(E)-2-(naphthalen-1-yl)ethenesulfonamide | 134640-92-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-2-(naphthalen-1-yl)ethenesulfonamide
• 英文别名: 2-(1-naphthyl)ethenesulfonamide；(E)-2-naphthalen-1-ylethenesulfonamide
• CAS: 134640-92-9
• 化学式: C₁₂H₁₁NO₂S
• 分子量: 233.291
• InChiKey: HUWOVSGCPOMFRR-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(naphthalen-1-yl)ethenesulfonamide 、 4,6-二氯-5-(2-甲氧基苯氧基)-2,2'-二嘧啶 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 以80%的产率得到(E)-N-[6-chloro-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]-2-(naphthalen-1-yl)ethenesulfonamide
  参考文献：
  名称：

  Ethenesulfonamide and ethanesulfonamide derivatives, a novel class of orally active endothelin-A receptor antagonists

  摘要：

  In the previous paper, we described a series of 2-phenylethenesulfonamide derivatives, a novel class of ET(A)-selective endothelin (ET) receptor antagonists, including the 2-methoxyethoxy derivative 2a and the 2-fluoroethoxy derivative (2b). In this paper, we wish to report further details of structure-activity relationships (SARs) of the two regions of the molecule in compound 2b, which were the alkoxy region at the 6-position of the core pyrimidine ring and the 2-phenylethenesulfonamide region. In these modifications, replacement of the 2-fluoroethoxy group with a methoxy group (6e) and replacement of the 2-phenylethenesulfonamide group with a 2-(pyridin-3-yl)ethenesulfonamide group (61) or 2-phenylethanesulfonamide group (6q) were well tolerated both in the ET(A) binding affinity and ET(A) selectivity. Among them, compound 6e showed further improvement in oral activity compared to 2b. After oral administration, compound 6e inhibited the big ET-1 induced pressor response in conscious rats at 0.3 mg/kg with a duration of >6.5 h. Compound 6e also exhibited a potent antagonistic activity in the pithed rats. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00187-0
• 作为产物：
  描述：

  乙烯磺酰胺 、 1-溴代萘 在 palladium diacetate 、 三苯基膦 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以72%的产率得到(E)-2-(naphthalen-1-yl)ethenesulfonamide
  参考文献：
  名称：

  Palladium-Catalyzed Synthesis ofN-Benzoyl-2-arylethenesulfonamides from [2-(Benzoylsulfamoyl)ethyl]pyridinium Chloride and Aryl Halides

  摘要：

  描述了一种新的通用合成方法，通过在醋酸钯的存在下，将芳基卤化物（包括杂芳基卤化物）与[2-(苯甲酰磺酰氨基)乙基]吡啶盐酸盐反应，合成N-苯甲酰-2-芳基乙烯磺酰胺。

  DOI：

  10.1246/bcsj.64.1431

文献信息

• HIROOK, SYUZI;TANBO, YUZI;TAKEMURA, KATSUYA;NAKAHASHI, HIRONORI;MATSUOKA,+, BULL. CHEM. SOC. JAP. , 64,(1991) N, C. 1431-1433
  作者：HIROOK, SYUZI、TANBO, YUZI、TAKEMURA, KATSUYA、NAKAHASHI, HIRONORI、MATSUOKA,+

  DOI：——

  日期：——