2,2-dimethyl-6-propoxy-3H-chromen-4-one | 1027299-00-8

• 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: 2,2-dimethyl-6-propoxy-3H-chromen-4-one
• CAS: 1027299-00-8
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: MMSRGCNVTSUNCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-6-propoxy-3H-chromen-4-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 2,2-Dimethyl-6-propoxy-3,4-dihydrochromen-4-ol
  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
• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 四氢吡咯 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.0h， 生成 2,2-dimethyl-6-propoxy-3H-chromen-4-one
  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

• Synthesis and Activity of Novel and Selective I_Ks-Channel Blockers
  作者：Uwe Gerlach、Joachim Brendel、Hans-Jochen Lang、Erich F. Paulus、Klaus Weidmann、Andrea Brüggemann、Andreas E. Busch、Hartmut Suessbrich、Markus Bleich、Rainer Greger

  DOI：10.1021/jm0109255

  日期：2001.11.1

  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.