N-(6-Nitro-benzo[1,3]dioxol-5-ylmethyl)-methanesulfonamide | 1026627-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N-(6-Nitro-benzo[1,3]dioxol-5-ylmethyl)-methanesulfonamide
• 英文别名: N-[(6-nitro-1,3-benzodioxol-5-yl)methyl]methanesulfonamide
• CAS: 1026627-30-4
• 化学式: C₉H₁₀N₂O₆S
• 分子量: 274.254
• InChiKey: QGIOITZHKRKEOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(6-Nitro-benzo[1,3]dioxol-5-ylmethyl)-methanesulfonamide 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 N-(4-chloro-3-methyl-5-isoxazolyl)-2-[3,4-(methylenedioxy)-6-methanesulfonylaminomethyl]phenylaminocarbonyl-3-thiophenesulfonamide
  参考文献：
  名称：

  Structure−Activity Relationships of N ²-Aryl-3-(isoxazolylsulfamoyl)-2-thiophenecarboxamides as Selective Endothelin Receptor-A Antagonists

  摘要：

  We report here that N-2-aryl-3-(isoxazolylsulfamoyl)-2-thiophenecarboxamides are potent and selective small molecule ETA receptor antagonists. The aryl group was subjected to extensive structural modification. With monosubstitution, the para position was most useful in increasing potency, with methyl being preferred. With disubstitution, 2,4-disubstitution further enhanced activity with methyl or cyano groups being preferred at the 2-position. In this series, a benzo-[d][1,3]dioxole group is equivalent to a 4-methyl group in in vitro activity and afforded the compounds with both in vivo activity and moderate half-lives.

  DOI：

  10.1021/jm9608366
• 作为产物：
  描述：

  3,4-亚甲二氧基苄胺 在 硝酸 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 N-(6-Nitro-benzo[1,3]dioxol-5-ylmethyl)-methanesulfonamide
  参考文献：
  名称：

  Structure−Activity Relationships of N ²-Aryl-3-(isoxazolylsulfamoyl)-2-thiophenecarboxamides as Selective Endothelin Receptor-A Antagonists

  摘要：

  We report here that N-2-aryl-3-(isoxazolylsulfamoyl)-2-thiophenecarboxamides are potent and selective small molecule ETA receptor antagonists. The aryl group was subjected to extensive structural modification. With monosubstitution, the para position was most useful in increasing potency, with methyl being preferred. With disubstitution, 2,4-disubstitution further enhanced activity with methyl or cyano groups being preferred at the 2-position. In this series, a benzo-[d][1,3]dioxole group is equivalent to a 4-methyl group in in vitro activity and afforded the compounds with both in vivo activity and moderate half-lives.

  DOI：

  10.1021/jm9608366

文献信息

• Structure−Activity Relationships of <i>N</i> ²-Aryl-3-(isoxazolylsulfamoyl)-2-thiophenecarboxamides as Selective Endothelin Receptor-A Antagonists
  作者：Chengde Wu、Ming F. Chan、Fiona Stavros、B. Raju、Ilya Okun、Rosario S. Castillo

  DOI：10.1021/jm9608366

  日期：1997.5.1

  We report here that N-2-aryl-3-(isoxazolylsulfamoyl)-2-thiophenecarboxamides are potent and selective small molecule ETA receptor antagonists. The aryl group was subjected to extensive structural modification. With monosubstitution, the para position was most useful in increasing potency, with methyl being preferred. With disubstitution, 2,4-disubstitution further enhanced activity with methyl or cyano groups being preferred at the 2-position. In this series, a benzo-[d][1,3]dioxole group is equivalent to a 4-methyl group in in vitro activity and afforded the compounds with both in vivo activity and moderate half-lives.