituted derivatives were prepared and a QSAR model was generated, which allowed accurate prediction of compound potency. Using this model, we have prepared compounds able to inhibit osteoclast formation and bone resorption in vitro at concentrations in the nanomolar range. One such compound, 55 (ABD295) (Greig, I. R.; Mohamed, A. I.; Ralston, S. H.; van't Hof, R. J. Alkyl Aryl Sulfonamides as Therapeutic Agents for the Treatment of Bone Conditions. GB Patent WO2005118528, 2005), fully reversed ovariectomy-induced bone loss in mice at a dose of 5 (mg/kg)/day. In conclusion, biphenylsulfonamides like 55 form a new class of potent antiresorptive agents with possible therapeutic use in diseases characterized by increased bone resorption.

  DOI：

  10.1021/jm051236m
• 作为试剂：
  描述：

  N-(4-羟基丁基)-4-苯基苯磺酰胺 、 碘甲烷 、 、 水 在 N-(4-羟基丁基)-N-甲基-4-苯基苯磺酰胺 、 乙醚 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以to give the title compound as a white solid (80%)的产率得到N-(4-羟基丁基)-N-甲基-4-苯基苯磺酰胺
  参考文献：
  名称：

  Aryl Alkyl Sulfonamides As Therapeutic Agents For The Treatment Of Bone Conditions

  摘要：

  本发明涉及某些芳基烷基磺酰胺及其衍生物，其中，它们抑制破骨细胞的存活、形成和/或活性；和/或抑制骨吸收，更具体地说，是式子的化合物： 其中：Ar1独立地是C5-20芳基（例如，联苯、菲、芴或咔唑基，最好是联苯），并且可以选择性地被取代；RN独立地是-H、酰基、C5-20芳基-C1-7烷基、C3-20杂环基或C1-7烷基，并且可以选择性地被取代；Ralk是C2-10烷基链，可以选择性地被取代；Q独立地是-H或具有1-30个由碳、氮、氧、硫、磷、氟、氯、溴和碘选择的有机基团（例如，氧型基团，胺型基团等）；以及其药学上可接受的盐、溶剂化合物、酰胺、酯、醚、化学保护形式和前药。本发明还涉及包含这样的化合物的制药组合物，以及在体外和体内使用这样的化合物和组合物来抑制破骨细胞的存活、形成和/或活性，并抑制由破骨细胞介导和/或通过骨吸收表征的骨疾病的治疗，例如骨质疏松症、类风湿性关节炎、与癌症相关的骨疾病、帕吉特病等；和/或用于治疗与炎症或免疫系统激活有关的疾病。

  公开号：

  US20080119555A1

文献信息

• Aryl alkyl sulfonamides as therapeutic agents for the treatment of bone conditions
  申请人：The University Court of the University of Aberdeen

  公开号：US07964643B2

  公开（公告）日：2011-06-21

  The present invention pertains to compounds of the following formula (wherein RP, r, q, RN, Ralk, and Q are as defined herein) and compositions comprising those compounds. The compounds may be used to inhibit osteoclast survival, formation, and/or activity; to inhibit conditions mediated by osteoclasts and/or characterised by bone resorption; in the treatment of bone disorders such as osteoporosis, rheumatoid arthritis, cancer associated bone disease, Paget's disease; and/or in the treatment of conditions associated with inflammation or activation of the immune system.

  本发明涉及以下式子的化合物（其中RP、r、q、RN、Ralk和Q的定义如下）以及含有这些化合物的组合物。这些化合物可以用于抑制破骨细胞的存活、形成和/或活性；抑制由破骨细胞介导的和/或以骨吸收为特征的疾病；用于治疗骨疾病，如骨质疏松、类风湿性关节炎、与癌症相关的骨病和Paget病；以及用于治疗与炎症或免疫系统激活相关的疾病。
• [EN] ARYL ALKYL SULFONAMIDES AS THERAPEUTIC AGENTS FOR THE TREATMENT OF BONE CONDITIONS<br/>[FR] ARYLE-ALKYLE SULFONAMIDES UTILISES EN TANT QU'AGENTS THERAPEUTIQUES POUR LE TRAITEMENT DE PATHOLOGIES OSSEUSES
  申请人：UNIV ABERDEEN

  公开号：WO2005118528A3

  公开（公告）日：2006-01-26
• ARYL ALKYL SULFONAMIDES AS THERAPEUTIC AGENTS FOR THE TREATMENT OF BONE CONDITIONS
  申请人：The University Court of The University of Aberdeen

  公开号：EP1756046A2

  公开（公告）日：2007-02-28
• US7964643B2
  申请人：——

  公开号：US7964643B2

  公开（公告）日：2011-06-21
• Development and Characterization of Biphenylsulfonamides as Novel Inhibitors of Bone Resorption
  作者：Iain R. Greig、Aymen I. Idris、Stuart H. Ralston、Rob J. van't Hof

  DOI：10.1021/jm051236m

  日期：2006.12.1

  Increased osteoclastic bone resorption plays a central role in the pathogenesis of many bone diseases, and osteoclast inhibitors are the most widely used treatments for these diseases. We have identified and characterized a series of novel biphenylsulfonamide derivatives that have potent inhibitory effects on osteoclastic bone resorption in vitro and that prevent ovariectomy-induced bone loss in vivo. A number of aromatic substituted derivatives were prepared and a QSAR model was generated, which allowed accurate prediction of compound potency. Using this model, we have prepared compounds able to inhibit osteoclast formation and bone resorption in vitro at concentrations in the nanomolar range. One such compound, 55 (ABD295) (Greig, I. R.; Mohamed, A. I.; Ralston, S. H.; van't Hof, R. J. Alkyl Aryl Sulfonamides as Therapeutic Agents for the Treatment of Bone Conditions. GB Patent WO2005118528, 2005), fully reversed ovariectomy-induced bone loss in mice at a dose of 5 (mg/kg)/day. In conclusion, biphenylsulfonamides like 55 form a new class of potent antiresorptive agents with possible therapeutic use in diseases characterized by increased bone resorption.