(3R,4S)-(+)-N-[3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)-chroman-4-yl]-N-methyl-methanesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (3R,4S)-(+)-N-[3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)-chroman-4-yl]-N-methyl-methanesulfonamide
• 英文别名: trans-N-[3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)-chroman-4-yl]-N-methyl-methanesulfonamide；(+/-)-trans-N-[3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)-chroman-4-yl]-N-methyl-methanesulfonamide；N-[3-Hydroxy-2,2-dimethyl-6-(4,4,4-trifluoro-butoxy)-chroman-4-yl]-N-methyl-methanesulfonamide；N-[3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)-3,4-dihydrochromen-4-yl]-N-methylmethanesulfonamide
• 化学式: C₁₇H₂₄F₃NO₅S
• 分子量: 411.442
• InChiKey: SRZRLJWUQFIZRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  84.4
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3R,4S)-(+)-N-[3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)-chroman-4-yl]-N-methyl-methanesulfonamide 在 乙酸酐 作用下， 以 吡啶 为溶剂， 生成 (+/-)-trans-N-[3-acetoxy-6-(4,4,4-trifluorobutoxy)-2,2-dimethylchroman-4-yl]-N-methyl-methanesulfonamide
  参考文献：
  名称：

  Sulfonamide-substituted benzopyran derivatives, processes for their

  摘要：

  磺胺基取代的苯并吡喃衍生物，其制备方法，其作为药物的用途，以及包含它们的药物制剂。具有如下式I的化合物 ##STR1## 其中在索赔中指示的取代基的含义，是用于预防和治疗心血管疾病，特别是心律失常，用于治疗胃肠道溃疡或腹泻疾病的药物的杰出活性物质。

  公开号：

  US06008245A1
• 作为产物：
  描述：

  N-甲基甲磺酰胺 、 2,2-Dimethyl-6-(4,4,4-trifluorobutoxy)-1a,7b-dihydrooxireno[2,3-c]chromene 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 生成 (3R,4S)-(+)-N-[3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)-chroman-4-yl]-N-methyl-methanesulfonamide
  参考文献：
  名称：

  Synthesis and Activity of Novel and Selective I_Ks-Channel Blockers

  摘要：

  Since the discovery of the I-Ks-potassium channel as the slowly activating component of the delayed rectifier current (I-k) in cardiac tissue, the search for blockers of this current has been intense. During the screening of K-ATP-channel openers of the chromanol type we found that chromanol 293B was able to block I-Ks. Chromanol 293B is a sulfonamide analogue of the K-ATP-channel openers but had no activity on this target. Experiments were initiated to improve the activity and properties based on this lead compound. As a screening model we used Xenopus oocytes injected with human minK (KCNE1). Variations of the aromatic substituent and the sulfonamide group were prepared, and their activity was evaluated. We found that the greatest influence on activity was found in the aromatic substituents. The most active compounds were alkoxy substituted. We chose HMR1556 ((3R, 4S)-(+)-N-[-3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)chroman-4-yl]-N-methyl-ethanesulfonamide) 10a for development as an antiarrhythmic drug. The absolute configuration, resulting from an X-ray single-crystal structure analysis, was determined.

  DOI：

  10.1021/jm0109255

文献信息

• Use of inhibitors of the KQT1 channel and methods of controlling and treating diseases caused by helminths and ectoparasites
  申请人：Aventis Pharma Deutschland GMBH

  公开号：US20020055537A1

  公开（公告）日：2002-05-09

  Use of inhibitors of the KQT1 channel for preparing a medicament for treating diseases caused by helminths and ectoparasites Inhibitors of the KQT1 channel are a novel way of destroying helminths and ectoparasites. For this reason, blockers of the cellular KQT1 channel, which is present in helminths and ectoparasites, are used for preparing a medicament for the treatment of vertebrates and humans infested by helminths or ectoparasites. These KQT1 blockers are used as medicaments on their own or in combination with other medicaments and therapeutic measures. Inhibitors of the KQT1 channel are likewise a novel mechanism of action for phytoparasites such as insects, arachnids, molluscs and nematodes, and consequently, they are used for preparing a crop protection composition.

  使用 KQT1 通道抑制剂制备治疗蠕虫和体外寄生虫引起的疾病的药物 KQT1 通道抑制剂是消灭蠕虫和体外寄生虫的一种新方法。因此，蠕虫和体外寄生虫体内的细胞 KQT1 通道阻断剂可用于制备治疗脊椎动物和人类蠕虫或体外寄生虫疾病的药物。这些 KQT1 阻断剂可单独用作药物，也可与其他药物和治疗措施结合使用。 KQT1 通道抑制剂同样也是一种针对植物寄生虫（如昆虫、蛛形纲动物、软体动物和线虫）的新型作用机制，因此可用于制备作物保护组合物。
• Sulfonamid-substituierte Benzopyranderivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP0913396B1

  公开（公告）日：2003-09-17
• VERWENDUNG VON INHIBITOREN DES KQT1-KANALS ZUR HERSTELLUNG EINES MEDIKAMENTS ZUR BEHANDLUNG VON KRANKHEITEN, DIE DURCH HELMINTHEN UND EKTOPARASITEN HERVORGERUFEN WERDEN
  申请人：Sanofi-Aventis Deutschland GmbH

  公开号：EP1140042B1

  公开（公告）日：2008-03-26
• US6008245A
  申请人：——

  公开号：US6008245A

  公开（公告）日：1999-12-28
• US6335363B1
  申请人：——

  公开号：US6335363B1

  公开（公告）日：2002-01-01