乙烯磺酰胺,2-(3-吡啶基)-,(1E)- | 134640-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 乙烯磺酰胺,2-(3-吡啶基)-,(1E)-
• 英文名称: 2-(3-pyridyl)ethenesulfonamide
• 英文别名: (E)-2-(pyridin-3-yl)ethenesulfonamide；(E)-2-pyridin-3-yl-ethenesulfonic acid amide；(E)-2-pyridin-3-ylethenesulfonamide
• CAS: 134640-94-1
• 化学式: C₇H₈N₂O₂S
• 分子量: 184.219
• InChiKey: AMNPOVSVFKTFRY-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙烯磺酰胺,2-(3-吡啶基)-,(1E)- 、 波生坦中间体(I) 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 以62%的产率得到(E)-N-[6-chloro-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]-2-(pyridin-3-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：

  (E)-2-pyridin-3-yl-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以73%的产率得到乙烯磺酰胺,2-(3-吡啶基)-,(1E)-
  参考文献：
  名称：

  Heteroarylethenyl derivatives, their manufacture and use as pharmaceutical agents

  摘要：

  本发明涉及公式I的化合物，其中R1、R2和R3在此定义，它们的药学上可接受的盐、对映体形式、非对映异构体和混合物，上述化合物的制备，含有它们的药物以及它们的制造，以及上述化合物在控制或预防癌症等疾病方面的用途。

  公开号：

  US20070010564A1

文献信息

• Palladium-Catalyzed Synthesis of<i>N</i>-Benzoyl-2-arylethenesulfonamides from [2-(Benzoylsulfamoyl)ethyl]pyridinium Chloride and Aryl Halides
  作者：Syuzi Hirooka、Yuzi Tanbo、Katsuya Takemura、Hironori Nakahashi、Tsuyoshi Matsuoka、Shigeyasu Kuroda

  DOI：10.1246/bcsj.64.1431

  日期：1991.4

  A new, general synthesis of N-benzoyl-2-arylethenesulfonamides by the reaction of aryl halides including heteroaryl halides with [2-(benzoylsulfamoyl)ethyl]pyridinium chloride in the presence of palladium acetate is described.

  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。
• 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：——
• HETEROARYLETHENYL DERIVATIVES, THEIR MANUFACTURE AND USE AS PHARMACEUTICAL AGENTS
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1904471B1

  公开（公告）日：2009-10-21
• US7208506B2
  申请人：——

  公开号：US7208506B2

  公开（公告）日：2007-04-24
• Ethenesulfonamide and ethanesulfonamide derivatives, a novel class of orally active endothelin-A receptor antagonists
  作者：Hironori Harada、Jun-ichi Kazami、Susumu Watanuki、Ryuji Tsuzuki、Katsumi Sudoh、Akira Fujimori、Masanao Sanagi、Masaya Orita、Hideaki Nakahara、Jun Shimaya、Shin-ichi Tsukamoto、Akihiro Tanaka、Isao Yanagisawa

  DOI：10.1016/s0968-0896(01)00187-0

  日期：2001.11

  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.